International Journal of Biological Macromolecules 130 (2019) 928–937

Contents lists available at ScienceDirect

International Journal of Biological Macromolecules

journal homepage: http://www.elsevier.com/locate/ijbiomac

Synthesis, characterization and application of copper oxide chitosan

nanocomposite for green regioselective synthesis of [1,2,3]triazoles
Khaled D. Khalil a,c, Sayed M. Riyadh b,c, Sobhi M. Gomha c,d, Imran Ali b,e,⁎
a
Department of Chemistry, Faculty of Science, Taibah University, Yanbu 46423, Saudi Arabia
b
Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia
c
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
d
Department of Chemistry, Faculty of Science, Islamic University in Almadinah Almonawara, Almadinah Almonawara, 42351, Saudi Arabia
e
Department of Chemistry, Jamia Millia Islamia, (Central University), New Delhi, India

a r t i c l e i n f o a b s t r a c t

Article history: Chitosan copper (II) oxide nanocomposite was synthesized, characterized and used to synthesize [1,2,3]
Received 1 February 2019 triazoles. Nanocomposite was characterized by using FTIR, XRD, FESEM, and EDS techniques, which
Received in revised form 17 February 2019 reflected rough morphology. The powerful catalytic activity of hybrid nanocomposite was utilized to syn-
Accepted 2 March 2019
thesize chalcones (3a-p) in relatively high yields (82%–98%) and multicomponent regio-selective cycload-
Available online 4 March 2019
dition of chalones, aryl halides (4), and sodium azide to afford the expected N-2-aryl[1,2,3]triazoles (5a-h)
Keywords:
(80%–95% yield) rather than N-1-aryl[1,2,3]-triazoles (6a-h). The performance of nanomaterial was opti-
Copper oxide chitosan nanocomposite mized by several variables. The capability of the nanocomposite was compared with previous work and
Characterization the nanocomposite was found more efficient, economic and reproducible. The hybrid nanocomposite
Green synthesis of [1,2,3]triazoles could be easily isolated form the reaction mixture and recycled four times without any significant loss of
Cycloaddition its catalytic activity. The reported catalyst is an inexpensive for good yields of the triazoles and may be
used at industrial production for the reported compounds.
© 2019 Published by Elsevier B.V.

1. Introduction synthesis [16,17]. On the other hand, bio-based materials when used
in the metal oxide nanoparticles synthetic method; a greener and cost
The campaign for green syntheses of biologically interesting het- effective catalysis is invoked. The nanoparticles of CuO stabilized with
erocycles was started shortly after the USA pollution prevention act biopolymers certainly can bring about green catalysis of organic trans-
(PPA) in 1990 [1]. High yield green chemistry reactions; which formations e.g. oxidation and cycloaddition reactions [18–21]. There-
used bio-based materials and one-pot syntheses; are intensively fore, the efforts were made to synthesize and characterize copper (II)
studied owing to the fact that these reactions are effectively time oxide chitosan nanocomposite material for the economic and maximum
saving and eco-friendly [2–8]. If these reactions could be conducted yields of a variety of N-2-aryl[1,2,3]triazole derivatives; as these mole-
in the absence of toxic catalysts and undesired solvents, an added cules are excellent UV/blue-light-emitting fluorophores and biologically
green value is achieved; as it is well established that the use of the important precursors [22]. The results of these findings are discussed
solvents is one of the major pollutants in fine chemicals industries herein.
[9–16].
Nanomaterials are gaining importance in various fields of science 2. Experimental section
and technology including catalysts. Many nanocatalysts have been
used in a wide range of reactions and industrial application. The use of 2.1. Materials and methods
nanomaterials has increased the yields dramatically with saving lot
amount of energy and man power and, hence, green approach. In this Sodium metal, copper acetate and chitosan of medium molecular
series, chitosan and its modified hybrid materials have been used as ef- weight (with 90% deacetylation) were purchased from Sigma Aldrich
ficient, heterogeneous, and recyclable basic catalysts for heterocyclic Co. Ltd., USA. Triple distilled water was used in all solution preparations.
The melting points were recorded with Gallenkamp apparatus and un-
corrected. The Fourier Transform Infrared (FTIR) spectra were recorded
⁎ Corresponding author at: Department of Chemistry, Faculty of Science, Taibah
in KBr pellets with a JASCO FT-IR-6300, system at a resolution of 4 cm−1
University, Al-Madinah Al-Munawarah 30002, Saudi Arabia. ranging 400–4000 cm−1. Field emission scanning microscopy (FESEM)
E-mail addresses: drimran.chiral@gmail.com, drimran_ali@yahoo.com (I. Ali). was carried out using a model Leo (Zeiss) Remotely Operationable

https://doi.org/10.1016/j.ijbiomac.2019.03.019
0141-8130/© 2019 Published by Elsevier B.V.
 K.D. Khalil et al. / International Journal of Biological Macromolecules 130 (2019) 928–937 929

wise till the color of solution changes from brick red to black with
continuous stirring. The mixture was placed in the microwave reflux
system for 10 min at 20% power under ambient air for 10 min while
the black powder was obtained. After cooling to room temperature,
the precipitate was separated by centrifugation and then washed ex-
tensively with distilled water, absolute ethanol, and finally with ace-
tone and dried in air at room temperature. The final products were
collected for characterizations.

2.3. Application of chitosan CuO as catalyst in the synthesis of chalcones

Scheme 1. Preparation of chitosan-based CuO nanocomposites under microwave

2.3.1. Method A
irradiation.
This method was adopted from the earlier ones [23–31]: A mixture
of arylethanone 1 (10.0 mmol) and aromatic aldehyde 2 (10.0 mmol)
in 30 mL absolute ethanol was mixed with 15 mL KOH solution (40%).
The reaction mixture was stirred for 3 h at room temperature and
Variable Pressure Field Emission SEM. Powder samples used in the mea- kept in a refrigerator for overnight till becomes quite thick. Then it
surements were made by compression of the polymer and then coating was diluted with ice-cold distilled water (40 mL), filtered, washed
with gold. Single crystal X-ray crystallographic analysis was performed well with cold water, dried in air and recrystallized from ethanol to
by using a RIGAKU RAPID II. The XRD measurements were performed at give chalcone products 3a-p.
room temperature on chitosan. Siemens diffractometer model D500
(Germany) operating in the reflection mode with Cu-Kα radiation
(35 kV, 30 mA) was used for analysis. 2.3.2. Method B
A mixture of arylethanone 1 (10.0 mmol) and aromatic aldehyde 2
(10.0 mmol) in 30 mL absolute ethanol was mixed with 10% wt Cs-
2.2. Preparation of chitosan based CuO nanocomposites CuO. The reaction mixture was refluxed for 3 h at 100 °C. The mixture
was filtered on hot to remove Cs-CuO catalyst and kept in a refrigerator
In 100 mL capacity round flask, 10 mL of 0.1 M Cu(CH3COO)2 so- for overnight till becomes quite thick. Then it was diluted with ice-cold
lution was added to 0.5 g chitosan (medium molecular weight grade) distilled water (40 mL), filtered, washed well with cold water, dried in
with continuous stirring for 20 min. Then 25 mL ethanolic solution air and recrystallized from ethanol to give the authenticated chalcone
containing sodium ethoxide was added to the stock solution portion products 3a-p.

Scheme 2. The representation of the preparation of the chitosan nano-material (a): 2D and (b): 3D.
930 K.D. Khalil et al. / International Journal of Biological Macromolecules 130 (2019) 928–937

2.4. Application of chitosan CuO (Cs-CuO) nanocubes as catalyst in azide were refluxed in dimethylformamide (DMF) at 80 °C in presence of 1
chalcone cycloadditions equivalent of Cs-CuO nanocomposite film for 24 h. Then, arylfluoride
4 (10 mmol) was added to the reaction mixture and the reaction
2.4.1. Method A continued for more 6 h. The solid product was filtered off and recrystal-
This method was adopted from the earlier ones [18,32,33]: An equi- lized from appropriate solvent to give expected N-2-aryl[1,2,3]-triazoles
molar quantities of chalcone 3, and sodium azide (10.0 mmol of each) 5a-h.

Fig. 1. FTIR of (a) chitosan and (b) Chitosan-CuO nanocomposites.

 K.D. Khalil et al. / International Journal of Biological Macromolecules 130 (2019) 928–937 931

Fig. 2. XRD of (A) chitosan, (B) chitosan-CuO, (C) CuO-Glass.

2.4.2. Method B (DMF) in presence of 10%wt of Cs-CuO nanocomposite film for 4 h (the
An equimolar quantities of chalcone 3, arylfluoride 4, and sodium reaction time was determined by following up the reaction with TLC at
azide (10.0 mmol of each) were refluxed in boiling dimethylformamide different time intervals). The solid product (so formed) was filtered

Fig. 3. FESEM of (a): chitosan and (b): chitosan-CuO nanocomposites.

932 K.D. Khalil et al. / International Journal of Biological Macromolecules 130 (2019) 928–937

Fig. 4. EDS of (A): chitosan and (B): chitosan-CuO nanocomposites.

 K.D. Khalil et al. / International Journal of Biological Macromolecules 130 (2019) 928–937 933

Table 1
Percentage yields of chalcones 3a-p using: (A) KOH; (B) Cs-CuO nanocomposite.

Ar Ar′ Structure of product % yield M.P. °C

A [ref.] B

3a C6H5 C6H5 80 [31] 92 56–57

3b 2-Furyl C6H5 94 [23] 98 80–81

3c 2-Thienyl C6H5 91 [24] 93 78–79

3d 2-Pyridyl C6H5 79 [23] 86 70–71

3e C6H5 4-ClC6H4 80 [25] 90 113–114

3f 2-Furyl 4-ClC6H4 80 [26] 89 133–134

3g 2-Thienyl 4-ClC6H4 90 [27] 95 118–119

3h 2-Pyridyl 4-ClC6H4 74 [23] 85 102–103

3i C6H5 4-CH3OC6H4 70 [28] 82 75–77

3j 2-Furyl 4-CH3OC6H4 73 [23] 84 73–74

3k 2-Thienyl 4-CH3OC6H4 98 [23] 96 102–103

3l 2-Pyridyl 4-CH3OC6H4 92 [23] 95 122–123

3m C6H5 4-NO2C6H4 80 [28] 84 164–165

3n 2-Furyl 4-NO2C6H4 87 [29] 90 148–150

3o 2-Thienyl 4-NO2C6H4 95 [30] 95 224–225

3p 2-Pyridyl 4-NO2C6H4 76 [23] 89 155–156

Scheme 3. Synthesis of chalcones by using KOH or Cs-CuO nanocomposite catalyst.

934 K.D. Khalil et al. / International Journal of Biological Macromolecules 130 (2019) 928–937

off and recrystallized from appropriate solvent to give authenti- Table 2

cated N-2-aryl-[1,2,3]triazoles 5a-h. The product structure was Recyclability of the Cs-CuO nanocomposite as basic catalyst.

confirmed via comparison of TLC and m.p. with to the reported State of catalyst Fresh catalyst Recycled catalyst
analogues. (1) (2) (3) (4)

Product 3a (% yield) 92 92 91 91 90
3. Result and discussion

3.1. Preparation of chitosan based CuO nanocomposites

two normal peaks i.e. one as a strong broad reflection at 2θ (20–21°)
CuO nanocomposites were synthesized by co-precipitation method and another as very small reflection at 2θ (36°), all of which are charac-
using chitosan as biostabilizers [34]. Although the preparation of the teristic of the polymers hydrated crystalline structure [41]. On the other
nano-crystalline transition metal oxides under microwave is considered hand, the interaction of chitosan with CuO (C) resulted in two charac-
as a promising and efficient method yet only few examples have been re- teristic peaks at 35.5 and 38.5 (Fig. 2B) that are the same peaks of
ported in the literature [35–38]. Herein, the applied method is based on pure glass supported CuO which indicated a clear evidence to the inter-
the formation of metal oxide by hydrolysis of metal salts under micro- action between chitosan backbone and CuO molecules.
wave irradiation (Scheme 1). The probable mechanism for such micro-
wave assisted hydrolysis has been reported by Wang et al. [34] as follows: 3.2.3. FESEM and morphological changes
A comparison of the surface morphology of unmodified chitosan and
The 2D and 3D representation of the preparation of the chitosan chitosan-CuO nanocomposites is shown below (Fig. 3). In Fig. 3a, the
nano-material is shown in Scheme 2 below. chitosan showed a fibrous surface while in the chitosan-CuO nanocom-
posites 3b indicated a great change in the surface by interaction with
CuO.
3.2. Characterization of chitosan-based CuO nanocomposites
3.2.4. EDS and estimation of copper
3.2.1. FTIR characterization In Fig. 4, a comparison of chitosan and chitosan-CuO nanocompos-
IR spectra of chitosan and chitosan-CuO nanocomposites are shown ites by EDS graphs showed the appearance of new signals that are re-
in Fig. 1. FTIR spectrum of pure Cs [39] (Fig. 1a) revealed a broad O\\H lated to the incorporated amount of cupper in the chitosan backbone.
stretching band at υ = 3419 cm−1, caused by intermolecular H- As shown in this figure, sample of 12.57 wt% Cu content was prepared
bonding, that is overlapped with an N\\H stretching band in the same and was then subjected to the characterization using different analytical
region. The characteristic bands for amide groups are found in this spec- tools.
trum at υ = 3446, 1653 and 1609 cm−1 while the bands at 2918, 2875,
1425 and 1380 cm−1 in the spectrum assigned to the C\\H bonds in Cs 3.3. Cs-CuO nanocomposites as basic heterogeneous catalyst in chalcone
chain. In Fig. 1b, splitting of the broad band above υ = 3000 cm−1 and synthesis
the appearance of two characteristic bands at 2151 and 2356 cm−1 is
considered as an evidence to the coordination between CuO and chito- Chalcones 3 with different aromatic moieties were prepared via
san backbone. Moreover, the effect of CuO interaction to the chitosan treatment of arylethanone 1 with aromatic aldehydes 2 in the presence
backbone is clearly appeared by the dramatic change in the finger of KOH or Cs-CuO nanocomposite as basic catalyst, in a comparable
print region of chitosan. In addition, IR bands at υ = 669, 596, yields (Table 1 and Scheme 3).
498 cm−1 were attributed to the Cu\\O stretching vibration of the As shown in Table 1, Cs-CuO nanocomposite gave prevailed yields of
CuO monoclinic phase [40]. chalcones 3a-p when used as basic catalyst over KOH under the
employed conditions. Also, the cross-linking nature of the Cs-CuO hy-
3.2.2. X-ray diffraction (XRD) brid nanomaterial made it readily isolated by simple filtration and effec-
XRD patterns for chitosan and chitosan-CuO nanocomposites and tively reused again for more than five times without loss of its catalytic
pure CuO on glass are shown in Fig. 2. Original chitosan (A) showed activity. In order to estimate the appropriate catalyst loading, a model

Fig. 5. Optimization of Cs-CuO nanocomposite in chalcone synthesis.

 K.D. Khalil et al. / International Journal of Biological Macromolecules 130 (2019) 928–937 935

Scheme 4. Mechanism of Cs-CuO catalyzed synthesis of chalcones.

reaction of acetophenone (10 mmol) and benzaldehyde (10 mmol) was Cs-CuO, which is basic in nature, to give the enolate anion intermediate
carried out using 1, 5, 10, 15, and 20% wt. of catalyst under the same re- (A) that can attack the carbonyl group and afforded β-hydroxy ketone
action conditions. The catalyst loading 10% wt was found to be the opti- intermediate (B). Elimination of water from the latter intermediate
mal quantity (Fig. 5) where this percentage of catalyst afforded the (B) furnished the respective chalcone as the end product.
maximum yield (85%) in the minimum time (90 min). The recovered
catalyst was reused four time and the results showed that the nanocom- 3.4. Cs-CuO nanocomposite as an efficient catalyst for azide chalcone
posite can be efficiently reused as such without a significant loss in its cycloadditions
catalytic activity (Table 2).
The plausible mechanism of chalcone 3a-p synthesis using basic cat- In the past decade, many scientists have developed different syn-
alyst Cs-CuO nanocomposite is depicted in Scheme 4. The initial step is thetic approaches of azide chalcone cycloadditions [18,32,33,42–44].
proceeded by abstracting the acidic hydrogen from arylethanone 1 by Most of the literature have reported the formation of N-1-aryl[1,2,3]-

Scheme 5. Cs-CuO nano-cubes catalyzed synthesis of N-2-aryl-[1,2,3]-trizaoles.

936 K.D. Khalil et al. / International Journal of Biological Macromolecules 130 (2019) 928–937

Table 3 inexpensive with good yields of the products and may be used at indus-
Percentage yields of N-2-aryl-[1,2,3]t-rizaoles 5a-h using: (A): CuO; (B): Cs-CuO trial production of the reported compounds.
nanocomposite.

No. Ar Ar′ R1 R2 % yield M.P. °C

A [ref.] B
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