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1,8-Naphthalimide-based fluorescent
chemosensors: recent advances and perspectives
Cite this: J. Mater. Chem. C, 2020,
8, 13501
Hong-Qiang Dong,a Tai-Bao Wei, *a Xiao-Qiang Ma,a Qing-Yu Yang,a
Yun-Fei Zhang,a Yu-Jiao Sun,a Bing-Bing Shi,a Hong Yao, a You-Ming Zhang ab

and Qi Lin *a

1,8-Naphthalimide, as one of the classical dyes and fluorophores, has been widely used in analytical
Received 3rd August 2020, chemistry, materials chemistry, and biochemistry fields because of its excellent characteristic
Accepted 9th September 2020 photostability, good structural flexibility, high fluorescence quantum yield, and large Stokes shift. This
DOI: 10.1039/d0tc03681a review mainly focuses on 1,8-naphthalimide and its derivatives in ion detection, molecular recognition,
material applications, and bioimaging in the past five years. Simultaneously, we hope to develop more
rsc.li/materials-c powerful fluorescent chemosensors for broad and exciting applications in the future.

1. Introduction
More recently, the research on toxic ions and biological molecular
sensing,1–3 organic optoelectronic materials,4 high-performance
gels, and bioimaging applications have increasingly attracted the
attention of researchers.5–7 To date, great achievements have been
made in electrochemical detection,8 spectrophotometry,9 element
analysis,10 and chromatography.11,12 However, there are also a few
challenges in these methods, which include low accuracy, poor Fig. 1 (a) Chemical structure of 1,8-naphthalimide, (b) the application of
1,8-naphthalimide-based fluorescent chemosensors.
qualitative ability, expensive, and time-consuming. Fluorescent
techniques have attracted considerable research interests com-
pared with the above detection methods owing to their advantages
of low cost, fast response, noteworthy sensitivity, and simple We can see that the naphthalene ring acts as a p bridge, R1 is an
operation.13,14 Therefore, it has become the main detection electron-donating group (such as –NH2 and –OH), the imide
methods and has been widely used in biochemistry, chemistry, part acts as an electronic group constituting the D–p–A system,
medicine, and other fields.15–17 and 1,8-naphthalimide is also an electron-deficient system.27–30
1,8-Naphthalimide (NI), naphthalene diimide (NDI), pery- On the other hand, because of its outstanding light/thermal
lene bisimide (PBI), and their derivatives play a key role in the stability, it has become an important organic functional
field of fluorescent materials and dyes.18–21 In addition, the material.31–34 Moreover, the fluorescence colour will show
special structure of NI, NDI, and PBI endows them excellent changes accordingly when different substitutions are intro-
properties, high electron affinity, as well as good thermal duced at the 4-position base. At the same time, the above
stability and oxidation stability, which has led to their develop- mechanisms have been well-confirmed through theoretical
ment and application receiving widespread attention.22–24 calculations.35–37 Based on these characteristics, this scaffold
Naphthalimide, as the ‘‘simplest’’ molecule, has better water has found wide applications in the development of fluorescent
solubility than other molecules such as NDI and PBI. Therefore, chemosensors in the fields of molecular recognition, molecular
the study of naphthalimide derivatives has become a hot topic. imaging, bioorganic chemistry, analytical chemistry, materials
The structure of 1,8-naphthalimide is as shown in Fig. 1(a).25,26 chemistry, as well as in the biological and medical science
communities.38–40
However, naphthalimide-based fluorescent chemical sensors
a
Key laboratory of Polymer Materials of Gansu Province, College of Chemistry and
have not been reviewed. Although the research progress of
Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070,
P. R. China. E-mail: weitaibao@126.com, linqi2004@126.com
naphthalimide in ionic and biological aspects has been reviewed
b
Deputy Director-General of Gansu Natural Energy Research Institute, before,41,42 it has not been systematically summarized. In particular,
Renmin Road 23, Lanzhou, Gansu, 730070, P. R. China the rapid development of optoelectronic materials in recent years

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has made naphthalimide the most brilliant star among classical

fluorophores.43 Therefore, it is necessary to summarize the
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various applications based on 1,8-naphthalimide and its

derivatives. In this review, we mainly introduce the chemo-
sensors and material applications of 1,8-naphthalimide in
the past five years, which include ion detection, molecular
recognition, material preparation, and bioimaging (Fig. 1(b)).
We are hoping for the development of more powerful fluorescent Fig. 3 Possible binding mode of sensor 2 with Fe3+ and CN .
chemosensors for broad and exciting applications in the future.

1.52  10 7 M, and DFT and 1H NMR studies supported the

2. Ion detection complexing constant of 1 : 1. Meanwhile, if the strong chelating
agent EDTA is added to complex Al3+, the solution will return to
The detection of ions is paramount in chemistry because
the original form and there is no interference from other metal
of their involvement in various physiological processes; for
ions in these processes.
example, iron, the most important trace element in the human
In 2017, Wei et al. synthesized a water-soluble fluorescent
body, is involved in a number of electrons transfer as well as
chemical sensor (2) based on 1,8-naphthalimide derivatives as
oxidoreductase processes. However, excessive intake of iron
a new type of fluorescent sensor that continuously detects
ions can lead to an increased risk of liver cancer and neuro-
Fe3+ and CN (Fig. 3).49 The chemical sensor 2 has excellent
logical diseases.44,45 Of course, apart from the detection of ions
fluorescence specific selectivity and high sensitivity to Fe3+ ions
in the body, the detection of toxic ions from the outside world is
in pure water. In addition, in the same medium, the complex of
also extremely important. Mercury is one of the well-known
2 and Fe3+ (2-Fe3+) was more sensitive to CN than other
heavy toxic metals. It can exist in different forms such as its
anions, which forms an on–off–on fluorescence recognition
elemental state, as well as organic and inorganic forms. This
system. The LOD of sensor 2 for Fe3+ was 1.97  10 7 M and
pollutant may be gradually concentrated through the food
the LOD of 2-Fe3+ complex for CN was 2.6  10 10 M. More
chain even at imperceptible trace levels, posing a threat to
importantly, the recognition of the complexes by the Fe3+
human health46,47 Therefore, it is necessary to develop a novel
sensor 2 and CN can be successfully applied in pure water.
chemosensor for detecting metal ions and highly toxic ions
This also provides a new concept for the detection of naphthal-
with high sensitivity.
imide in pure water phase.
2.1 Cation detection Soon after, they rationally designed and reported a water-
soluble, easy-to-make, and efficient Fe3+ fluorescence sensor 3
Al is one of the most abundant elements in the earth’s crust
(Fig. 4).50 By introducing a carboxyl group into 1,8-naphthal-
due to its light weight and corrosion resistance. It is widely
imide, the water solubility of the sensor was increased. The
used in various industries and food packaging. However,
chemical sensor has good solubility in water and specific
excessive Al3+ can cause pathological changes in the body.
fluorescence selectivity for Fe3+ and H2PO4 in water. The
For example, patients with kidney failure cannot normally
LOD of Fe3+ and H2PO4 was 4.97  10 7 M and 5.27  10 6 M,
discharge aluminum from the body, which can cause loss of
respectively. Other ions have no significant effect in their
memory, renal insufficiency, and aluminum poisoning. There-
sensing behaviour. Interestingly, sensor 3 could not only serve
fore, the detection of Al3+ has become increasingly important.
as a reversible Fe3+ sensor but also as a fluorescent switch
Sahoo et al. (2018) designed a high-selectivity sensor (1) for
controlled by Fe3+ and H2PO4 . Under ultraviolet light (365 nm),
detecting Al3+ (Fig. 2).48 The sensor could detect Al3+ accom-
the colour of the light changes significantly and the rapid
panied by fluorescence ‘‘turn on’’ and a blue shift in the
reversible fluorescence change could be observed with the naked
absorbance in DMSO : H2O (1 : 1, v/v) solution. The light brown
eye. This switching process can be repeated multiple times with
color becomes colorless, the lowest detection limit (LOD) was
little fluorescence loss.
In 2018, Qiu et al. prepared a multifunctional copolymer
sensor (4) containing rhodamine 6G and 1,8-naphthalimide

Fig. 2 Structure of the fluorescent chemosensor 1. Fig. 4 Structure of the fluorescent chemosensor 3.

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Fig. 7 (a) Proposed mechanism for the detection of Cu2+ ion, (b) fluores-
Fig. 5 Structure of the fluorescent chemosensor 4.
cence photographs of the sensor in the absence (left) and presence (right)
of Cu2+ in a dark-box ultraviolet analyzer when excited at 365 nm.

group by the reversible addition–fragmentation free radical

polymerization method. The sensor could effectively detect phenomenon. Meanwhile, the color of the solution of 6 in
Fe3+ under the control of pH (Fig. 5).51 After adding acid, changed from yellow to blue. The LOD of sensor 6 for Cu2+ was
rhodamine 6G and 1,8-naphthalimide groups undergo fluores- 3.26  10 8 M, which achieved a highly sensitive level.
cence resonance energy transfer (FRET) and emit red fluores- Thereafter, a large number of naphthalimide-based Cu2+-
cence; with the addition of Fe3+, the distance between the selective fluorescent sensors were reported.54,55 Xu et al. (2017)
rhodamine 6G and 1,8-naphthalimide groups is reduced, FRET reported a Cu2+ probe (7) with 1,8-naphthalimide hydrazone
is suppressed, photoinduced electron transfer (PET) is generated, derivatives modified by pyrrole units (Fig. 8).56 The sensor uses
and green fluorescence is emitted, which provides another a unique hydrolysis mechanism to achieve high selectivity and
method based on the 1,8-naphthalimide ion and performance. highly sensitive detection of Cu2+ in CH3CN/H2O (v/v = 9 : 1,
Later, Fu et al. had prepared a highly selective fluorescent pH = 7.40) solution. When copper ions are added, the color of
chemical sensor (5), which establish a method for detecting the solution becomes colorless and the fluorescence changes
cobalt(II) ions by using a visual colorimetric response to initiate from red to blue-green. At the same time, the complex ratio
a fluorescence enhancement (Fig. 6).52 In CH3CN/HEPES was calculated to be 1 : 1 and the LOD was 1.50  10 7 M.
(4 : 1, v/v, pH = 7.4) solution, the sensor emits almost no In addition, the hydrolysis mechanism of Cu2+ to promote the
fluorescence (‘‘off’’ state), which is due to the energy level electrophilic substitution was verified by 1H NMR. This
difference of PET caused by the electron-rich amide group new mechanism has created a new research method for new
towards the naphthalimide fluorophore, causing the PET and fluorescent probes.
intramolecular charge transfer (ICT) processes in a dark state; In 2018, Wu et al. designed a fluorescent sensor (8) based on
the addition of Co2+ allows the synergy with the sensor (5) nitrilotriacetic acid-functionalized 1,8-naphthalimide, which
receptor unit to suppress the PET and ICT processes, which was constructed by a reverse PET mechanism to detect Cu2+
directly leads to strong local emissions in the blue band with high selectivity (Fig. 9).57 The author introduced methyl
(‘‘on’’ state), the colour changes from pink to colorless, and acrylate hydrolysis into the system. The methyl acrylate hydro-
the Job-plot analysis shows that the complex ratio is 1 : 1 and lysis group not only increased the solubility of sensor 8 but
LOD is 0.26  10 7 M. In addition, the author also uses the could also serve as a receptor group. It laid the foundation for
sensor for environmental detection, thus expanding the sensor the production of PET. The sensor could detect Cu2+ by
application. fluorescence quenching in solution and the LOD was 4.67 
In 2016, Wang et al. designed two chemical sensors (6) based on 10 8 M. This also provides another method for detecting ions.
thiosemicarbazide or semicarbazide functionalized 1,8-naphthal- After that, Li et al. (2020) designed and reported a sensor (9)
imide derivatives (Fig. 7).53 The sensor 6 could detect Cu2+ (Fig. 10)58 by introducing 2-(2-aminoethoxy)ethanol to improve
with high selectivity in (MeCN–H2O) medium with a blue shift the hydrophilicity. Schiff base, as a polydentate ligand of Cu2+,
could also detect Cu2+ with high selectivity by turning off the
fluorescence. The addition of Cu2+ leads to the generation of

Fig. 6 (a) Proposed mechanism for the detection of Co2+ ion, (b) the
UV-vis absorption spectrum of sensor 5 (1  10 5 mol L 1) and upon the Fig. 8 (a) The structure of probe 7, (b) the ultraviolet photo of probe 7 and
addition of salts. with Cu2+, (c) the fluorescent photo of probe 7 and with Cu2+.

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Fig. 11 The structures of the fluorescent sensors 10–12.

Fig. 9 The proposed binding mode of the fluorescence quenching of

sensor 8 with Cu2+ based on the reverse-PET mechanism.

Fig. 12 The proposed mechanism of 13 bonding with Hg2+.

was 2.8  10 7 M. In 2015, Arami et al. obtained a 4-amino-

1,8-naphthyl-conjugated polyamideamine dendrimer (11) by
reacting 4-amino-1,8-naphthalic anhydride with a polyamino-
amine dendrimer (Fig. 11b).63 The detection of Ag+ in the
H2O/DMF (4 : 1, v/v) solution, which was mainly through
the formation of the PET process with the metal cations
in the solution, causes the fluorescence to be quenched to
achieve the detection of silver ions, and other cations show little
interference in the detection. Subsequently, Ye et al. designed
and synthesized two chemical sensors based on naphthalimide
(12A) and (12B) (Fig. 11c).64 Through the ability to coordinate
Fig. 10 (a) The proposed structure of sensor 9-Cu2+ complex and its
intramolecular PET process, (b) fluorescence responses of sensor 9 to
with the amide group and the imidazole group, the fluorescence
various metal ions. quenching detection of Hg2+ in phosphate buffer can be per-
formed and the fluorescence quenching rate can reach 90%
with the formation of the proton-mercury complex. Also, the
PET in the molecule; the study found that the complex ratio of sensor can detect Hg2+ ions in a wide pH range (7.0–10.0).
the sensor to Cu2+ is 2 : 1 and the LOD was 3.74  10 8 M. At the In 2017, Wei et al. designed a simple water-soluble chemical
same time, when the chelating agent EDTA is added, it can sensor (13), which uses carboxyl groups and imidazole groups
complex copper ions well and the cycle can reach 4 times. as hydrophilic groups, and serves as an Hg2+ binding site65
Moreover, the changes in the fluorescence of (9) resulting (Fig. 12). The fluorescence quantum yield of sensor (13) in
from the addition of Cu2+ and EDTA were utilized to form a water is 56% with quinine hemi-sulfate salt as a reference. The
molecular NAND logic gate. addition of mercury ions can perform fluorescence quenching
Among toxic metals, Pb2+, Ag+, and Hg2+ remain one of the and the LOD was 1.785  10 7 M. In addition, when I ions are
foremost threats to human health. Therefore, it is necessary to added, Hg2+ ions are complexed and the circulation is up to
prepare a sensor that can efficiently detect highly toxic metal 5 times. This also provides a method for multi-substrate
ions.59–61 Zhou et al. (2016) reported a ratiometric two-photon analysis to detect the ions.
fluorescent probe, which was based on the D–p–A-structure Next, they introduced a new fluorescent chemical sensor (14)
two-photon fluorophore of the naphthalimide derivative and by introducing glutathione into 1,8-naphthalimide (Fig. 13).66
the deprotection of aryl propargyl ethers by the palladium The sensor could detect iron and mercury ions with high
species (10) (Fig. 11a).62 The probe introduces 3-bromo- selectivity and the response time is less than 10 seconds, while
propargyl into 1,8-naphthalimide to form a D–p–A structure the LOD was 7.92  10 8 M and 4.22  10 8 M, respectively.
two-photon fluorophore-based naphthalimide derivative, which The test strips based on (14) were prepared, which could
can increase the detection of Pd2+ by 25 times. When adding conveniently and efficiently detect Fe3+ and Hg2+.
Pd2+ to the H2O/DMSO (99 : 1, v/v) solution, the colour of Europium, as the most active metal among rare earth
the solution changes from white to yellow, along with the elements, is widely used in electronic displays, LEDs, medical
fluorescence colour changes from blue to yellow; the LOD treatment, etc., as a red fluorescent powder for color TV

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Fig. 13 (a) The structure of sensor 14, (b) fluorescence emission data of
sensor 14 and different metal ions in solution.
Fig. 15 Illustration of the chloride-binding process of the aryl-triazole
foldamer 17 in the presence of anions.

found to decrease to varying degrees. Through 1H NMR, 1H–1H

NOESY measurements, and fluorescence titration experiments,
it was found that the fluorescence quenching phenomenon was
due to the partially anion-induced aggregation of naphthalimide,
resulting in a foldamer, and the coordination ratio was 1 : 1.
In the same year, Kubo et al. reported a 1-hydroxy-2,3,1-
Fig. 14 (a) Synthetic routes of 15 and 16 ligands and their Eu, Gd
benzodiazaborine conjugated with 1,8-naphthalimide (18)
complexes, (b) ball-and-stick representation of the crystal structures of
15 and 16, (c) the coordination polyhedra of 15 and 16.
(Fig. 16).77 The result indicated that its fluorescence characteristics
are greatly affected by the nature of the solvent. In particular, in the
solution of DMSO, it has no fluorescence intensity. In this case,
together with ruthenium oxide.67–69 Therefore, the detection when other anions were added to contain 18 DMSO solutions, it
of europium is still a challenge. Yan et al. (2017) designed was found the sensor had a very high selectivity for F . Similarly,
two blue fluorophores (15) and (16), namely, 4-(1,8-naphthal- adding AcO to the THF solution had a very obvious reaction.
imide)pyridine n-oxide (4-nipyno) and 3-(1,8-naphthalimide)- UV-vis titration, nuclear magnetic resonance, and mass spectro-
pyridine n-oxide (3-nipyno) (Fig. 14),70 which are used as metry analysis show that it may be due to the interaction of
auxiliary ligands to enhance the viability of Eu(III) ion lumines- intermolecular hydrogen bonds (Me2SQO and HO–B), which
cence. The ligand consists of a coordinated pyridine n-oxide reduced the aromaticity of the benzodiazaborine macrocycle,
(PyNO) and a substituted bluish 1,8-naphthalimide group in causing an increase in the negative character of boron.
the para and meta positions. Pyridine n-oxide is a strong Lewis Subsequently, the chemical sensors based on naphthal-
base; ligand design makes it possible to use blue organic imide for F detection were synthesized in large quantities.
fluorescent molecules as auxiliary ligands to enhance the Zhu et al. (2017) used benzimidazole and 1,8-naphthalimide as
possibility of the red emission of Eu(III) ions. The luminescence raw materials to synthesize a novel fluoride ion colorimetric
quantum yields of (15) and (16) were 41.5% and 28.6%, fluorescent probe (19) by Schiff Base reaction (Fig. 17a).78 The
respectively. This auxiliary ligand design strategy makes the probe can be used to detect fluoride ions in acetonitrile
blue chromophore a luminous sensitizer for Eu(III) ions and can solution with naked eyes. When the fluoride ion solution is
efficiently detect Eu(III) ions. added, the original solution’s colour turns from yellow to blue
and the fluorescence is red-shifted. The LOD was 0.41  10 6 M.
2.2 Anion detection The 1H NMR titration and theoretical calculation based on

Due to the important role of anions in biology and environment,

designing an easily-synthesized anion sensing and recognition
system has become a research hot topic in the field of ion
detection. However, some anions are very toxic, such as CN
and F , although they have great applications in other aspects;
they are very toxic and seriously endanger the health. Therefore,
the design and development of chemical sensors based on the
detection of anions are still of great significance.71–75
In 2017, Jiang et al. designed a novel chemosensor (17),
which was prepared by the introduction of the aryl-triazole
derivative based on the 1,8-naphthalimide motif (Fig. 15).76
Chloride, bromide, iodide, and other spherical halide anions were
selected as guest ions for anion binding studies. In this research,
when spherical halide anions were added, the fluorescence was Fig. 16 Possible reactions of 18 with AcO in THF and F in DMSO.

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Fig. 17 (a) The proposed mechanism of 19 bonding with the F , (b) the Fig. 19 (a) The schematic representation of the assembly and disassembly
structures of the fluorescent sensor 19. of the sensor (22)-F, (b) fluorescence emission spectra of sensor 22 in
DMSO/H2O (7.4 : 2.6, v/v) solution in the presence of F and other anions.

TD-DFT indicated that fluoride-induced deprotonation is caused

by hydrogen bonding interactions. Meanwhile, Zhang et al.
synthesized an acylhydrazone-functionalized sensor (20) (Fig. 17b).79
The sensor can deprotonate fluoride ions and cause fluorescence
quenching to efficiently detect the fluoride ions. In addition,
when carbon dioxide was introduced into the solution contain-
ing fluoride ions, it was found that the fluorescence was restored
again; this is because CO2 can react with a small amount of water
to form acids, which can provide protons. This also provides a
possibility for detecting gas by naphthalimide derivatives.
In 2018, Wei et al. synthesized a water-soluble fluorescent
chemical sensor (21); 1,8-naphthalimide was successfully Fig. 20 The proposed mechanism of 23 bonding with F and CN .
functionalized with aromatic carboxyl groups (Fig. 18).80 Through
the mechanism of state change from intramolecular charge
transfer to reversed intramolecular charge transfer (ICT-TICT), Maragani et al. (2016) designed triarylborane-substituted
CN in pure water can be detected selectively and sensitively. naphthalimide fluorescent sensor 23 for the selective detection
The LOD of CN was 1.38  10 8 M and less than 1.9 mmol L 1 of F and CN (Fig. 20).86 The sensor 23 shows maximum
is prescribed by the World Health Organization (WHO). At the red-shifting absorption and fluorescence quenching under the
same time, it shows a rapid response of about 1 s when action of F and CN . The photophysical properties and
identifying CN in pure water. theoretical results indicate that triarylborane and naphthal-
Ultra-sensitive detection,81 aggregation-induced emission,82 imide units have a strong electron transfer capability. The
and aggregation-induced enhanced emission83 are currently LODs of F and CN measured by fluorescence titration were
popular research areas in supramolecular chemistry.84 Wei et al. 2.01  10 10 M and 3.94  10 10 M, respectively, which are far
(2019) prepared an anion-induced assembly, which resulted in an below the maximum detection limits of fluoride and cyanide in
aggregation-induced enhanced emission sensor (22) for the ultra- drinking water as stipulated by the WHO. In addition, the effect
sensitive detection of fluoride ions (Fig. 19).85 The sensor contains of F and CN on the structure of the sensor was also studied
a tripod formamide structure, which can provide strong self- through DFT calculations, and the research results were basically
assembly potential and the naphthalimide group of (22) could consistent with the experiments.
act as an anion–p, p–p interaction site, as well as a fluorescent Gale et al. (2018) reported that a series of naphthalimide-
signal group. By 1H NMR, mass spectrometry, and other functionalized ion acceptor probes 24A–24D were synthesized,
experiments, hydrogen bonding and F–p interactions were proved. which can be used for anion binding and transmembrane
Moreover, the LOD was 8.67  10 9 M and test kits were also made transport (Fig. 21).87 The results show that these compounds
to quickly detect fluoride ions in the environment. have good affinity for Cl and NO3 with moderate to relatively
strong affinity. Compounds 24A–24D promote the reverse
transport of chloride and the symmetrical movement mecha-
nism of Cl /H+/OH into the vesicles. Relative to the trans-
membrane transport activities, these compounds are mainly
determined by their chloride affinity. It was found that the most
active transporter 24A has the highest fluorescent staining
efficiency of live A549 cells, which is non-toxic and has an
anion transport activity that is much higher than that of the
previously reported fluorescent anion transporter. This is very
useful for studying the subcellular localization and pharmaco-
Fig. 18 The proposed mechanism of 21 bonding with CN . kinetics of anion transporters in biological systems.

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Fig. 23 The structure and fluorescence response mechanism of H2O2

Fig. 21 (a) The structures of compounds 1–4, (b) schematic illustration of probe 26.
the assays utilised for measuring the Cl /NO3 antiport using the ISE.

designed a two-photon fluorescent probe (26) (Fig. 23) that

detects H2O2 by the fluorescence method.95 By connecting the
borate to the 1,8-naphthalimide group and attaching an
electron-deficient boronate group to naphthalimide, the fluor-
escent chemoprobes are converted in to the ‘‘A–p–A’’ electronic
structure. This electronic structure determines that the probe
molecule has weak fluorescence emission but after the reaction
of hydrogen peroxide and borate, the borate group becomes a
hydroxyl group (electron donating group) and the electronic
structure of the probe becomes ‘‘D–p–A’’. This leads to the
Fig. 22 Chemical structure of 25 and the proposed sensing mechanism
formation of ICT, which causes the probe to have strong
of HSO3 .
fluorescence emission, thus achieving the rapid detection of
H2O2.
Zhu et al. (2019) reported a logic gate-based fluorescent probe The detection of a toxic formaldehyde (HCHO) pollutant in
(25) that reacts selectively with bisulfite (HSO3 ) by selectively aqueous solutions is of significance because HCHO is widely
responding to pH differences between the intracellular organelles found in aquatic food due to its illicit addition or improper
(Fig. 22).88 The probe detects HSO3 through the regulation of PET storage. Chen et al. (2018) reported a robust hydrophilic
and ICT mechanisms. The probe has high selectivity and sensi- hydrazine-naphthalimide-based chitosan (HN-chitosan)-based
tivity towards HSO3 , and the LOD was 2.07  10 8 M. It is worth polymer probe (27) (Fig. 24).96 It utilizes HCHO and grafted
noting that this probe can be activated by the co-stimulation of low hydrazine-naphthoyl, a specific chemical reaction between the
pH and bisulfite. In addition, it has been proved to be biocompa- amine groups, to trigger the start of the fluorescence reaction;
tible and can be used to monitor HSO3 in the lysosomes of living the detection limit reaches 0.05 ppm and the detection time is
cells. This method shows more practical and outstanding cap- less than 1 min. This ultra-sensitivity, high selectivity, fast
abilities in target monitoring and real-time monitoring, thus response, and wide linear detection range can extend the
providing an effective optical tool for biomarker detection. applications of the sensor successfully to the analysis of food
and water in our daily life. In addition, based on the modular
3. Molecule recognition design principle of polymer probes, this method can be widely
used for the ultra-fast detection of other important pollutants.
Apart from anions and cations, small organic molecules and Subsequently, Zhu et al. also successfully designed a fluores-
biomolecules also play an important role in the industries, cent sensor (28) based on naphthalimide (Fig. 25).97 The sensor
agriculture, medicine, and life.89,90 For example, amino acids are
necessary substances for the human body.91 If they are lacking,
it will cause disease in the body but excessive intake of amino acids
will cause discomfort to the human body.92 At the same time,
nitrophenol compounds also have an irreplaceable role in mining,
military, and other fields93 but a small amount of nitrophenol
compounds can cause explosions and other hazards.94 Therefore,
it is equally important in molecular detection.

3.1 Small molecules

Hydrogen peroxide (H2O2) plays a crucial role in many bio- Fig. 24 HCHO-sensing mechanism of the developed hn-chitosan polymer
logical processes in the human body. In 2016, Lin et al. probe 27.

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Fig. 25 The proposed multiple imaging mechanisms based on the

combination of protonation of nitrogen atom and the aza-Cope arrange-
ment and the structure of probe 28.

connects the homoallylamino group to the naphthalimide

group, reasoned by the protonation of the nitrogen atom. Not
only can formaldehyde molecules can be detected, along with Fig. 27 The structure of sensor 30 and the possible recognition mechanism
the fluorescent change to blue and green, but the pH can also for successively monitoring PA and CN .
be detected efficiently.
Poly-nitroaromatic compound (NACs) is a secondary
chemical explosive that is widely used in various dye and textile emission (AIE) method. First, a tripod host compound sensor
industries. Although there are sensors that detect NACs, these 30 based on a trinaphthalimide derivative was designed and
sensors are not applicable for the trace detection of NACs. synthesized (Fig. 27).99 The sensor can be self-assembled into a
Therefore, the development of chemical sensors for the trace supramolecular system and shows blue AIE. Interestingly, 30
detection of NACs is still a challenge and an opportunity. could selectively detect PA and the LOD was 1.19  10 8 M.
In 2020, Gunnlaugsson et al. reported a fluorescent sensor In this process, the self-assembled supramolecular system is
(29) (Fig. 26).98 It was found that as the water content increases, destroyed, causing fluorescence quenching. More interestingly,
the fluorescence increases and is the greatest when the water the combination of the sensor and PA can also be used for CN
content is 30%. In DMSO/H2O (7 : 3, v/v) binary solution, it was detection; the LOD was 7.45  10 7 M. In addition, the PA and
used to detect picric acid, with the fluorescence quenching. CN test kits were coated on a silicone board by the sensors 30
Fluorescence titration, 1H NMR, and IR experiments verified and 30-PA. These kits can easily and efficiently detect PA or CN .
that it was caused by the intermolecular hydrogen bond formed Recently, a novel AIE supramolecular fluorescence sensor 31
between picric acid and the sensor. In addition, other NACs based on a tripod naphthalimide derivative was reported for the
such as 2,4-DNP, 2-NP, 3-NP, and 4-NP did not have a signifi- highly sensitive detection of explosive analogue PA (Fig. 28).100
cant impact on the detection. The sensor 31 can self-assemble into a supramolecular system
In 2019, Wei et al. reported a simple and effective method for through p–p stacking and hydrogen bonding with strongly blue
the selective and sensitive detection of picric acid (PA) and CN AIE. Interestingly, the sensor 31 has a sensitive and selective
through a novel guest competition control aggregation-induced response towards PA. This detection mechanism was a direct
competitive combination of PA and the sensor. This competi-
tive combination destroys the sensor self-assembly and leads
to fluorescence quenching. The LOD was 4.73  10 8 M.
In addition, the solid powder of the sensor 31 can directly

Fig. 26 The proposed multiple imaging mechanisms based on the

combination of protonation of nitrogen atom and the aza-Cope arrange- Fig. 28 The structure of sensor 31 and the proposed recognition mecha-
ment and the structure of probe 28. nism for PA detection.

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recognize PA without the instrument under natural and ultra-

violet irradiation.
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Phosgene and triphosgene, as readily available chemical

reagents, are also important industrial raw materials for the
production of drugs, dyes, and polymers. However, they are
highly toxic compounds. In severe cases, they can cause coma
and even death, thus seriously endangering public safety.
Therefore, it is very necessary to develop simple detection
and identification methods.
Song et al. (2019) synthesized a novel fluorescent chemical
sensor (32) for the first time, in which 1,8-naphthalimide was
used as a fluorophore and 2-(2-aminophenyl)imidazole was
used as a dual-channel recognition site. (Fig. 29).101 The LOD
of phosgene and triphosgene reached 3.2  10 9 M and 1.9 
10 9 M, respectively. 1H NMR titration experiments show that Fig. 31 (a) The structure of supramolecular polymer monomer 34, (b)
representative photographs of the p-gel (34-G) for the selective fluores-
this is because the 1,8-naphthalimide unit with electron-
cence detection of HBA, ABA, and NBA isomers and after the addition of
withdrawing ability reduces the nucleophilicity of the imidazole o-HBA to the p-gel (34-G).
nitrogen, the primary aniline (–NH2) is a strong nucleophilic
group (NG), sensor (32) is acylated on the main amine by
phosgene and triphosgene, and because chlorocarbonyl is a On combining with phosgene, it produced a significant color change
stronger electrophilic group (EG) than trichlorooxycarbonyl, from deep red to orange and a significant ratio fluorescence
it leads to the difference in time. In addition, the test paper enhancement. In addition, the sensor (33) can quantitatively
prepared with sensor (32) is expected to become a practical gas measure phosgene (0–70 m) with low LOD (2.3  10 9 M) and
phase phosgene detection tool. fast response (o5 min).
Meanwhile, Sheng et al. (2018) also designed an anthracene Wei et al. (2019) designed a novel supramolecular polymer
carboxyl fluorescent chemical sensor (33). The sensor could monomer (34) based on bisnaphthalimide-functionalized
detect phosgene with high selectivity and high sensitivity (Fig. 30).102 pillar[5]arene (Fig. 31).103 A part of naphthalimide in this
monomer provides p–p stacking site, hydrogen bonding site,
and the fluorophore functional group. It could self-assemble
into a stable supramolecular polymer p-gel (34-G) in cyclo-
hexanol. Interestingly, the production of the supramolecular
polymer p-gel (34-G) can distinguish o-aminobenzoic acid,
p-nitrobenzoic acid or its isomers, and other common organic
acids with high selectivity and sensitivity. In addition, (34-G)
xerogel can effectively adsorb p-NBA and separate it from water
with a separation rate of 93.2%. This provides potential for the
detection and separation of aromatic acid isomers in naphtha-
limide with supramolecular polymers.

3.2 Biological molecules

Biomacromolecules are important components of organisms,
such as glycoproteins, lipoproteins, and nuclear proteins. Their
Fig. 29 The sensing mechanism of 32 towards phosgene and triphosgene. movement and changes in the body reflect important life
functions, such as carrying out metabolism to supply energy
and materials needed to maintain life, promoting growth and
development, and producing immune function. In recent years,
biomolecular fluorescence detection has received extensive
attention due to its high requirement in clinical diagnosis.104–106
Fluorine-containing substrates are used to observe the activity
of cancer-related enzymes and explain biological events. Certain
types of glutathione s-transferase (GST), such as Pi-like GST
(abbreviated as GSTP-1), compared with the corresponding
normal tissues, are highly expressed in various human cancer
tissues. The fluorescent sensing of biological molecules has
Fig. 30 The structure and fluorescence response mechanism of phosgene attracted intensive attention. Herein, Inoue et al. (2019) reported
sensor 33. a practical fluorinated GST substrate sensor (35) (Fig. 32a).107

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Fig. 32 (a) The sensing mechanism of 35 for GSTP1-1, (b) the synthesis
and proposed mechanism of probe 36.

The sensor (35) exhibited significant fluorescence enhancement

in the aqueous solution where GSTP1-1 and GSH are present.
These results indicate that sensor (35) is a promising tool for
studying the role of endogenous GSTP1-1 in physiological and
Fig. 34 Chemical structure of fluorescent probe 38 and its reaction
pathophysiological environments. Live cell imaging shows that with H2S.
sensor (35) is mainly activated by endogenous GSTP-1 in living
cells and has the potential to distinguish cancer cells from
normal cells. Soon after, Fu et al. (2020) developed a fluorescent 7-nitro-1,2,3-benzoxadiazolamide attached to a piperazinyl-
probe (36) for sensitively mapping the distribution of endogen- naphthalimide scaffold probe 38 (Fig. 34).110 Probe 38 exhibited
ous biothiols in zebrafish (Fig. 32b).108 The 1,8-naphthalimide excellent performance, with a 68-fold increase in the fluorescence.
scaffold serves as an easily modified fluorophore and the There was a significant deviation in the fluorescence response of
2-thiophenecarbonyl group serves as a recognition group. Probe the mitochondrial-targeted naphthalimide probe 38 and NBD to
(36) exhibited strong emission with large Stokes shift increase detect H2S. Needle 38 exhibits higher sensitivity and selectivity
and the LOD was 1.20  10 7 M. under neutral physiological conditions, and has a lower detection
Polysulfide (H2Sn, n 4 1) plays an important role in the limit for H2S compared to other bio-related analytes such as
physiological functions of the human body. Some pathological biothiols, and the LOD was 2.46  10 9 M.
processes are related to H2S. H2S2 is considered to be a power- Monoamine oxidases exist in the human body in the form of
ful signal sensor recently discovered in the human body. Wang MAO-A and MAO-B, and they play an important role in the
et al. (2016) connected an alkyl morpholine group and a process of oxidative deamination. Wang et al. (2020) developed
2-fluoro-5-nitrobenzoyl group to the 1,8-naphthalimide fluoro- a ratiometric fluorescent probe (39) for the detection of
phore, and designed and synthesized a novel H2S2 solution for monoamine oxidase a (MAO-A) in living cells and zebrafish
the enzyme-targeted colorimetric two-photon fluorescent probe (Fig. 35).111 They have previously reported a probe A for detecting
37 (Fig. 33).109 The probe showed good stability, selectivity, and monoamine oxidase a (MAO-A).112 Compared with the previously
sensitivity (LOD = 1.0  10 10 M) and short response time reported probe A, the length of the probe 39 alkyl group connected
(5 min). This provides a promising method for the detection to the nitrogen atom of 1,8-naphthalimide is different. After
and imaging of lysosomal H2Sn, and is expected to be applied to adding monoamine oxidase a (MAO-A), the fluorescence intensity
biological and pathological research related to H2Sn. ratio (I550/I452) at 550 nm and 452 nm changed by about 186 times.
Yoon et al. (2016) developed a hydrogen sulfide that opens Compared with probe A, it was more reactive and less affected by
mitochondrial targeting based on the selective thiolysis of temperature.
The early diagnosis of ovarian cancer plays an important
role in the its treatment. Galactosidase (gal) is an enzyme that is
overexpressed in primary ovarian cancer and can be used as a
valuable biomarker for ovarian cancer. To this end, Wang et al.
(2017) have designed a novel two-photon fluorescent probe 40

Fig. 35 (a) The structure of sensor 39, (b) the fluorescence spectral of
Fig. 33 Design and synthesis of probe 37 for the detection of lysosomal probe 39 before and after the addition of MAO-A with emission color
H2Sn. changes, (c) the structure of sensor A.

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(OLED), fluorescent sensing, solar photovoltaic cells, clinical

medicine, and other fields due to their structural changes, which
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are cheap and easy to modify. New high-efficiency organic light-

emitting materials and other materials are of great significance
for enriching the material system and for broadening their
application. As one of the most versatile groups, naphthalimide
has been used in many fields122–125 as this group has excellent
electron affinity, and its aromatic ring and N position can be
modified by a simple and low-cost synthetic route for various
multifunctional functional groups. Therefore, the development
and design of materials based on naphthalimide also have
Fig. 36 Proposed sensing mechanism of 40 for b-gal. extraordinary significance.126–129

4.1 Sensing gel

for monitoring endogenous gal in vivo lysozymes (Fig. 36).113 As a kind of soft material, gel has viscoelastic properties and
The probe uses 1,8-naphthalimide fluorophore as the typical can be shaped. It is widely used in skin care and medical
fluorescent reporter, morpholine group as the lysosomal targeting treatment. Therefore, designing new gels has a very important
group, and the gal cleavage unit as the enzyme activity trigger. value in today’s society.
Under the action of gal, the probe cleaves the glycosidic bond and Wei et al. (2017) used N-(pyridine-4-acyl)-naphthalimide
the fluorescence obviously changes from blue to green. The LOD derivative as a novel gel agent 49,130 which was assembled
was 4  10 5 U mL 1. under the action of n-valeric acid by p–p stacking and electro-
SNAP-tag is one of the most popular gene-encoded protein static interaction assembled into the supramolecular gel
tags that can be labelled with fluorescent molecules to display (49-Gel). Naphthalimide was used as a fluorescent signal group
the protein of interest in living cells. Fluorescent probes remain while pyridine was used as a binding site; the gel agent can be
dark before labelling with protein tags, thus significantly used for the highly sensitive detection of multiple substrates
improving the signal-to-noise ratio of the image protein with- such as I , Fe3+, Hg2+, and L-ser (Fig. 38).
out the need for washing steps. However, compared with non- Aggregation-induced emission (AIE) was reported by
fluorine-derived probes, most reported SNAP-tag fluorescent Tang et al. in 2001.131 Compared with traditional aggregation-
probes have lower or milder labelling rates. Xu et al. (2017) caused quenching (ACQ), AIE molecular aggregates show stronger
reported a 4-aminonaphthylamide fluorescent probe 41 for emission than single molecules.132 After nearly 20 years of
SNAP-tag, which has a fast recording labeling rate among development, AIE research has made great achievements
fluorescent probes (Fig. 37).114 Simultaneously, confocal ima- in the materials area, mechanics research, and high-tech
ging was carried out at different time points. The probe can applications.133–135 Therefore, designing a material with
image proteins in the mitochondria and the nuclei of live cells aggregation-induced enhancement effect can not only expand
without a washing step. In addition, there are some other the AIEgens but also provide a better basis for research in the
chemical sensors that can detect molecules; see Table 1 for field of medicine.136 Pillar[n]arene, as the main new generation
details. macrocycle, were first reported by Ogoshi in 2008.137 Pillar[n]-
arene exhibits various supramolecular assembly driving forces
including C–H


p, p–p, cation–p, ‘‘exo-wall p–p’’, and hydro-
4. Material applications phobic/hydrophilic, providing a novel development platform for
ultra-sensitive reaction materials.138 In addition, pillar[n]arene
In recent years, organic light-emitting materials and soft materials could be used as a new type of AIEgens as well.139 Therefore,
have been widely modified in organic light-emitting diodes it is necessary to develop AIE performance research based on
pillar[n]arene.
In 2018, Wei et al. successfully developed a novel and highly
efficient sensor 50.140 Naphthalimide was introduced into
the pillar[5]arene to form a supramolecular organic gel 50-G
in cyclohexanol, using cation–p and exo-wall p–p interactive
competition to obtain a hypersensitive method (Fig. 39).
Interestingly, 50-G showed hypersensitivity towards Fe3+ and
H2PO4 . In addition, 50-G has good practical potential for ion
detection separation, fluorescent display materials, and ultra-
sensitive logic gates. More importantly, this novel cation–p and
exo-wall p–p competition method for ultrasensitive reactions
provides a novel and simple method for manufacturing intel-
Fig. 37 Proposed sensing mechanism of 41 for SANP-tag. ligent response supramolecular materials.

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Table 1 Other reported chemical sensors for detecting molecules

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Fig. 38 The structure of gel agent 49 and fluorescence responses of the

ionic supramolecular gels in the presence of various anions, cations, and
amino acids.

Fig. 39 Proposed assembly and ultrasensitive-response mechanisms of

Hereafter, another naphthalimide-functionalized pillar[5]arene 50-G with Fe3+ and H2PO4 .
51 was synthesized, which with the previously reported compound
22 through the ‘‘exo-wall’’ p–p and p–p stacking interactions
assembled the AIE p-gels in DMSO solution (Fig. 40).141 The potassium-carboxylate coordination and p–p interactions as the
assembled gel could detect AsO2 in a highly sensitive way most substantial intermolecular forces.142 The gel is reversible
through the competition between lone pair–p and ‘‘exo-wall’’ under thermal, mechanical, or chemical stimulation.
p–p interactions; the lowest detection limit was 1.7  10 9 M. In 2019, Wei et al. successfully designed and constructed a
In addition, the xerogel powder of 51-G could also efficiently supramolecular polymer network gel 53-SPN (Fig. 42).143 Inter-
remove AsO2 from water. This work provides an ultrasensitive estingly, 53-SPN has detection and separation capabilities for
method for the detection and removal of AsO2 in water. broad-spectrum pollutants such as heavy metal ions, anions,
Gunnlaugsson et al. (2017) reported the synthesis of a new oxalates, various organic dyes, organic pollutants, and volatile
hetero-biligand N-(4-pyridyl)-4-(4-carboxyphenoxy)-1,8-naphthal- organic compounds. The LODs of the 53-SPN gel for cations
imide 52 in the presence of K+ ion (Fig. 41); a powerful photo- and anions are range in 10 8–10 9 M, and the separation rate
luminescent hydrogel could be formed using 52 through of heavy metal ions, oxidized metal acid salts, various organic

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Fig. 40 The possible mechanisms regarding the assembly of 51-G and

the ultrasensitive sensing of AsO2 .
Fig. 43 (a) The structure of gelator 54 and guest-TA, (b) the gel–sol
transitions of the supramolecular polymer gel 54-G triggered by different
stimuli.

multi-responsiveness to external stimuli, such as heating–

cooling and pH. More importantly, the 54-G xerogel has
separation properties for Fe3+, methyl orange, methylene blue,
and Sudan I dyes. The separation rate of the 54-G xerogel for
Fe3+ ions and organic dyes can reach 99.8%.

4.2 Fluorescent photochromic materials

Fig. 41 (a) The structure of gelator 52, (b) manipulation of the gel with Photochromic material refers to a type of material that can
tweezers and the transparency of a gel monolith.
change the color after being excited by a light source.145 This
type of material mainly includes spirogyras, diarylethene, and
azobenzene. Because of their excellent functions in stealth,
camouflage, anti-counterfeiting, and fluorescent indication,
photoluminescent and color-changing fibers have been widely
used in aerospace, military equipment, special process moni-
toring, product anti-counterfeiting identification, and other
fields. In addition, temperature discoloration and electrolumi-
nescent materials have gradually become the focus of research
in the material world.146–149
Song et al. (2017) designed and synthesized a new type of
‘‘push–pull’’ diarylethylethylene molecule 55, which consists of
an electron-withdrawing ethylene bridge (1,8-naphthalene
anhydride) and two medium electron-donating side chains
(2,5-dimethylthiophene) (Fig. 44).150 The study found that the
molecule has a reversible fluorescence switching ability during
Fig. 42 The structure of gel-53 and guest-G, Photo showing the broad- photoisomerization. It exhibits a strong ICT characteristic
spectrum detection and adsorption separation properties for broad-
spectrum pollutants for (a) cations and anions, (b) VOCs, (c) various organic
dyes.

dyes, and organic pollutants can reach 99.8%. The high sensi-
tivity and broad-spectrum adsorption and separation perfor-
mance of 53-SPN are based on the multiple interaction sites
that we reasonably introduce. Therefore, this is a convenient
method for preparing supramolecular polymer network sponge
composite functional materials.
Soon after, they synthesized new guest molecules (TA) and
naphthalimide-functionalized pillar[5]arene host (54) to design
Fig. 44 (a) Chemical structure and photochromism of 55, (b) absorption
and construct a multifunctional sponge-like supramolecular spectra changes of 55 upon irradiation at 365 nm in cyclohexane solutions
polymer gel (Fig. 43).144 Interestingly, 54-G showed a spongy (5.0  10 5 M), (c) fluorescence spectra changes of 55 upon irradiation at
structure and strong AIE. In addition, 54-G also showed 365 nm in cyclohexane.

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between the naphthalene anhydride vinyl bridge and two

substituted thienyl groups, and the fluorescence maximum
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red-shift exceeds 150 nm. In addition, the experimental data

and theoretical calculations show that this is due to the inter-
molecular charge transfer between the electron-donating side
chain and the electron-withdrawing ethylene bridge, which
makes the fluorescence highly dependent on the solvent.
At the same time, it also provides potential for monitoring
the polarity of the microenvironment in chemical and biological
systems.
The absorption of moisture from the atmosphere by materials Fig. 46 (a) The chemical structure of 57A and 57B, (b) 57A and 57B at
with different hygroscopicity can greatly change their physical different temperatures, (c) the relative fluorescence emission peak inten-
sity of (c) 57A and 57B in THF/water mixtures with different water fractions.
and chemical properties; thus, there has been an interest
in the development and manufacture of various commodities.
In particular, hydrogen-chromic materials have achieved great AIE active imide derivatives 57A and 57B, and developed red
commercial success as sensors and applications in the paint thermally-activated delayed fluorescence (TADF) emitter with
industry. These materials must be stretchable, easy to process AIE characteristics (Fig. 46)152 due to the strong electron-
from their raw materials, show versatility at the point of use, and deficient 1,8-naphthalimide receptor. In addition, strong
be sufficiently sensitive to changes in water. Here, Olson et al. electron-rich 10-H-phenothiazine (Pz) or 9,9-dimethyl-9,10-
(2019) reported two fluorescent receptors 56A and 56B, which dihydroacridine (DMAC) was chosen as the donor groups,
undergo reversible fluorescent hydrogen color change in the and 2,6-dimethylphenyl acted as the p-bridge. Due to the steric
solid state to respond to the changes in the atmospheric relative hindrance, the p-bridge and two D–p–A derivatives adopt a
humidity (Fig. 45).151 The system consists of a 1,8-naphthalimide twisted conformation, which results in restricted movement
fluorophore, an amphiphilic pyridine acceptor and its bromide between solid molecules.
ion. As a water-sensitive acceptor, it can participate in the Soon after, Pu et al. developed six high solid phase emission
emission unit through excited state charge transfer. The dynamic 1,8-naphthyl compounds (Fig. 47) (58A–F).153 The study found
vapor absorption isotherm shows that when the raw material that among them, 58A and 58C showed mechanical fluores-
absorbs water at a rate of 3.8%, the emission of the raw material cence discoloration, the color change was between blue,
is red-shifted from blue to green by 27 nm. Processing the blue-green, or green emissions, and 58D and 58F showed
material into an ultra-light agro-absorbent aerogel with water- mechanical fluorescence discoloration characteristics, including
induced discoloration can significantly increase its sensitivity to fluorescent colours from yellow-green or yellow to yellow
water-induced discoloration. In solution, as the ionic strength or orange. In addition, these polymerization-induced green
increases and the solution freezes, the material exhibits AIEE luminescence or polymerization-induced yellow light-emitting
after precipitation from the aqueous solution. The average red phosphors also exhibit different mechanical fluorescence dis-
shift was about 109 nm. In all the cases, a robust reversible solid- coloration phenomena. In order to investigate the mechanical
state hydrogenation discoloration is achieved and the sensitivity colour change mechanism of these six mechanically-stimulated
of changes in relative humidity can be adjusted by material reactive luminogens, powder X-ray diffraction (XRD) and X-ray
handling after the synthesis. This work provides a good basis single crystal measurements were performed. The XRD analysis
for the subsequent synthetic development and material proces-
sing of compounds that exhibit AIE or AIEE in the solid state.
Based on the strong electron coupling of the 1,8-naphthal-
imide receptor (A), Chi et al. (2019) designed two D–p–A type

Fig. 45 (a) The chemical structure of 56A and 56B, (b) photographs of
fluorescent aerogels depicting the fluorescence hydrochromism of 56A
and 56B based aerogels before and after being exposed to 90% RH taken
under 365 nm irradiation, (c) the UV-vis absorption and fluorescence Fig. 47 (a) Molecular structures of compounds 58(A–F), (b) PL spectra of
emission spectra of 56A and 56B aqueous solutions. luminogen 58(A–F) at different conditions.

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shows that it has interesting mechanical fluorescence behaviour

because of the conversion between crystalline and amorphous
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states. At the same time, the results of X-ray single crystal analysis
suggest that the distorted molecular conformation and the
absence of strong intermolecular forces lead to loosening of
the packing motifs, and the change in molecular packing is
responsible for the observed mechanical fluorescence effect. This
provides a valuable reference for the design of high-contrast
mechanical fluorescent materials based on 1,8-naphthalimide.
Cheng et al. (2019) used pyrene as the donor and 1,8- Fig. 49 Molecular structures of 60, (b) emission spectra of 60 in glycerol/
naphthalimide as the acceptor; a chiral D–A enantiomer (59A–B) water (85/15, v/v) mixture (left) and ethanol (right) recorded from 233 K to
was synthesized as a circularly polarized electroluminescence 323 K.
(CP-EL) emitter (Fig. 48).154 This chiral emitter exhibits good
thermal stability in the solid state (Td = 389 1C, Tg = 112 1C),
high fluorescence quantum yields (46.4/42.4%), and CPL-active
materials. Notably, the non-doped CP-OLEDs based on 59A/B
emitters can emit high green brightness CP-EL with gel signals
of +2.15  10 3 and 2.23  10 3, respectively. This work
provides a new perspective CP-EL emitter for the design of rigid
chiral structures.
Xu et al. (2016) reported a novel fluorescent intelligent unit
based on bisnaphthalimide 60 (Fig. 49),155 in which two frag-
ments of naphthalimide are conjugated at the 4-position by
twisting the single bonds. Taking advantage of the character-
istics of the bis-naphthalimide planar structure, 60 can be used
as a dual-channel rotor, outputting shorter emissions in the Fig. 50 (a) Synthetic TADF compound of 61A–Q, (b) visual representation
twisted state and longer emissions in the planar state. Due to of 61-N at various temperatures.
the limitation of the intramolecular rotation effect, 60 shows
strong emission characteristics in a high viscosity environment.
The longer and shorter emission in the aggregate is due to the Hudson et al. (2020) designed and synthesized naphthalimide-
synergistic effect of RIR and intramolecular planarization. The based red emission TADF acrylic monomer 61 (Fig. 50).156 When
probe produces a logarithmic response to different ratios of copolymerized with the host material by Cu(0)-reversible inactiva-
glycerol/water system viscosity. In addition, a very interesting tion radical polymerization (Cu(0)-RDRP), the polymer appears as
viscosity-dependent temperature response was also explored in a orange to deep red TADF, and the quantum yield in solution and
the fluorescence signal. We believe that this kind of fluorescent solid is as high as 58% and 31%, respectively. Utilizing this dual
sensor can distinguish the temperature-induced viscosity emission characteristic, the naphthalimide-isopropylacrylamide
change more effectively than that in other cases. dopant copolymerization produces blue fluorescence, preparing
a red to blue temperature-responsive polymer. These polymers
exhibit red TADF at room temperature and blue fluorescence at
70 1C, with a high ratio of 32.4% K fluorescence thermal response.
This system is expected to play a role in bioimaging, drug delivery,
and temperature sensing, thus further expanding the application
range of red TADF materials.

4.3 Other aspects

In recent years, organic light-emitting diodes (OLEDs),157 light-
emitting diodes (LEDs),158 solar cells,159 etc., have made great
progress in flat panel displays, surface light sources, and energy
applications, and are also expected to become flexible devices
in terms of new-generation display technology and energy
storage.160–163
The construction of novel highly efficient OLED materials
with TADF is still a challenge in molecular designing. Lu et al.
Fig. 48 (a) Molecular structures of 59A and 59B, (b) cyclic voltammo-
(2018) reported a pair of novel TADF enantiomers ( )-(R,R)-62
grams of 59B in CH2Cl2 solution, (c) calculated spatial distributions of the and (+)-(S,S)-62 introduced chiral unit 1,8-naphthalimide-based
HOMO and LUMO energy densities of 59B. TADF skeleton (Fig. 51a).164 The enantiomer with TADF has

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Fig. 51 (a) Molecular structures of TADF enantiomers ( )-(R,R)-62 and

(+)-(S,S)-62, (b) the thermogravimetric thermogram and differential scan-
ning calorimetry trace of ( )-(R,R)-62, (c) cyclic voltammogram of
Fig. 53 (a) Molecular structures of 64, (b) AFM topography images of
( )-(R,R)-62 with ferrocene as the internal standard.
perovskite films 64 and surface charge mapping by Kelvin probe force
microscopy (KPFM) of sample 64.

high thermal stability (Td = 405 1C), excellent electrochemical

performance, and obvious TADF properties with small singlet– the molecular structure modification on the performance of the
triplet energy gap (DEST = 0.07 eV). The enantiomer also shows perovskite solar cell was studied. The photoluminescence
stable optical rotation with mirror image circular dichroism quenching experiment confirmed the effectiveness of the per-
(CD) and circularly polarized luminescence (CPL) activity. ovskite film containing the 64 layers. It was found that
In addition, by using the enantiomers as emitters, the the lowest unoccupied molecular orbital (LUMO) energy was
OLEDs exhibit orange-red emission centered at 592 nm, with 3.75 eV. The power conversion efficiency (PCE) of the device
maximum external quantum efficiency (EQE) values of 12.4% made with 64 was 10.79%, the photocurrent density ( Jsc) was
and 12.3%, respectively. 20.23 mA cm 2, the open circuit voltage (Voc) was 1.078 V, and
Zivic et al. (2019) reported four N-[2-(dimethylamino)ethyl]- the fill factor (FF) was 0.497. In addition, using 64 as an ETM
modified 1,8-naphthalimide derivatives (63A–D),165 which con- can obtain induced pluripotent stem cells with an inverted
tain different substituents (bromine, primary amine, secondary structure.
amines, and tertiary amines) to modify the naphthalimide Lalevee et al. (2015) reported 7 naphthalimide-based deriva-
framework. These novel frameworks could be as a single- tives (65-A/G) for the multifunctional development of near-
component free radical light or a multi-component free radical ultraviolet/visible LED, 3D printing, and water-soluble priming
or cationic photopolymerization initiator system under a vari- system (Fig. 54).167 By linking nitro-, iodo-, or bromo-substituted
ety of LED lamp irradiation (Fig. 52). Using 63-C (containing compounds to naphthalimide, (65-A, 65-C, or 65-E) did not show
secondary amine substituents) or 63-D (containing tertiary good light absorption properties, resulting in low initiation ability.
amine substituents) alone can initiate the free radical polymeri- The substituent at the nitrogen position of the naphthalimide
zation of acrylate at 405 nm under the LED, while using 63-A structure (65-G) ensures red-shift absorption but reduces the
(containing bromine substituents) or 63-B (containing mono- solubility. It is worth noting that 65-B/Iod, 65-D/Iod, and
amine substituents) does not work. This shows that the amine 65-F/Iod exhibit excellent efficiency for the cationic polymeriza-
substituent (whether it is a monoamine, diamine, or tertiary tion of epoxy compounds (50% conversion rate) when they are
amine) can significantly improve the photoinitiation ability of irradiated with 405, 455, or 470 nm LED or halogen lamps.
the polymerization reaction. However, it is worth noting that 65-B/Iod, 65-D/Iod, and
Subsequently, Nogueira et al. designed a new fullerene 65-F/Iod show excellent efficiency (50% conversion rate) for
functional naphthalimide 64 (Fig. 53).166 By using 1,8-naphthal-
imide as a substituent, an inverted perovskite solar cell was
prepared as the electron transport material (ETM). The effect of

Fig. 52 Chemical structures of the investigated photoinitiators 63(A–D), Fig. 54 Chemical structures of the studied naphthalimide derivatives
(b) UV-vis absorption spectra of 63(A–D) in acetonitrile. (65-A/G).

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Fig. 56 (a) Chemical structures of compounds 67 and GBP, (b) fluores-

cence images of live HeLa cells.
Fig. 55 (a) Chemical structures of 66-A/D, (b) cyclic voltammetric curves
of 66-A/D, (c) energy level diagrams of PCDTBT-C12, 66-A/D, and
PC71BM.
probes to accurately distinguish cancer cells from normal cells
is of great significance in clinical diagnosis and prognosis.
the cationic polymerization of epoxy compounds. 65-B/Iod/NVK In 2017, Wei et al. synthesized a novel naphthalimide-
or 65-B/MDEA/chlorotriazine three-component system under functionalized pillar[5]arene derivative 67 as a host; at the
405 nm light irradiation acrylate radical polymerization effect same time, they synthesized a guest (GBP) and assembled a
had more efficiency than the cq system or the BAPO system. supramolecular polymer through host and guest assembly
PDSs based on 65 also allow 3D objects to be manufactured (Fig. 56).175 Then, by reasonably introducing the electron donor
using 3D printers. effect of I into the functional pillar[5]arene-based supra-
Bo et al. (2016) designed and synthesized four small mole- molecular system, different redox properties were produced,
cule receptors (66-A/D) composed of a central benzene nucleus, which enabled the supramolecular polymer to reduce and
two thiophene bridges, and two 1,8-naphthalimide end groups detect CN , Hg2+, and cysteine. The amino acid exhibits a
(Fig. 55).168 By attaching different substituents to the central highly efficient fluorescent phase and the constructed supra-
benzene ring, the dihedral angle between the two end groups of molecular polymer network was successfully used for cell
66-A/D gradually increased, resulting in a gradually reduced imaging. This is a novel, simple, and efficient preparation
planarity. 66-A had a planar chemical structure and could form method in fluorescence imaging.
hydrogen bonds so as to form a film. 66-A/D had a high-energy The ortho-dithiol-containing proteins (VDPs) mainly main-
level LUMO, which matches the wide-band gap (WBG) polymer tain the structure and function of proteins through the conver-
donor that usually has a high-energy level LUMO. Among OSCs, sion of dithiol and disulfide bonds. The content of VDPs also
devices based on 66-A and WBG donor PCDTBT-C12 have reflects the redox state of the organism. In order to accurately
higher electron mobility, superior film morphology, and better and conveniently detect VDPs, Fang et al. (2020) developed a
photoelectric performance. After optimization, the PCE of the single arsenide photoprobe based on the ICT mechanism 68
66-A-based devices was 2.78% and Voc was 1.04 V, which is one (Fig. 57).176 Naphthalimide was selected as the fluorophore and
of the devices with the highest PCE when Voc is greater than 1 V. connected to the acceptor moiety (cyclodithioalkane) through the
The result of this study is that the development of small carbamate segment. In the presence of VDPs, the probe showed a
molecule receptor-based planarity has a significant effect on strong green fluorescent signal generated by the cleavage of
the performance of non-fullerene OSCs. cyclodithioarsane and subsequent intramolecular cyclization,
thereby releasing the fluorophore. In addition, the probe has high
selectivity for VDPs compared to other protein thiols and low
5. Bioimaging molecular weight thiols. The good properties of NEP make it easy
to detect VDPs in living cells and in vivo. In addition, it was the
Bioimaging plays an important role in the accurate identifi- first time that VDPs of Parkinson’s disease were significantly
cation of tumor cells and normal cells, and in the clinical decreased, which indicates that regulating VDPs levels has
diagnosis and prognosis of various types of cancer. Therefore, potential value for the treatment of Parkinson’s disease.
the development of biological imaging is the most direct and Mitochondria are double membrane-associated subcellular
effective detection method.169 In recent years, the visualization organelles and the center of eukaryotic cells, which regulate
of important active molecules in organisms has been a research various biochemical processes. For example, 95% oxygen consump-
hot topic in the field of analysis.170,171 Compared with other tion stimulates the cells to produce the major parts of adenosine
detection technologies, small-molecule fluorescent probes can triphosphate, generate most of the cell reactive oxygen species, and
monitor biomolecules in complex biological systems due to initiate apoptosis. Therefore, the design of mitochondrial targeting
their high sensitivity and high specificity focus as the advan- molecules to report and manipulate mitochondrial functions has
tages of imaging.172–174 Therefore, using small molecular aroused considerable interest.

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Fig. 59 (a) Molecular structures of 70-A/G, (b) confocal fluorescence

microscopy of S. pombe yeast cells incubated with fac-[Re(phen)-
(CO)3(70-A)]BF4 depicted in green.

Fig. 57 (a) Proposed sensing mechanism for the activation of 68 by VDPs,

(b) imaging VDPs in live cells. of nuclear imaging to ensure that the background signal was
minimized. The design of intrinsic fluorescent chelates has
very important application prospects in the fields of biology
Pope et al. (2020) synthesized 6 different 1,8-naphthalimide and bioimaging in the future.
coupled dimer amine ligands (69-A/F) (Fig. 58).177 The ligands The main ingredient of yeast is protein, which accounts for
have a series of different naphthalimide fluorophores and almost half of the dry one and has sufficient essential amino
colylamine chelating agents between the connecting units, acids, especially the low content of lysine in cereals. On the
which allows the overall lipophilicity to be adjusted. A series other hand, it contains a lot of niacin vitamin B1 and B2.
of corresponding Re(I) complexes were synthesized in the form Therefore, yeast could improve the nutritional value of fermented
of fac-[Re(CO)3(69-A/F)]BF4. The absorption and luminescence food. But yeast is a fermenting bacterium. If the dosage exceeds
properties of ligands and Re(I) complexes is mainly dependent the standard, it will cause excessive fermentation of the food and
on the intramolecular charge transfer properties of the sub- cause food deterioration, and promote the growth of bacteria.
stituted fluorophores whose usual absorption was about Meanwhile, if the body consumes too much yeast, it will cause
425 nm and 520 nm. Fluorescence confocal microscopy showed diarrhea and other diseases. In severe cases, it may also cause skin
that fac-[Re(CO)3(69-E)]+ is present in the mitochondria of and respiratory tract diseases. Subsequently, Pope et al. (2017)
MCF-7 cells. SPECT/CT imaging experiments on naive mice synthesized pyrrole-derived ligands to modify a series of naphtha-
show that fac-[99mTc(CO)3(69-E)]+ has high stability in vivo. Cell limide derivatives 70-A/G (Fig. 59).178 These ligands cooperated
bioimaging of the MCF-7 cell line shows good image quality. with Re(I) to form fac-[Re(phen)(CO)3(70-A/G)]BF4 mixed ligand
The preliminary in vivo evaluation of water-soluble 99mTc(I) species. This produces a fluorescent substance with adjustable
compounds showed rapid clearance, meeting the requirements emission. Some complexes were selected for cell imaging studies
with simply two of (70-A/70-G), which proved to be viable cell
imaging agents. The absorption of these complexes appears to be
regulated by the functional properties of naphthalimide, with the
most lipophilic variants showing the best cellular uptake.
Lysosomes are organelles that can break down biological
macromolecules such as proteins, nucleic acids, and poly-
saccharides, which have a single-layer membrane and various
shapes. It is a bubble-like structure of 0.025–0.8 microns and
contains many hydrolytic enzymes. All white blood cells
contain lysosomal particles, which can destroy invading micro-
organisms. However, there are some pathogenic bacteria (such
as leprosy bacillus and tuberculosis bacillus) that can tolerate
the action of lysosomal enzymes, and thus can survive in
macrophages. It is important that lysosomes play an irreplace-
able role in the pathological process. In addition, intracellular
pH is an important parameter for regulating many biological
Fig. 58 (a) Molecular structures of 69-A/F, (b) confocal fluorescence
microscopy images of MCF-7 cells incubated with fac-[Re(CO)3(69-E)]+
processes such as cell proliferation, apoptosis, enzyme activity,
(top left) and Mito Tracker deep red (left, middle) and overlay (right; overlap and tumor growth. Therefore, the design of cell fluorescence
coefficient = 0.66). imaging for the detection of lysosomes and pH is of great

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Fig. 60 (a) The proposed mechanism of 71 for sensing H+, (b) fluores-
cence microscopy images of living HeLa cells co-stained with 71 (5 mM)
Fig. 62 (a) Molecular structures of 74, (b) co-localization of 74 and Lyso-
and LysoSensors Green DND-189 (1 mM).
Tracker Red in A549 cells.

significance to cell life. In 2018, Zhao et al. synthesized a novel

ratiometric pH probe 71 (Fig. 60) based on FRET.179 Probe 71
uses the naphthalimide moiety as a donor and the rhodamine
moiety as the acceptor. At the same time, 4-(2-aminoethyl)-
morpholine was introduced, which is a lysolytic group. The
sensing mechanism is the integration of PET and FRET pro-
cesses, and the combined effect causes the strength of naphtha-
limide and rhodamine to increase at the same time as the pH
decreases. The probe has good selectivity among various metal
cations, amino acids, and ATP. In addition, the probe can also
selectively stain lysosomal pH changes in HeLa cells. Also, the
probe showed low cytotoxicity in living HeLa cells.
The activation of cancer cell apoptosis and understanding
its working mechanism play a critical role in formulating
Fig. 63 (a) Molecular structures of 75A–H, (b) CLSM images of HeLa cells
effective cancer treatment strategies. Here, Lin et al. (2020) incubated with probe 75-A.
reported a selenium-containing fluorescent apoptosis agent 72
(Fig. 61).180 MPSE realizes the tracking and imaging of the

Fig. 64 (a) Proposed mechanism of H2S release from probe 76 and HPLC
Fig. 61 (a) Molecular structures of 72 and 73, (b) co-localization real-time study of H2O2 induced HSD-B transformation, (b) confocal ratiometric
tracking of ROS production in living DU145 cells. fluorescence images on H9c2 cells.

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apoptosis process of cancer cells. In the presence of thioredoxin Over-expressed nitroreductase (NTR) is a common bio-
reductase (TrxR) in the mitochondria, a non-emitting com- marker of tumor hypoxia. Tang et al. (2020) designed and
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pound 73 is formed. This emission shutdown phenomenon synthesized a compound (74) of 1,8-naphthimide modified
allows the monitoring of the mitochondrial damage induced by with p-nitrobenzene, covalently attached to the side chain of
reactive oxygen species (ROS). As the dysfunctional mitochon- poly(fluorene-co-phenylene) (PFP) (Fig. 62).181 This compound
dria are cleared by the lysosome, 73 enters the lysosome and its can cause both FRET and PET to occur simultaneously. When
protonation leads to increased fluorescence. The results show NTR is present, the nitro group is reduced to an amino group,
that MPSE is very useful in elucidating the working mechanism causing the PET to be blocked. Therefore, the ratio is greatly
of theranostic-based optical apoptotic agents and it is hoped increased and the LOD was 19.7 ng mL 1. It is important that
that this mechanism will greatly promote the development of the fluorescence of the PFP backbone remains unchanged,
new cancer treatment methods. which allows it to be used as an internal reference. In addition,

Table 2 Other reported chemical sensors for cell imaging

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the ratio probe has high selectivity and low cytotoxicity, and can five years, which provides opportunities for promoting
realize NTR detection and hypoxia diagnosis in tumor cells. development in this field. In the past years, naphthalimide
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RNA is a product of cell metabolism and has a wide range of has become a powerful and highly adaptable platform.
functions, including protein synthesis, gene regulation, and We hope that this fluorophore has a bright future in the field
reaction catalysts. RNA mainly includes mRNA (mRNA), tRNA of fluorescence sensing. However, from the perspective of
(tRNA), and rRNA (rRNA). rRNA is the most abundant RNA. It is applications, there are several issues that need to be resolved:
produced in the nucleus and can be assembled with ribosomal (1) In the future, priority should be given to the development
proteins in all organisms to form ribosomes. However, these of fully biocompatible probes. This means that developing and
methods do not provide spatiotemporal information for three- designing water-soluble sensors is crucial. The above sensors
dimensional cells. Therefore, a method to display rRNA quickly basically exist in a large amount of organic solvents, which
and selectively in living cells is crucial. In 2019, Yi et al. should be solved.
developed a naphthalimide derivative probe 75 for the rapid (2) In terms of ion detection, most of the above reported
and selective detection of intracellular rRNA.182 Probe 75-A chemical sensors detect metal ions and toxic metal ions but few
showed a 32-fold increase in the fluorescence in response to of them detect alkali metals. For example, sodium ions have an
rRNA binding and showed good selectivity for rRNA relative to irreplaceable role in the adjustment of the osmotic pressure
DNA and other nucleic acid phosphate buffers at pH 7.2. More balance of human fluids. Therefore, it is necessary to develop a
importantly, 75-A has excellent nucleolus permeability and can sensor for alkali metal ion detection. In addition, in anion
be occupied by 4 different cell lines within 1 min. This is detection, the anion detection range should be expanded.
currently the fastest nucleolar dye (Fig. 63b). At the same time, (3) For applications in in vivo bioimaging, the naphthal-
the magnified nucleolar confocal laser micro-image and RNase imide scaffold should be altered to allow excitation and
digestion test showed that a pair of rRNA is highly selective, emission in the red and near infrared (NIR).
even for intracellular imaging. In addition, as a live cell probe, (4) Organic electroluminescence, temperament discolora-
due to the advantages of 75-A, including its water solubility, tion, and other materials play important roles in improving
excellent selectivity, remarkable photostability, biocompatibility, the photoelectric performance of light-emitting diodes. Organic
and peculiar cell permeability, we expect that this probe may small molecule emitters based on naphthalimide have attracted
provide an alternative tool for commercial rRNA staining. more and more attention due to their unique characteristics of
In 2020, He et al. introduced a new type of proportional electron extraction, rigid structure, and high fluorescence quan-
fluorescent H2S donor 76 (Fig. 64).183 The probe has the tum yield. In recent years, aromatic imide/amide semiconductors
following advantages: scavenges reactive oxygen species (more have been developed rapidly but there are few reports on their
specifically H2O2) while simultaneously generating H2S; application in OLEDs. Therefore, designing high-performance
provides ratio fluorescence that visualizes and quantifies H2S luminescent materials is a very meaningful study.163
release; specifically targets the mitochondria. This work pro- (5) In recent years, with the rapid development of
vides a new effective strategy for the design of fluorescent H2S Aggregation-induced emission (AIE) and Aggregation-induced
donors and provides strong evidence for the protective effect of emission enhancement (AIEE), the development of sensors with
cell models on myocardial ischemia-reperfusion injury. There AIE effect has become a research hot topic. Similarly, molecules
are other fluorescent chemosensors used in cell imaging and that develop naphthalimide and its derivatives in AIE and AIEE
medicine that have not been introduced one by one; see Table 2 chemiluminescence should be designed and studied.200
for details. Overall, we believe that there will be many fluorescent
chemical sensors based on naphthalimide in the near future,
and the structures and functions will be more novel and versatile.
6. Conclusion At the same time, we also hope that this review will promote
interest and new ideas in this emerging field of research.
1,8-Naphthalimide is a member of the family of classic dyes
and fluorophores. Due to its high fluorescence quantum yield
and easy modification property, especially the modifications of Conflicts of interest
different substituents (–NH2, –OH) at the 4-position, it shows
different fluorescence phenomena, which greatly expand its There are no conflicts to declare.
application. 1,8-Naphthalimide and its derivatives have been
widely used in chemical sensing, materials, biological imaging,
and other fields. Compared with other complex chemical Acknowledgements
molecules, it has the advantages of simplicity, high selectivity,
and high sensitivity, thus providing a broader research prospect This work was supported by the National Natural Science
for its application. Foundation of China (No. 21662031; 21661028; 21574104) and
This review summarizes the latest research progress in the Program for Chang jiang Scholars and Innovative Research
the field of ion detection, molecular recognition, material Team in University of Ministry of Education of China
application, biological imaging, and other aspects in the past (No. IRT15R56).

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