Synthesis, characterization, and nonlinear optical properties of some new series of S-(5-aryl-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate derivatives

Article abstract of DOI:10.3906/kim-1811-54

In the present investigation, some novel S-(5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate (3a–3e) derivatives were synthesized and their impact on optical properties was studied. They have also been characterized by elemental analysis and various spectroscopic methods including FTIR, ¹ H NMR, ¹³ C NMR, and UV-Vis techniques. The nonlinear refractive indexes of 3a–3e were also measured in dichloromethane via Z-scan method using a continuous wave diode-pumped laser at 532 nm wavelength. The nonlinear refractive coefficient of compounds was obtained from 10¹¹ m²/W order. Regarding the appropriate nonlinearity of these compounds, they could be considered good candidates for biooptical and photonic applications. All the synthesized compounds (3a–3e) have also been evaluated for their antimicrobial and antifungal activities. The bioactive assay showed that the synthetic compounds displayed variable inhibition zones against tested bacterium Escherichia coli and fungus Aspergillus fumigatus in comparison to enrofloxacin and amphotericin as reference drugs, which are normally used for treating such infections.

Full text of DOI:10.3906/kim-1811-54

Turk J Chem
Turkish Journal of Chemistry
(2019) 43: 902 – 910
© TÜBİTAK
http://journals.tubitak.gov.tr/chem/
doi:10.3906/kim-1811-54
Research Article
Synthesis, characterization, and nonlinear optical properties of some new series of
S-(5-aryl-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate derivatives
1
2
1
Zahra Dono GHEZELBASH ,, Hamideh MOTIEI ,, Miri MAHMOODY ,,
1,∗
Karim Akbari DILMAGHANI
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran
Department of Physics, Atomic and Molecular Group, Faculty of Science, Urmia University, Urmia, Iran
,
1
2
Received: 26.11.2018
•
Accepted/Published Online: 25.03.2019
•
Final Version: 11.06.2019
Abstract: In the present investigation, some novel S-(5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate (3a–3e) deriva-
tives were synthesized and their impact on optical properties was studied. They have also been characterized by el-
1
13
emental analysis and various spectroscopic methods including FTIR, H NMR,
C NMR, and UV-Vis techniques.
The nonlinear refractive indexes of 3a–3e were also measured in dichloromethane via Z-scan method using a continu-
ous wave diode-pumped laser at 532 nm wavelength. The nonlinear refractive coefficient of compounds was obtained
from 1011 m2/W order. Regarding the appropriate nonlinearity of these compounds, they could be considered good
candidates for biooptical and photonic applications. All the synthesized compounds (3a–3e) have also been evaluated
for their antimicrobial and antifungal activities. The bioactive assay showed that the synthetic compounds displayed
variable inhibition zones against tested bacterium Escherichia coli and fungus Aspergillus fumigatus in comparison to
enrofloxacin and amphotericin as reference drugs, which are normally used for treating such infections.
Key words: Synthesis, S-(5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate, nonlinear optics, Z-scan technique, diode-
pumped laser
1. Introduction
Recently, the detection of new materials with significant nonlinearity and optical properties has gained much
attention from scientists, especially physicists and chemists. Nonlinear refraction may originate from many
1
different physical sources like electronic molecular, electrostriction, or thermal ones. During the last two
2,3
4
decades several branches of materials such as organic molecules,
organic dyes, π-conjugated organometallic
5−7
8,9
compounds and their derivatives,
and nanocomposites
have been investigated because of their exceptional
optical properties. Heterocyclic compounds are the largest classical division of medicinal chemistry studies and
some other sciences due to their biological activities and industrial importance. Oxadiazole is a versatile
heterocyclic nucleus that can be considered as a simple five-membered heterocycle containing two nitrogen
and one oxygen atoms. The oxadiazoles exist in different isomeric forms such as 1,2,5-, 1,2,3-, 1,2,4-, and
1,3,4-oxadiazoles. Among them, 1,3,4-oxadiazole derivatives are the most studied ones because of their various
chemical and pharmaceutical activities and adaptable intermediates, due to the fact that the thiol group on the
oxadiazole ring undergoes nucleophilic substitution reaction easily. The compounds possessing 1,3,4-oxadiazole
10
11
cores have a broad spectrum of biological properties including antibacterial,
antifungal,
analgesic and
∗Correspondence: k.adilmaghani@urmia.ac.ir
902
This work is licensed under a Creative Commons Attribution 4.0 International License.

GHEZELBASH et al./Turk J Chem
12,13
14
15
16
17
antiinflammatory,
antiviral, anticancer, hypoglycemic, and antimalarial properties. Development
of novel chemotherapeutic agents is an important and challenging task for medicinal chemists. The agents
originating from heterocyclic compounds are antibiotic-resistant, have good biological properties, and are
effective compounds against multidrug-resistant microbial infection. Remarkable nonlinearity arises from donor-
acceptor (D-A) electron groups. In this research the effect of donor-acceptor groups in five-ring members was
18
studied comparatively. Some of the investigated materials regarding D-A groups are acetylenes and hetero
19,20
aromatic rings.
Different methods like four-wave mixing, ellipse rotation, and Z-scan technique were used to determine
21−23
the nonlinearity of materials,
among which Z-scan is the latest and simplest method for determining both
the sign and magnitude of nonlinear coefficients. Since oxadiazole substitutes are known in today’s scientific
world, their nonlinear optical (NLO) properties are very promising for biooptical applications and use in the
24,25
field of optoelectronic, such as in optical switching and optical limiting.
In the present research, some novel S-(5-aryl-1, 3, 4-oxadiazol-2-yl) 2-chloroethanethioates (3a–3e)
were synthesized and their influence on the optical properties was studied. The new synthesized heterocyclic
1
derivatives have been characterized by elemental analysis and various spectroscopic methods including FTIR,
H
13
NMR, and C NMR techniques. The linear optical properties were also analyzed by UV-Vis spectrophotometer.
In our previous works we reported the synthesis and antibacterial properties of a new series of thioglycoside
26−29
heterocyclic derivatives of 1,2,4-triazole-5-thiones and 1,3,4-oxadiazole-5-thiones.
Following the design
and synthesis of 1,3,4-oxadiazole moieties linked to choloroactylchloride, the synthesis and nonlinear optical
properties of a series of new S-(5-aryl-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate derivatives (3a–3e) have been
reported along with the related antimicrobial activity.
2. Results and discussion
2.1. UV-Vis measurements
The electronic spectra of five samples in the 400–800 wavelength range using UV-Vis spectrophotometer are
illustrated in Figure 1. Linear absorption spectra of the samples were associated with the color of organic
compounds. Considering that our compounds are white and orange crystals, their absorption spectra are close
to each other. The absorption values of compounds at λ = 532 nm are 0.028, 0.008, 0.020, 0.084, and 0.018,
respectively.
The linear absorption coefficient α is determined by the following equation:
1
α = LnT.
(1)
L
In this equation, L is the thickness of cell equal to 1 cm and T is the transmittance of light from the cuvette.
2.2. Z-scan measurements
23
The Z-scan technique was proposed by Sheik-Bahae et al. in 1989. Figure 2 illustrates the closed aperture
Z-scan graphs of five samples at one incident intensity of laser. The intensity is the same and an aperture of the
photodiode at far field has linear transmittance of about 0.1. The curve shows a minimum transmittance (valley)
before focus and a maximum transmittance (peak) after focus that indicates formation of a self-defocusing effect.
This effect is represented by the negative nonlinear refractive coefficient (n2). Therefore, the shape of the graph
903

GHEZELBASH et al./Turk J Chem
0.25
(d)
(e)
(b)
(c)
0.2
)
(a
.2
0.1
o
400
500
600
700
800
Wavelength
nm)
(
Figure 1. Absorbance spectra of (a) Ar = phenyl, (b) 2-chlorophenyl, (c) Ar = furyl, (d) 2-nitrophenyl, and (e)
3-nitrophenyl in CH2 Cl2 .
immediately reveals the sign of the refractive index. Because of the CW laser, the temperature rises (∆T) in
the laser spot, which leads to the change in refractive index so that ∆n = (dn/dT)∆T , with dn/dT being the
thermooptic coefficient of the sample. dn/dT comes from the density change with temperature in the solution.
It is also noted that all the sample solutions have negative refractive index. In turn, this provides evidence that
the nonlinear refractive index might be related to thermal collection in the samples. In addition, compound d
has the largest absorbance at 532 nm among the five compounds, and also the magnitude of n2 in d is higher
than in others, which gives further evidence that the thermal effect is a dominant mechanism for the nonlinear
refractive index. Variations of normalized transmittance for all of the samples were recorded by photodiode.
Using the peak–valley differences (∆TP V ), variations in the phase shift can be calculated by the following
equations:
∆Tpv ≃ 0.406 (1S)0.25 |∆ϕ0|
∆ϕ0 = kn2I0Leff
(2)
(3)
Here, S is the linear transmittance of aperture of about 0.1 and ∆ϕ0 is variation of phase, k = 2π/λ is the
wave vector, I0 = P0/πω02 is the input intensity of the laser, and Leff = 1eαl/α is the effective length of the
sample. Calculated values of n2 are listed in Table 1. The theoretical fit according to Eq. (4) for all of the
30
samples was drawn to prove the appropriate consistency between experimental data and theory.
4∆ϕ0(X)2
(1 + (X)2)(9 + (X)2)
T (z) = 1
(4)
Here, X = z/z0 . Theoretical fits are plotted at ideal conditions without any errors in measuring the focal
spot radius or linear absorption index. Furthermore, there are other uncertainties in estimating exact values,
such as fluctuations of laser or voltage sources and contaminations on the cell. Therefore, there are some noises
in the experimental curves. Open aperture measurements were recorded, too. Despite good refraction, these
904

GHEZELBASH et al./Turk J Chem
Figure 2. Closed aperture curves of five compounds containing (a) Ar = phenyl, (b) 2-chlorophenyl, (c) Ar = furyl,
(d) 2-nitrophenyl, and (e) 3-nitrophenyl solved in CH2 Cl2 at I0= 89.36 kW/m2 incident intensity of laser beam.
compounds do not have good absorption, so they are neglected. The comparison of normalized transmittance
of five compounds as a function of position (z) is plotted in Figure 3.
Figure 3. Comparison of normalized transmittance of five compounds containing (a) Ar = phenyl, (b) 2-chlorophenyl,
(c) Ar = furyl, (d) 2-nitrophenyl, and (e) 3-nitrophenyl solved in CH2 Cl2 at I0= 89.36 kW/m2 incident intensity of
laser beam.
By comparing closed aperture curves of samples in Figure 3 at one intensity and results of calculations
in Table 1, it was observed that the NLO of the new synthesized compounds (a–e) was increased directly by
905

GHEZELBASH et al./Turk J Chem
(
)
Table 1. The measured values of the linear absorption coefficient α cm1 , peak–valley difference ∆TP V , and nonlinear
refraction coefficients of five compounds containing (a) Ar = phenyl, (b) 2-chlorophenyl, (c) Ar = furyl, (d) 2-
nitrophenyl, and (e) 3-nitrophenyl at I0= 89.36 kW/m2 .
(
)
Sample
(a) Ar = phenyl
α cm1
∆TP V n2(×1011 m2/W)
0.065
0.170
0.268
0.471
0.767
0.470
–6.08
(b) 2-Chlorophenyl 0.020
–9.89
(c) Ar = Furyl
(d) 2-Nitrophenyl
(e) 3-Nitrophenyl
0.047
0.193
0.041
–17.35
–29.21
–17.39
electron-withdrawing effects of substituting compounds. The NLO property of compound d is better than that
of compound e; due to the nitro position in ortho, which causes molecule formation in more resonance forms,
the electron-withdrawing effect of the furyl substitute in compound c is more than that of the 2-chloro ones in
compound b because of oxygen as a more electronegative hetero atom in the furyl ring. It is certain that the
electron traction effect of 2-chlorophenyl is stronger than that of the phenyl substitute in compound a due to
the electronegativity of the chlorine atom.
2.3. Biological studies
The in vitro antibacterial and antifungal activities of the synthesized compounds in CH3 Cl against Escherichia
coli and Aspergillus fumigatus are shown in Tables 2 and 3. The minimal inhibition concentrations (MICs) for
enrofloxacin as the reference antibacterial drug and amphotericin were 36 µg/µL and 28 µg/µL in similar test
conditions, respectively.
Table 2. In vitro antibacterial activity of synthetic compounds against E. coli.
Compound
3a 3b 3c 3d 3e
MIC (µg/µL)
MBC (µg/µL) 20 30
10 15
0
0
10
10
0
0
As shown in Table 2, these compounds showed higher antibacterial effects in comparison with enrofloxacin
and amphotericin, which are normally used for treating such infections. The best results belonged to 3d and
3a, which showed higher activity against E. coli. A zero value indicates that there were no biological activities.
Table 3. In vitro antifungal activity of synthetic compounds against Aspergillus fumigatus.
Compound
3a 3b 3c 3d 3e
MIC (µg/µL)
MFC (µg/µL)
0
0
0
0
10
20
0
0
20
40
As shown in the Table 3, these compounds showed higher antibacterial effects in comparison with
enrofloxacin and amphotericin, which are normally used for treating such infections. The best results antifungal
belonged to 3c, which showed higher activity against Aspergillus fumigatus.
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GHEZELBASH et al./Turk J Chem
2.4. Conclusions
In short, a new series of S-(5-aryl-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate derivatives (3a–3e) was prepared
by reaction of 1,3,4-oxadiazole-5-thione (2a–2e) moieties with chloroactylcholoride in the presence of potassium
carbonate solved in dimethyl-formamide at room temperature. The new compounds were characterized by
UV-Vis spectra and nonlinear optical measurements were performed by Z-scan technique. The closed aperture
curves profile reveals a self-defocusing effect by negative nonlinear refractive coefficient. However, the pattern
is typically observed by thermal lens effect. By comparison of curves, it was concluded that:
∆TP V compound d > ∆TP V compound e > ∆TP V compound c > ∆TP V compound b > ∆TP V compound a
The NLO of compounds a–e was increased directly by electron-withdrawing effects of substitutes. Because of
existing donor-accepter groups, delocalized π-electrons, etc., they become appropriate candidates for photonic
devices and biooptical applications. The antimicrobial results obtained from the novel oxadiazoles derivatives
(3a–3e) revealed that, among the synthesized compounds, 3a and 3d and 3c showed better antibacterial and
antifungal activities, respectively.
3. Experimental
3.1. General
The melting points of all compounds were recorded on a Philip Harris C4954718 apparatus without calibration.
1
FTIR spectra were determined on a Thermo Nicolet 670 Nexus spectrometer with KBr pellets. H NMR (300
13
MHz) and C NMR (75 MHz) measurements were recorded on a Bruker 300 MHz spectrometer in CDCl3
using TMS as the internal reference. Thin-layer chromatography (TLC) analysis was carried out on silica gel
plates. All chemicals were purchased from Merck (Tehran, Iran) and used as received by standard procedures.
All of the instruments, chemicals, and solvents were dried according to standard methods. Freshly distilled
solvents were used throughout the experiments and anhydrous solvents were dried according to the method of
31
Perrin and Armarego. Microanalyses were performed on a Leco Analyzer 932.
3.2. Synthesis procedures
The main route for the synthesis of 5-substituted-1,3,4-oxadiazole-2-thiols/thiones (2a–2e) involves an initial
reaction between an acylhydrazide (1a–1e) (0.1 mol) and carbon disulfide (15.2 g, 0.2 mol) in basic alcohol solu-
tion (50 mL) followed by acidification of the reaction mixture. The precipitate was filtered, washed thoroughly
with cold water, and recrystallized from ethanol to give 1,3,4-oxadiazole-5-thiones (2a–2e) (yield: 60%–70%).
32−34
The following compounds were prepared under analogous procedures.
Thiol-thione tautomerism is known
35
for compounds 2a–2e and one of the forms usually predominates (Figure 4).
3.2.1. Synthesis of S-(-5-aryl-1,3,4 oxadiazole-2-yl)2-chloroethanethioate (3a–3e)
First 1,3,4-oxadiazole-5-thione (0.01 mol) was dissolved in N,N-dimethylformamide (10 mL), and then potassium
carbonate (0.3 to 0.5 g) was added to the mixture and stirred for 30 min. Then chloro acetyl chloride (0.01
mol) was added dropwise at 0–5 °C and the mixture was stirred for 3 h at room temperature. The formation of
the intermediate was confirmed by observing the TLC using ethyl-acetate : hexane as the mobile phase. After
completion of the reaction the mixture was poured into cold water to obtain the product (Figure 4).
907

GHEZELBASH et al./Turk J Chem
MeOH/C.H2S04
reflux
reflux
(la-e)
N-
ꢂoꢃS
NH
�
1)CS2/KOH/EtOH/reflux
ꢀsꢁcı
il
/�-
1)K2co3
1
1
\
-
-
-
---
-
Arꢂ
Ar
0
l
)Hc
2) CICH2COCI/DMF
(3a-e)
(2a-e)
=
=
Ar phenyl (a), 2-chlorophenyl (b), Ar furyl (c), 2-Nitrophenyl (d), 3-Nitrophenyl (e)
Ar:
Figure 4. Synthesis of S-(5-aryl-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate derivatives.
3.2.2. Synthesis of S-(5-phenyl-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate (3a)
Yield: 0.192 g, 75%, Lit: mp 160–162 °C; IR (KBr), ?/cm−1 : 3440, 2930, 1759, 1622, 1490, 1316, 1051, 968,
1
753, 689; H NMR (300 MHz, CDCl3) δ (ppm): 4.84 (2H, s, CH2), 7.50–7.66 (3H, m, ArH), 7.94–8.02 (2H,
13
m, ArH); C NMR (75 MHz, CDCl3) δ (ppm): 172.50, 162.67, 158.81, 133.43, 132.65, 130.33, 128.24, 127.50,
125.49, 43.44. Calcd: C, 47.16; H, 2.77; N, 11.00; S, 12.59%; Found: C, 47.14; H, 2.75; N, 10.98; S, 12.58%.
3.2.3. Synthesis of S-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)2-chloroethanethioate (3b)
Yield: 0.22 g, 76%, Lit: mp 149–151 °C; IR (KBr), ?/cm−1 : 3444, 2949, 1764, 1615, 1591, 1317, 1032, 932,
1
729, 684; H NMR (300 MHz, CDCl3) δ (ppm): 4.84 (2H, s, CH2), 7.44–7.50 (1H, m, ArH), 7.54–7.63 (2H,
13
m, ArH), 7.95–7.97 (1H, d, J = 7.8 Hz, ArH); C NMR (75 MHz, CDCl3) δ (ppm): 171.56, 162.63, 156.60,
133.72, 132.90, 132.81, 132.00, 129.92, 128.48, 43.30. Calcd: C, 41.54; H, 2.09; N, 9.69; S, 11.09%; Found: C,
41.53; H, 2.07; N, 9.71; S, 11.08%.
3.2.4. Synthesis S-(5-(furan-2-yl)-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate (3c)
Yield: 0.191 g, 79%, Lit: mp 105–108 °C; IR (KBr), ?/cm−1 : 3145, 2942, 1769, 1654, 1466, 1319, 1251, 1071,
1
945, 589; H NMR (300 MHz, CDCl3) δ (ppm): 4.80 (2H, s, CH2), 6.67 (1H, s, furyl), 7.27 (1H, s, furyl), 7.73
13
(1H, s, furyl); C NMR (75 MHz, CDCl3) δ (ppm): 171.25, 149.05, 146.39, 116.79, 113.97, 113.79, 43.35.
Calcd: C, 39.28; H, 2.06; N, 11.45; S, 13.10%; Found: C, 39.27; H, 2.07; N, 11.43; S, 13.9%.
3.2.5. Synthesis S-(5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate (3d)
Yield: 0.23 g, 76%, Lit: mp 119–121 °C; IR (KBr), ?/cm−1 : 3440, 2949, 1771, 1657, 1536, 1337, 1304, 1253,
1
1042, 748, 720, 566; H NMR (300 MHz, CDCl3) δ (ppm): 4.77 (2H, s, CH2), 7.85–7.91 (3H, m, ArH),
13
8.14–8.17 (1H, m, ArH); C NMR (75 MHz, CDCl3) δ (ppm): 171.68, 162.48, 159.19, 134.70, 133.08, 132.98,
132.71, 132.63, 132.53, 132.18, 43.30. Calcd: C, 40.08; H, 2.02; N, 14.02; S, 10.70%; Found: C, 40.07; H, 2.03;
N, 14.01; S, 10.71%.
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GHEZELBASH et al./Turk J Chem
3.2.6. Synthesis S-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate (3e)
Yield: 0.21 g, 74%, Lit: mp 134–138 °C; IR (KBr), ?/cm−1 : 3332, 2945, 2875, 1723, 1537, 1470, 1354, 1286,
1
1196, 1028, 718; H NMR (CDCl3 , 300 MHz) δ (ppm): 4.77 (2H, s, CH2), 7.77 (1H, t, J = 7.8 Hz, ArH),
13
8.30 (1H, d, J = 7.5 Hz, ArH), 8.45 (1H, d, J = 8.1, ArH), 8.82 (1H, s, ArH); C NMR (75 MHz, CDCl3)
δ
(ppm): 178.23, 167.94, 162.94, 133.32, 133.26, 133.16, 124.94, 44.16. Calcd: C, 40.08; H, 2.02; N, 14.02; S,
10.70%; Found: 40.06; H, 2.03; N, 14.00; S, 10.71%.
3.3. Optical studies
In order to evaluate the sign and the magnitude of nonlinear coefficients simultaneously, the Z-scan technique
30
was used, which was developed by Sheik-Bahae et al. A schematic diagram of the Z-scan setup is shown
in Figure 5. As the sample moves towards the focusing point of the lens (f = 10 cm) in the light in the
propagating direction (arbitrary z-axis) from –z to +z, the normalized transmittance at far field varies. A
photodiode behind an aperture records the data of normalized transmittance. A power meter measures the
incident power of the laser beam.
Figure 5. A schematic diagram of Z-scan setup including BS (beam splitter), L (lens), A (aperture), and PD
(photodiode).
During the Z-scan measurement, a CW laser at a wavelength of 532 nm was used. All of the samples
were liquid, poured into a cell with 6 mm thickness. Since the Rayleigh length (z0= kω02/2) is less than the cell
30
thickness, the thin sample approximation is valid and ω0 is the beam waist at the focal point (z = 0).
3.4. Biological studies
3.4.1. Bacterial strain
The antibacterial and antifungal activities of the compounds were assayed according to our previously published
36
method. The mentioned activities were tested against E. coli and Aspergillus fumigatus.
3.4.2. Statistical analysis
All statistical analyses were performed with SPSS 11.0 for Windows (SPSS Inc., Chicago, IL, USA).
Acknowledgments
The authors are grateful to Urmia University for providing a fellowship for the present work and are also
thankful to Prof Dr Joachim Thiem from Hamburg University for some of the measurements.
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References
1. Boyd, R. Nonlinear Optics; Elsevier: Burlington, MA, USA, 2008.
2. Mande, P.; Mathew, E.; Chitrambalam, S.; Joe, I. H.; Sekar, N. Opt. Mater. 2017, 72, 549-558.
3. Tripathy, U.; Rallabandi, S.; Bisht, P. B. Opt. Mater. 2017, 72, 233-240.
4. Motiei, H.; Jafari, A.; Naderali, R. Opt. Laser. Technol. 2017, 88, 68-74.
5. Teimuri, R.; Rahimpour, K.; Ghadari, R.; Kandjani, S. A. Mol. Liq.J. 2017, 244, 322-329.
6. Teimuri, R.; Rahimpour, K.; Poursadegh, A. Mater. Chem. Phys. J. 2017, 200, 384-394.
7. Zhang, Y. D.; Zhao, Z. Y.; Yao, C. B.; Yang, L.; Li, J.; Yuan, P. Opt. Laser. Technol. 2014, 58, 207-214.
8. Naderali, R.; Jafari, A.; Motiei, H. Appl. Phys. B. J. 2015, 120, 681-687.
9. Sousani, A.; Motiei, H.; Najafimoghadam, P.; Hasanzade, R. Opt. Mater. 2017, 67, 172-179.
10. Ansari, K. F.; Lal, C. Eur. J. Med.Chem. 2009, 44, 4028-4033.
11. Sharma, C. M.; Dharm Kohli, V.; Sharma, S. Drug. Del. J. 2010, 2, 265-277.
12. Hui, X. P.; Chu, C. H.; Zhang, Z. Y. Indian J. Chem. 2002, 41, 2176-2179.
13. Burbuliene, M. M.; Jakubkiene, V.; Mekuskiene, G.; Udrenaite, E.; Smicius, R.; Vainilavicius, P. Il Farmaco 2004,
59, 767-774.
14. Biradar, J. S.; Sasidhar, B. S.; Parveen, R. Eur. J. Med. Chem. 2010, 45, 4074-4078.
15. Aboraia, S.; Abdel-Rahman, H. M.; Mahfouz, N. M.; El-Gendy, M. A. Med. Chem. 2006, 14, 1236-1246.
16. Sahin, G.; Palaska, E.; Kelicen, P.; Demirdamar, R.; Altinok, G. Drug Res. 2001, 51, 478-484.
17. Liu, M.; Wilairat, P.; Go, L. M. J. Med. Chem. 2010, 44, 4443-4452.
18. Cheng, L. T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.; Rikken, G.; Marder, S. R. Phys. Chem. J. 1991, 95,
10631-10643.
19. Mandal, K.; Kar, T.; Nandi, P. K.; Bhattacharyya, S. P. Chem. Phys. Lett. 2003, 376, 116-124.
20. Rao, V. P.; Jen, A. K. Y.; Wong, K. Y.; Drost, K. Chem. Commun. J. 1993, 14, 1118-1120.
21. Kuciauskas, D.; Porsch, M. J.; Pakalnis, S.; Lott, K. M.; Wright, M. E. Phys. Chem. B. J. 2003, 107, 1559-1566.
22. Williams, W. E.; Soileau, M. J.; Van Stryland, E. W. Opt. Commun. 1984, 50, 256-260.
23. Sheik-Bahae, M.; Said, A. A.; Van Stryland, E. W. Opt. Lett. 1989, 14, 955-957.
24. Nikogosian, D. N. Nonlinear Optical Crystals: A Complete Survey; Springer-Science: New York, NY, USA, 2005.
25. Jain, K.; Pratt, G. W. Appl. Phys. Lett. 1976, 28, 719-721.
26. Dilmaghani, K. A.; Nasuhi Pur, F.; Hataminezhad, M. Iran. J. Pharm. Res. 2015, 14, 693-699.
27. Dilmaghani, K. A.; Nasuhi Pur, F.; Hoseini, N.; Alavi, A.; Niknam, Z.; Mir Fakahraee, F. Phosphorus Sulfur Silicon
Relat. Elem. 2014, 189, 81-87.
28. Dilmaghani, K. A.; Nasuhi Pur, F.; Mahammadpour, M.; Mahammadnejad, J. Iran. J. Pharm. Res. 2016, 15,
777-782.
29. Ghezelbash, Z. D.; Dilmaghani, K. A. Acta Chim. Slov. 2016, 63, 790-797.
30. Sheik-Bahae, M.; Said, A. A.; Wei, T. H.; Hagan, D. J.; Van Stryland, E. W. IEEE J. Quantum. Electron. 1990,
26, 760-769.
31. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: Oxford, UK, 1988.
32. Iqbal, R.; Zamani, K.; Rama, N. H. Turk. J. Chem. 1988, 20, 295-301.
33. Al-Joubory, I. K. J.; Albayati, T. F. K.; Albayati, K. A. J.; Al-Joubory, T. S. M.; Diyala, J. R. For. Pure Sci.
2013, 9, 47-56.
34. Lee, C. H.; Cho, H. I.; Lee, K. J. Bull. Korean. Chem. Soc. 2001, 22, 1153-1155. 35. Koparır, M.; Çetin, A.; Cansız,
A. Molecules 2005, 10, 475-480.
35. Tukmechi, A.; Ownagh, A.; Mohebbat, A. Braz. J. Microbiol. 2010, 41, 1086-1092.
910