RSC Advances

PAPER

Design and development of a novel cellulose/g-

Fe2O3/Ag nanocomposite: a potential green
Cite this: RSC Adv., 2016, 6, 13657
catalyst and antibacterial agent†
Ali Maleki,* Hamed Movahed and Reza Paydar

A cellulose/g-Fe2O3/Ag nanocomposite is synthesized and used as a catalyst for the synthesis of

Received 14th October 2015
Accepted 25th January 2016
DOI: 10.1039/c5ra21350a
www.rsc.org/advances
trisubstituted imidazoles and a-aminonitriles. This catalytic protocol is simple, the reaction yield is very
high, and the reaction time is very short. The remarkable magnetic properties of the nanocomposite
permit easy separation of the catalyst from the reaction mixture without considerable loss of catalytic
activity. In addition, antibacterial properties of the nanocomposite are investigated. For this purpose, S.
aureus as the representative of Gram-positive bacteria and E. coli as the representative of Gram-negative
bacteria are evaluated. To study the morphology and characterization of the prepared nanocomposite,
X-ray diffraction patterns (XRD), energy-dispersive X-ray spectroscopy (EDX), field-emission scanning
electron microscopy (FE-SEM), vibrating sample magnetometry (VSM) and thermal gravimetric analysis/
differential thermal analysis (TGA/DTA) are obtained.

Ag NPs to polymer and biopolymer surfaces is a smart way to

Introduction
In the recent years, the amount of attention to nanoscience paid
by chemists, physicist, biologists and other elds scientists has
been increased due to its novel and unique applications in
various elds. Therefore, nanomaterials have attracted signi-
cant research interest in the chemical and pharmaceutical
elds, due to their size effect, high specic surface area and
unique structural properties.1,2
Biopolymers, especially cellulose and its derivatives, have
some unique properties, which make them attractive alterna-
tives for conventional organic or inorganic supports for diverse
applications. Cellulose ber, that is obtained from woody
annual plants and agricultural by-products, is the most abun-
dant natural material in the world. Cellulose has been widely
studied during the past decades, because it is a biodegradable
and biocompatible material and a renewable resource.3,4 In
addition, magnetic materials can be easily separated from the
reaction media by an external magnet.5 Having unique proper-
ties at the nanoscale and a wide range of applicability for
optical, catalytic, magnetic, electrical and antimicrobial devices,
Ag nanoparticles (NPs) have recently attracted much attention
among chemists and physicists.6,7 In particular, chemists using
polymers and especially biopolymers in their research have
been convinced that introducing metal nanoparticles such as
Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran
University of Science and Technology, Tehran 16846-13114, Iran. E-mail: maleki@
iust.ac.ir; Fax: +98-21-73021584; Tel: +98-21-77240540-50
† Electronic supplementary information (ESI) available.
10.1039/c5ra21350a
improve the properties and applicability of the polymers and
biopolymers, effectively.8,9
Nanoparticles which are based on silver have attracted much
attention to themselves due to their strong antimicrobial
activity toward many different bacteria, fungi, and viruses and
its relatively low toxicity to humans.10 Ag NPs, either in metal
form or in ionic form, exhibit considerable cytotoxicity towards
an extensive range of microorganisms. Hence, it has been used
as an antibacterial agent in various experimental works.11,12
A recent effort for the synthesis of a magnetic antibacterial
nanocomposite based on bacterial cellulose was reported by
Sureshkumar et al.13 However, they employed dopamine as
a coating on the bacterial cellulose as the reducing agent and
stabilizer for the preparation of the antibacterial Ag NPs, which
requires complicated preparation procedures, and involved
some problems such as high preparation cost and deterioration
of the magnetic properties. In addition, its application in
biomedicine is limited because dopamine is a neurotransmitter
in humans. Accordingly, combination of Ag NPs with magnetic
cellulose composite to achieve exceptional properties seems to
be essential. In connection with our previous works,14,15 herein,
we have immobilized Ag NPs to magnetized cellulose composite
(Scheme 1). Then, we have demonstrated that it is a green
nanocomposite to catalyze organic reaction such as the
synthesis of substituted imidazole derivatives under solvent-
free conditions in excellent yields. Moreover, antibacterial
activity of the prepared nanocomposite has been investigated
and identied.
See DOI:
In recent decades, the importance of imidazoles in pharmacy
and chemistry has drawn much interest to imidazoles due to

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RSC Advances
Scheme 1 Preparation of cellulose/g-Fe2O3/Ag nanocomposite.
their chemical and biochemical properties. Also, compounds
with imidazole ring system have many pharmacological prop-
erties and can play an important role in biochemical processes.
The heterocyclic compounds including 2,4,5-trisubstituted
Fig. 1 EDX analysis of cellulose/g-Fe2O3/Ag nanocomposite.
13658 | RSC Adv., 2016, 6, 13657–13665
Paper
Fig. 2 XRD patterns of cellulose/g-Fe2O3/Ag nanocomposite.
imidazoles possess versatile pharmaceutical actions such as
anti-inammatory agents, anti-bacterial, p38 MAP kinase
inhibitors, anti-tumor agents, glucagon receptor antagonists
and inhibitors of mammalian 15-LOX. Hence, several tech-
niques for the synthesis of imidazoles have been developed.16
Fig. 3 FE-SEM images of cellulose/g-Fe2O3/Ag nanocomposite.
This journal is © The Royal Society of Chemistry 2016
Paper RSC Advances

Results and discussion size distribution chart is obtained. According to this chart the
particle size distribution is narrow and the size of most of the
To study the morphology and characterization of cellulose/g- particles is about 15–20 nm (Fig. 4).
Fe2O3/Ag nanocomposite, energy-dispersive X-ray spectroscopy The magnetic property of the nanocomposite was charac-
(EDX) and X-ray diffraction patterns (XRD) were used. EDX and terized using a vibrating sample magnetometer (VSM) at room
XRD patterns shown in Fig. 1 and 2, result further certify the
formation of Ag and g-Fe2O3 nanoparticles in cellulose micro-
crystal. The peaks located at 2q ¼ 30.2, 35.6, 57.4, 63.0 are
related to Fe2O3, the peaks located at 2q ¼ 38.1, 44.2, 64.4, 77.4,
are related to Ag and also the peak presented at 2q around 20 is
related to cellulose. Identied peaks in XRD patterns were
assigned to the well-crystallized silver (JCPDS 04-0783) and
g-Fe2O3 (JCPDS 25-1402) nanoparticles. Elemental mapping of
EDX patterns show that elements Fe, Ag, O, and carbon (Au
existence in the nanocomposite is due to its implementation as
a coating for material conductivity) exist in the nanocomposite.
Field-emission scanning electron microscopy (FE-SEM)
images also, were used for showing nanostructured surface of
the nanocomposite (Fig. 3). According to these images, particle

Fig. 6 TGA/DTA analyses of cellulose/g-Fe2O3/Ag nanocomposite.

Fig. 4 Distribution diagram of particles size of cellulose/g-Fe2O3/Ag.

Table 1 Optimization of conditions in the reaction benzil 2, benzal-
dehyde 3 and NH4OAc under solvent-free conditions at 100  C

Loading Time Yielda

Entry Catalyst (mg) (min) (%)

1 Cellulose/g-Fe2O3/Ag — 120 Nil

2 Cellulose/g-Fe2O3/Ag 1 120 Trace
3 Cellulose/g-Fe2O3/Ag 5 60 50
4 Cellulose/g-Fe2O3/Ag 8 30 80
5 Cellulose/g-Fe2O3/Ag 10 20 82
6 Cellulose/g-Fe2O3/Ag 15 10 91
7 Cellulose/g-Fe2O3/Ag 20 10 91
8 Cellulose 15 60 Trace
9 Cellulose/g-Fe2O3 15 60 35
10 Cellulose/Ag 15 60 78
a
Isolated yield.
Fig. 5 VSM curve of cellulose/g-Fe2O3/Ag nanocomposite.

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Table 2 Synthesis of 2,4,5-trisubstituted-1H-imidazoles 4a–o using cellulose/g-Fe2O3/Ag nanocatalyst under solvent-free conditions

Time (min) Yielda (%) Mp ( C)

Entry Product Benzil Benzoin Benzil Benzoin Observed Literature

1 10 15 91 90 270–272 272–274 (ref. 17)

2 20 30 93 90 190–192 190–191 (ref. 18)

3 25 25 94 90 228–230 230–232 (ref. 19)

4 25 35 95 91 231–233 228–231 (ref. 17)

5 20 30 92 90 269–271 258–260 (ref. 18)

6 10 20 91 89 264–266 262–264 (ref. 17)

7 10 25 91 91 290–292 >300 (ref. 18)

8 35 40 90 86 200–203 210–212 (ref. 18)

9 25 30 91 92 255–257 255–277 (ref. 20)

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Table 2 (Contd. )

Time (min) Yielda (%) Mp ( C)

Entry Product Benzil Benzoin Benzil Benzoin Observed Literature

10 20 30 88 84 168–170 174–176 (ref. 20)

11 20 30 87 85 227–229 230–232 (ref. 20)

12 25 30 82 82 203–205 204–206 (ref. 20)

13 30 40 84 80 196–198 196–198 (ref. 20)

14 10 20 92 91 234–236 236–237 (ref. 21)

15 20 30 85 83 194–196 196–197 (ref. 21)

a
Isolated yield.

temperature (Fig. 5). The magnetic property of the cellulose/
g-Fe2O3 is 13.2 emu g1. The magnetic property of cellulose/
g-Fe2O3/Ag nanocomposite is about 6.4 emu g1. This dropping
in the magnetic potential is due to the addition of Ag NPs to the
cellulose/g-Fe2O3. The obtained nanocomposite has a good
magnetic potential and can be separated from the reaction
medium easily by a magnet.
Thermal gravimetric analysis/differential thermal analysis
(TGA/DTA) of the cellulose/g-Fe2O3/Ag nanocomposite is shown
in Fig. 6. A slight weight loss can be observed below 250–260  C
that is related to the decomposition of a tiny amount of cellu-
lose in the nanocomposite. Another weight loss is seen at 300–
320  C that is related to decomposition of other impurities.
Main weight loss is happened at 370–410  C that is for
decomposition of organic materials presented in the nano-
composite. This weight loss temperature in contrast with
cellulose weight loss temperature that is about 250–260  C has
been signicantly increased and as a result its thermal stability
has been improved.
To investigate the catalytic ability of cellulose/g-Fe2O3/Ag
nanocomposite, a pilot experiment was carried out from the
reaction of benzil 2, benzaldehyde 3 and ammonium acetate to
produce 2,4,5-triphenyl-1H-imidazole 4a. Aer several tests, we
realized that the optimized conditions for the reaction is using
0.015 g of cellulose/g-Fe2O3/Ag at 100  C under solvent-free
conditions in a reasonable and short reaction time

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Table 3 Synthesis of a-aminonitriles (8a–e) in the presence of a catalytic amount of cellulose/g-Fe2O3/Ag nanocomposite under solvent-free
conditions

Time Yield
Entry R1 R3 Product (min) (%)

1 4-Chlorophenyl Phenyl 8a 20 85
2 2-Chlorophenyl Phenyl 8b 25 86
3 Phenyl Phenyl 8c 25 82
4 4-Methoxyphenyl Phenyl 8d 35 83
5 4-Chlorophenyl 4-Methylphenyl 8e 40 80

(10 minutes) and high yield (91%) to produce 4a (Table 1,

entry 6). It is noteworthy that, considered product with such
efficiency could not be obtained under similar reaction condi-
tions, neither in the absence of any catalyst nor other catalysts
which have been used yet. The reaction was also done by
cellulose, cellulose/g-Fe2O3 and cellulose/Ag. The results
showed that their catalytic ability is not comparable with
cellulose/g-Fe2O3/Ag nanocomposite (Table 1, entries 8–10).
Subsequently, to investigate the efficiency and applicability
of this nanocomposite as a catalyst in the three-component
synthesis of 2,4,5-trisubstituted-1H-imidazoles 4a–o, the reac-
tion was extended to other substituted benzaldehydes 3 at 100

C under solvent-free conditions (Table 2). According to this
table, it is obvious that when benzoin 1 is used instead of benzil
2, the reaction time is longer. Also, it is obvious that the reaction
time of 3-nitrobenzaldehyde is the lowest; it can be attributed to
electron affinity of nitro group that is placed in meta-position of
benzaldehyde 3. Scheme 2 Proposed mechanism for the synthesis of substituted
The catalytic ability of the nanocomposite was also investi- imidazoles using cellulose/g-Fe2O3/Ag nanocatalyst.
gated in another important three-component reaction for the
synthesis of a-aminonitriles 8a–e (Table 3). The excellent results
demonstrated that it could have good activity to be employed as One of the advantages of this active, non-toxic, and envi-
a new nanocatalyst in further reactions. ronmentally benign heterogeneous catalyst is the ability to act
A proposed mechanism for the synthesis of 2,4,5-trisub- as a recyclable reaction medium. In multicomponent synthesis
stituted-1H-imidazoles 4a–o has been shown in Scheme 2. of substituted imidazoles, the cellulose/g-Fe2O3/Ag could be
According to the mechanism, ammonium acetate decom- adsorbed onto the magnetic stirring bar, when the stirring was
poses into ammonia and acetic acid, and this released stopped, recovered and reused several times in the subsequent
ammonia is a nitrogen source. It can be said that Ag and runs by using the same recovered catalyst without considerable
g-Fe2O3 groups presented in cellulose/g-Fe2O3/Ag nano- loss of catalytic activity (Fig. 7).
composite as Lewis acids are responsible for the activation of Results of antibacterial assays of nanomaterial and its
the carbonyl groups, so the rate of the imine producing is component are shown in Table 4. As could be seen, cellulose/
increased.22 g-Fe2O3/Ag showed the highest antibacterial activity comparing to
The imidazole synthesis reaction was also done under cellulose and g-Fe2O3. MIC values of this ample were 512 and
oxygen as well as inert atmosphere in the presence of cata- 1024 mg mL1 for assessed S. aureus and E. coli, respectively. On
lytic amount of cellulose/g-Fe2O3/Ag nanocomposite. The the other hand, visible growth of the two bacterial strains was
results showed that the reaction did not occur under inert inhibited completely by these concentrations of sample. The
conditions; but, it was progressed under oxygen. Accordingly, lowest concentration of cellulose/g-Fe2O3/Ag which could kill both
the designed catalyst had no oxidation property and the tested bacteria was 1024 mg mL1. Moreover, MIC value of cellu-
oxygen of air was responsible for the oxidation stage in the lose against S. aureus was 512 mg mL1; but, this sample could not
reaction. inhibit E. coli at concentration of 1024 mg mL1. g-Fe2O3 had no

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Fig. 7 Reusability of cellulose/g-Fe2O3/Ag for the synthesis of 4a.
Table 4 Results of antibacterial assays of nanomaterial and its
components
Experimental section
General
All the solvents, chemicals and reagents were purchased from
Merck, Fluka and Aldrich. Melting points were measured on an
Electrothermal 9100 apparatus and are uncorrected. IR spectra
were recorded on a Shimadzu IR-470 spectrometer by the
method of KBr pellet. 1H and 13C NMR spectra were recorded on
a Bruker DRX-500 Avance spectrometer at 500 and 125 MHz,
respectively. FE-SEM images were obtained on a Sigma Zeiss.
EDX spectra were recorded on Numerix DXP–X10P. XRD
measurements were carried out using a JEOL JDX–8030 (30 kV,
20 mA). TGA/DTA was measured by a STA504. Magnetic
susceptibility measurements were performed using a Lake
Shore VSM 7410. The products were identied by comparison of
their spectroscopic and analytical data with authentic samples.

S. aureus ATCC 25923 E. coli ATCC 25922 Synthesis of cellulose/g-Fe2O3/Ag nanocomposite

MIC MBC MIC MBC First, 1 g of PEG-2000 and 8.0 g of NaOH were added into 90 mL
Sample (mg mL1) (mg mL1) (mg mL1) (mg mL1) of ultrapure water to prepare the mixture aqueous solution of
PEG/NaOH. Then, 2 g of cellulose was added to the mixture and
Cellulose 512 >1024 >1024 >1024
swell for 3 h at room temperature. Then the suspension was
g-Fe2O3 >1024 >1024 >1024 >1024
Cellulose/g-Fe2O3/Ag 512 1024 1024 1024 cooled down to 15  C and held at that temperature overnight
Cexime 2 16 8 32 (12 h) until it became a solid frozen mass. The frozen solid was
then allowed to thaw out at room temperature under strong
stirring, and at the end a homogeneous cellulose solution was
obtained. FeCl3$6H2O and FeCl2$4H2O of 4.5 and 1.5 g,
antibacterial effects on assessed concentrations. Cexime as respectively, were dissolved in 15 mL distilled water with
broad-spectrum commercially available antibiotic, could inhibit vigorous stirring at room temperature, and then the iron solu-
or kill the microorganisms in concentrations ranging from 2 to 32 tion was added drop wise into the cellulose solution for 2.5 h.
mg mL1. A few studies have shown that the surface of Ag NPs can The resultant cellulose/g-Fe2O3 composites were ltered
generate free radical and induce the membrane damage subse- washed with distilled water until Cl ion was completely
quently. Also, the oxygen can easily oxidize Ag NPs to generate removed. Then, the obtained composite was loaded into 50 mL
partially oxidized Ag with chemisorbed Ag+ that would lead to the distilled water and stirred for 2 h to the dispersion of the
destruction of the cell membrane of bacteria.23–25 composite. Then, 0.2 g trisodium citrate, as stabilizer, was
added to a 20 mL of AgNO3 solution (0.05 M). Subsequently, this
solution was added to the previous solution and the resulted
Conclusions mixture was stirred for 30 min. Then, 5 mL NaBH4 was added
dropwise within 2 h. The resultant cellulose/g-Fe2O3/Ag nano-
In summary, we have introduced a new protocol for the
composite was washed with water for several time and was dried
synthesis of a biopolymer-based nanocomposite applicable
at room temperature.
either as a nanocatalyst in the synthesis of organic compounds
or as an antimicrobial agent. Efficient syntheses of 2,4,5-
trisubstituted-1H-imidazoles were carried out starting from
simple and readily available precursors including benzoin or Typical procedure for the preparation of 2,4,5-triphenyl-1H-
benzil, benzaldehyde and NH4OAc in the presence of a catalytic imidazole 4a
amount of cellulose/g-Fe2O3/Ag nanocomposite. A large The mixture of benzoin or benzil (1 mmol), a benzaldehyde
number of unique properties of this catalyst were observed (1 mmol) and ammonium acetate (2.5 mmol) was heated at 100

including short reaction times, easy workup procedure, reus- C (bath temperature) in the presence of cellulose/g-Fe2O3/Ag
ability of the catalyst, high atom economy, excellent yields and (0.015 g) under solvent-free conditions. Aer the completion of
environmentally benign reaction conditions. The antibacterial the reaction, as indicated by TLC, the resulting mixture was
tests of the nanocomposite showed a strong antimicrobial dissolved in 10 mL of EtOH and the catalyst was removed easily
activity against S. aureus (Gram-positive bacteria), and its ability by adsorbing on the magnetic stirring bar when the stirring was
to kill the bacteria in a short time. This demonstrates the stopped. Then, the resulted solution was ltered off and the
nanocomposite has a potential application in the medical and ltrate was evaporated under reduced pressure to afford a pure
health care elds. product.

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RSC Advances
Selected spectral data for 4,5-diphenyl-2-p-tolyl-1H-imidazole
(4c)
Mp: 228–230  C; FT-IR (KBr, cm1): 1446, 1496, 1600, 3033; 1H
NMR (500 MHz, CDCl3): d (ppm); 2.3 (3H, s, CH3), 7.2–7.6 (12H,
m, H–Ar), 7.7 (2H, d, J ¼ 13.0 Hz, H–Ar), 9.6 (1H, s, NH); 13C
NMR (125 MHz, CDCl3): 21.7, 125.6, 127.5, 128.2, 128.7, 128.8,
128.9, 129.1, 130.0, 139.2, 146.6.
Selected spectral data for 4,5-diphenyl-2-3-nitrophenyl-1H-
imidazole (4g)
Mp: >300  C; FT-IR (KBr, cm1): 1350, 1526, 3068, 3448; 1H NMR
(500 MHz, CDCl3): d (ppm); 6.99–7.11 (1H, d, J ¼ 13.0 Hz, H–Ar),
7.20–7.24 (1H, m, H–Ar), 7.25–7.31 (3H, m, H–Ar), 7.37 (1H, t, J
¼ 13.0 Hz, H–Ar), 7.41–7.44 (2H, t, J ¼ 12.5 Hz, H–Ar), 7.47–7.49
(3H, d, J ¼ 13.0 Hz, H–Ar), 7.51–7.53 (3H, m, H–Ar), 9.6 (1H, s,
NH); 13C NMR (125 MHz, CDCl3): 119.4, 122.6, 127.1, 128.4,
128.7, 128.9, 129.1, 130.4, 131.2, 131.8, 143.4, 148.4.
Typical procedure for the preparation of 2-(N-anilino)-2-(4-
chlorophenyl)acetonitrile (8a)
A mixture of 4-chlorobenzaldehyde (0.140 g, 1 mmol), aniline
(0.093 g, 1 mmol), and TMSCN (0.120 g, 1.2 mmol) was stirred
for 20 min in the presence of cellulose/g-Fe2O3/Ag (0.015 g)
under solvent-free conditions. Aer completion of the reaction,
as indicated by TLC, the resulting mixture was dissolved in
10 mL of EtOH and the catalyst was removed easily by adsorbing
on the magnetic stirring bar when the stirring was stopped.
Then, the resulted solution was ltered off and the ltrate was
evaporated under reduced pressure to afford a pure product.
Further purication was followed by crystallization from
ethanol to give product 4a as pale yellow crystals.
Characterization data of 2-(4-tolylamino)-2-(4-chlorophenyl)-
acetonitrile (8e)
Mp 92–94  C; FT-IR (KBr, cm1): 3348, 2925, 2366, 1627, 1525,
1497, 1096, 820; 1H NMR (500 MHz, CDCl3): dH (ppm) ¼ 2.35
(3H, s, CH3), 3.93 (1H, d, J ¼ 8.5 Hz, CH), 5.50 (1H, d, J ¼ 8.0 Hz,
NH), 6.71 (2H, d, J ¼ 8.5 Hz, H–Ar), 7.12 (2H, d, J ¼ 8.0 Hz, H–
Ar), 7.47 (2H, d, J ¼ 8.5 Hz, H–Ar), 7.59 (2H, d, J ¼ 8.5, H–Ar); 13C
NMR (125 MHz, CDCl3): 21.6, 50.1, 114.7, 118.1, 128.6, 129.5,
129.9, 130.0, 132.6, 135.5, 142.2.
Antibacterial property
Two standard bacterial strains were assessed as models of
Gram-positive (Staphylococcus aureus ATCC 25923) and Gram-
negative (Escherichia coli ATCC 25922) bacteria.
Broth micro-dilution method was performed according to
the standard protocols of CLSI (Clinical Laboratory Standard
Institute) to determine the minimum concentration of each
sample required for inhibition of visible growth of tested
bacterium (MIC) and minimum concentration of samples
which result in killing of the assessed microorganism (MBC). In
brief, two-fold serial dilutions of each sample were made in
a concentration ranging from 1024 to 0.5 mg mL1 in sterile
plastic micro-dilution trays containing Mueller Hinton broth
13664 | RSC Adv., 2016, 6, 13657–13665
Paper
(MHB). Then, bacterial suspensions of each bacterial strain
were prepared from freshly cultured bacteria in sterile normal
saline that were adjusted to 0.5 McFarland standard turbidity.
The suspension was further diluted (1 : 100) by sterile MHB just
before adding to the wells containing a serial dilution of each
sample. MICs were recorded aer 22 h incubation at 37  C as
the lowest concentration which could inhibit visible growth of
bacteria. 100 mL of all wells contained higher concentration
than MIC value were cultured onto nutrient agar plate and MBC
were recorded aer 22 h incubation at 37  C as the lowest
concentration which could kill 99.9% of assessed bacterial cells.
Cexime was used as standard antibiotic and all experiments
were done in triplicate.
Acknowledgements
The authors gratefully acknowledge the nancial support from
the Iran National Science Foundation (INSF) and partial
support from the Research Council of the Iran University of
Science and Technology.
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