Materials Today: Proceedings 64 (2022) 605–610

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Materials Today: Proceedings

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Nonlinear optical properties of chalcone derivatives-a short review

Amrita Saha ⇑
Department of Science & Humanities, MLR institute of Technology, Hyderabad, Telangana 500043, India

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

Article history: Chalcones are significant entities in the synthetic pathway of several heterocyclic molecules and well-
Received 12 April 2022 known moiety for its versatile biological and pharmacological activities e.g., anticancer, antioxidant,
Received in revised form 21 April 2022 anti-inflammatory, antimicrobial, antiallergic, and antimalarial activities etc. The chemical structure of
Accepted 9 May 2022
chalcone comprises open chain flavonoids, where a, b unsaturated carbonyl, having three carbons, motif
Available online 27 May 2022
links two rings who are aromatic in nature. a, b unsaturated keto group present in chalcones are respon-
sible for their diverse antimicrobial activity.
Keywords:
A huge amount of research is done on the biological activity of chalcones and very few material prop-
Chalcone
Nonlinear optical Property
erties of chalcone are explored. Among the material properties, one of the most interesting properties is
Chromophore its nonlinear optical properties. The exploration started long back in the nineties century and a review
would clear the picture of the present scenario of where we were and where we can head with the non-
linear properties of chalcone derivatives.
The design strategy obtained from the review of the past research work shows that chalcone core is a
useful NLO chromophore. For bridging/ linking moiety, an alkene-bridge has been found to be more effec-
tive link compared to an alkyne-bridge. The higher degree of conjugation, which is an inherent property
of ethylene-linked p systems is found to be the reason behind its effectiveness. Dialkyl and diaryl donors
have been found more effective than oxygen-based donors, phenoxide is the strongest donor. D
p
D
and D
p
A
p
D are significantly operative than A
p
A and A
p
D
p
A. Conjugation
Signature (Sc) is the measure of effective conjugation length. Rigid conformations of p bridge systems
are more effective than flexible ones.
Copyright Ó 2022 Elsevier Ltd. All rights reserved.
Selection and peer-review under responsibility of the scientific committee of the International Confer-
ence on Advanced Materials for Innovation and Sustainability.

1. Introduction: tron source have been porphyrins, phthalocyanines, fused-

Study of interaction of light in matter has always been a topic of
curiosity. The fascinating phenomenon of nonlinear optics (NLO) is
pulling extensive research towards itself for its applications in ver-
satile new areas which encircles biological imaging, two photon up
conversion lasing, optical power limiting, two-photon fluorescence
excitation microscopy, 3D micro fabrication, and PDT. The hunt for
organic molecules, consisting molecular wires, which have slackly
attached electron systems, with a robust optical response; with
efficient 2PA cross-sections/coefficients is the current technologi-
cal demand for use in NLO. [1–12] An excellent review by Danniel
et al identified that structures consisting of oxygen-based acceptor
groups and planar p electron source have better efficiency to show
higher TPA cross section. Though in major researches, the p elec-
thiophenes, fluorene and pentacene. But the major disadvantages
of poor yield, oxidative instability, insolubility have to be resolved.
Another issue that needs to address is the molecular weight of the
designed motif, as large molecules should be avoided in order to
achieve high end application.[11].
Previous study carried out to explore NLO activity of organic
molecules is covered in this review, the chalcone derivatives are
mainly focused on getting an idea of its extent of optical nonlinear-
ity observed so far. As the luminescent property is also intercon-
nected to NLO activity, few examples of chalcone based
luminescent compounds is also incorporated. Besides chalcone
based materials, the optical nonlinearity of few other classes of
compounds is also discussed.

⇑ Corresponding author.
E-mail address: dramrita@mlrinstitutions.ac.in

https://doi.org/10.1016/j.matpr.2022.05.131
2214-7853/Copyright Ó 2022 Elsevier Ltd. All rights reserved.
Selection and peer-review under responsibility of the scientific committee of the International Conference on Advanced Materials for Innovation and Sustainability.
A. Saha Materials Today: Proceedings 64 (2022) 605–610

1.1. SHG property of ethoxy & methoxyphenyl chalcone

Kitaoka et al., (1990) had synthesized and grown large single

crystal of 3-(4-methoxyphenyl)-1-(4-ethoxyphenyl)prop-2-en-1-one,
structure of the molecule is shown in Fig. 1.
The operative NLO coefficients (deff) of both type I and II were
assessed to be 3.5 and 5.7 pm/V correspondingly. For a single shot, Fig. 2a. Molecular Structure of l-(3-thienyl)-3-(4-methylphenyl)-2-propen-l-one.
the laser damage threshold was over 30 GW/cm2 compared to a
1.053 lm laser with pulse width of 1 ns, which is higher compared
to inorganic crystals like potassium dihydrogen phosphate (KDP)
crystal and fused silica. The efficiency of SHG was 8.9 times, mea-
sured by using the powder technique, higher than that of the urea.
The chalcone derivative was also found to be chemically stable.
[12].

1.2. Laser properties of the single crystal l-(3-thienyl)-3-(4- Fig. 2b. Molecular Structure of l-(3-thienyl)-3-(4-chlorophenyl)-2-propen-l-one
chlorophenyl)-2-propen-l-one

Kitaoka et al., (1991) studied the laser properties of the single

crystal, Figs. 2a, 2b, 2c thienylchalcone at a wavelength of
1064 nm. Laser properties includes transmittance, angular and
temperature acceptances, productive nonlinear coefficient, walk-
off angle etc were measured. The cut-off wavelength was
430 nm; the NLO coefficient (deff) was 7.1 pm/V; i.e., 1.7 times,
compared to KTP. It was proposed as a beneficial nonlinear crystal
Fig. 2c. l-(3-thienyl)-3-(4-bromophenyl)-2-propen-l-one.
which can produce green and blue lasers [13].
Uchida et al., (1998) had resolute crystal structures using X-ray
analysis of some SHG-active chalcone derivatives. The direction of
phase matching for the crystals [l-(3-thienyl)-3-(4-bromophenyl)-2-
propen-l-one] and [l-(3-thienyl)-3-(4-chlorophenyl)-2-propen-l-one],
Fig. 3, was conversed by concerning its nature of packing in crystal.
They found that molecule having higher value of twisting angle
possesses a lower value of SHG, the probable reason can be a smal-
ler number of conjugated p electrons. [14]. Fig. 3. 1-(4-methoxyphenyl)-3-(phenyl)-2-propen-1-one.

1.3. Second harmonic generation conversion efficiency of 4-

methoxyphenyl chalcone derivative
Indira et al., (2002) explored the second harmonic generation
conversion efficiency of 1-(4-methoxyphenyl)-3-(phenyl)-2-propen-
1-one, Fig. 3, in powder state.
This single crystal’s SHG efficiency was calculated by powder
technique with Nd:YAG laser (laser power = 13 mJ/s), the efficacy
was 0.8 times compared to urea.[15].
1.4. NLO properties of 1–3-diaryl- propenones
Kiran et al., (2007) explored the Nonlinear properties of diaryl-
chalcones at 532 nm via ns, Z-scan method. These compounds had
4-methylthiophenyl substituent in the structure. This group
recorded the third order NLO response with strong TPA (two-
photon absorption). The p-electron density was varied in these
conjugated materials and this was the reason for their NLO
response.
The compounds shown in Fig. 4 showed very good optical lim-
iting properties. v(3) was found to be dependent on the D and A
present in the aromatic ring. This is turn reflects that the com-
Fig. 1. Molecular Structure of (E)-3-(4-ethoxyphenyl)-1-(4-methoxyphenyl)prop-
2-en-1-one.
606
pound has electronic nonlinearity. When the substituent was t-
butyl group [4/-tert- butyl thienyl chalcone], the nonlinear refrac-
tive index, n2, changed drastically, highest in the series recorded as

2.033  10
11 esu. [16].
1.5. Third order NLO properties of 40 -methoxy chalcone
Ravindra et al., (2007) have explored the NLO properties of 40 -
methoxy chalcone along with some derivatives of methoxy chal-
cone, Fig. 5. The NLO response in this series of suitably substituted
compounds increased when the electron acceptor or donor
strength was increased, in D
A
A or D-A-D system and the
NLO response was measured in the order of 10
13 esu. [17].
1.6. Third order NLO properties of dimethylamino
dibenzylideneacetone
Kiran et al., (2008) synthesised this chalcone derivative, p-(N,N-
dimethylamino) dibenzylideneacetone.
The compound, Fig. 6, when doped in poly(methyl methacry-
late), showed high third-order nonlinear
susceptibility  10
12 esu. Nd:YAG laser, single-beam z-scan and
degenerate four wave mixing methods with nano second laser
pulses at 532 nm.
The doped polymer had negative nonlinear refractive index. The
compound displays strong RSA with good OL property. How the
NLO parameters were dependent on concentration has been pre-
sented in the research work. [18].
A. Saha
Fig. 4. Molecular structures of 1–3-diaryl- propenones containing 4-methylthiophenyl compounds.
Fig. 5. Molecular Structure of 40 -methoxy chalcone.
Fig. 6. Molecular structure of p-(N,N-dimethylamino) dibenzylideneacetone.
1.7. Optical nonlinearities of chalcone derivatives with 4/ position
substituted with 3,4,5-Trimethoxy group
Gu et al., (2008) studied optical nonlinearities of para substi-
tuted trimethoxy chalcone compounds in near IR region by z-
scan method, fs laser pulses, the 2PA cross section r2PA in chal-
cones raised as the substituent was changed with higher acceptor
strength.
The molecules represent D
A
A type structures. The com-
pound is designed as 3, 4, 5-trimethoxy group, fluorine/ chlorine/
amino group are substituted at one end of the derivative with
the –CO group at the centre. For D
A
A type molecules, end to
end charge transfer takes place in the molecule. Electron acceptor
groups are responsible for the observed enrichment in the nonlin-
ear response. The amino group is a stronger electron acceptor
Fig. 7. Molecular Structure of 4/ substituted 3,4,5-trimethoxy chalcone derivatives.
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Materials Today: Proceedings 64 (2022) 605–610
(5.79  10
33 esu) than chlorine and fluorine (2.62  10
33 esu),
Fig. 7. The charge transfer was more effective in amino substituent.
And it exhibits higher nonlinear response than both the fluoro
(4.01  10
33 esu) and chloro derivative, Fig. 8. Chlorine has stron-
ger inductive effect compared to -F group, the CT in chloro deriva-
tive is more the fluoro derivative. So, chloro derivative exhibited a
higher nonlinear response than fluoro derivative. [19].
1.8. Optical nonlinearities of 2,4,5-trimethoxy-4/-nitrochalcone
Gu et al., (2009) checked the optical nonlinearities of
trimethoxy-para-nitrochalcone, Fig. 8, in the near IR range, z-scans
was carried out with fs laser pulses, at lower intensity of laser,
third-order nonlinearity was leading, if laser intensity exceeded a
critical value, both 3rd and 5th order nonlinearities were prevail-
ing. This chalcone derivative belongs to D-p-A type motif. The tri-
methoxy group and the nitro group has electron donating and
accepting ability respectively, whereas electron is withdrawn by
-C = O bond from the system.[20].
1.9. Second harmonic generation (SHG) efficiency
Ravindra et al., (2009) synthesized chalcone co-crystal, Fig. 9;
NLO efficiency of this derivative was 7 times higher than urea.
Molecular dipoles arranged themselves in head-to-tail manner
and this unidirectional alignment added the dipole moment of
individual molecule and established a net polarization. N–H  O
H-bond relations helped in maintaining the orientation. This polar-
ization is responsible for large SHG efficiency.
This single crystal also showed third-order NLO response &
good OL at 532 nm. Two-photon induced ESA, which led to RSA,
is accountable for optical limiting property. The structure–prop-
A. Saha
Fig. 8. Molecular Structure of 2,4,5-trimethoxy-4/-nitrochalcone.
erty connection among this series of chalcone and related deriva-
tives was discoursed on the basis of experimental findings and
semi-empirical hyperpolarizability calculations.
They summarized that if the phenylene group is substituted,
rather than at the benzoyl group, with strong electron donor, its
more effective. When the numeral value of methoxy substituent
was increased at the phenylene side it had no effect in augmenting
NLO response, rather only one methoxy group was enough in
enhancing NLO properties. [21].
2. Second harmonic generation (SHG) efficiency of
Dicinnamalacetone
Bhadauria et al., (2011) prepared Dicinnamalacetone, Fig. 10,
where two benzene units are connected with -C = O group conju-
gated alternate double bonds. The SHG power of 2.17 was approx-
imately twice of urea. Their experimental data suggested that the
SHG property is influenced by the charge transfer within the mole-
cule. [22].
2.1. NLO property of chalcone Co-crystal
D’silva et al., (2011) performed a z-scan experiment with a
picosecond (ps) at a wavelength of 800 nm. ßeff = 5  10
12 cm W
1
& n2 = 3.257  10
12 esu was derived from the z-scan technique.
In this chalcone co-crystal, Fig. 11, the para position has elec-
tron donating -Br and -Cl groups in the benzoyl ring. Compared
to chloro or bromo substituent, -SCH3 has higher electron donating
ability. Donor-p-Acceptor-p-Donor (D-p-A-p-D) motif was created
by the substituent present in the co-crystal (-C = O substituent
which accepts electron at the centre with donors at the end of
the molecule), where the direction of CT was from donor to the
acceptor located at the centre. The donor attached to phenylene
side showed stronger CT to the –CO group compared to the benzoyl
group. This charge transfer was responsible for the NLO property.
[23].
Fig. 9. Molecular Structure of Chalcones showing Second Harmonic Generation (SHG) Efficiency.
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Materials Today: Proceedings 64 (2022) 605–610
Fig. 10. Molecular Structure of Dicinnamalacetone.
2.2. SHG efficiency of (E)-1-(4-methoxyphenyl)-3-(2,3,5-
trichlorophenyl)prop-2-en-1-one
Kumar et al., (2011) prepared a single crystal of p-
methoxyphenyl-trichlorophenyl chalcone, Fig. 12, which belonged
to a space group Cc and monoclinic system. They studied SHG test
with Kurtz powder technique. The crystal was hard, NLO active, the
efficiency was three times of urea, good thermal stability and suit-
able for device application. SHG response originated from its struc-
tural features.
It was observed that the molecule had D-A-D arrangement; tri-
chlorophenyl group has mesomeric electron releasing behaviour
and can act as donor group. The centre of the molecule has car-
bonyl group (-C = O) and can act as electron accepting group. So,
transfer of charge may take place from the ends to centre. This
ensured the delocalization of electron within the molecule, differ-
ent polarization & therefore optical non-linearity.
Moreover, in addition to C-H----O hydrogen bond interactions,
weak C-H---p bond (benzene ring as p centre) crystal lattice has
intermolecular interactions, this made the crystal align in head-
to-tail manner within the structure. These interactions facilitated
extended charge transfer within the supramolecule which in turn
stretched delocalization in the ground and excited state. This
resulted in improved SHG efficiency. [24].
2.3. SHG efficiency of 1-(4-methylthiophenyl)-3-(4-methoxyphenyl)
prop-2-en-1-one
Kumar et al., (2012) synthesized 1-(4-methylthiophenyl)-3-(4-
methoxyphenyl)prop-2-en-1-one, Fig. 13, the crystal of space group
Pna21. The compound does not absorb in the visible range. The
chalcone derivative exhibited NLO activity and its efficiency was
3.15 times to that of urea. The fundamental beam power, crystal
size, field-gain coefficient, minimum beam waist influenced the
SHG conversion efficiency.
The refractive index was measured by Brewster’s angle method.
SHG measurement was performed with a Q-switched Nd:YAG
laser, wavelength of 1064 nm, 8 ns pulse width and pulse of
10 Hz. The effect of the substituents like methoxy and thiomethoxy
on the structural property & non-linearity was discussed in detail.
[25].
A. Saha
Fig. 11. Molecular structure of Chalcone Co-Crystals.
Fig. 12. Molecular Structure of (E)-1-(4-methoxyphenyl)-3-(2,3,5-trichlorophenyl)
prop-2-en-1-one.
Fig. 13. Molecular Structure of 1-(4-methylthiophenyl)-3-(4-methoxyphenyl)prop-
2-en-1-one.
2.4. NLO property of 1-(4-chlorophenyl)-3-(4-dimethylaminophenyl)
prop-2-en-1-one
Janardhana et al., (2013) 1-(4-chlorophenyl)-3-(4-dimethylamino
phenyl)prop-2-en-1-one, Fig. 14. The crystal is monoclinic & falls in
P21/c space group. Through Z-scan measurements, the NLA and
nonlinear refraction coefficients were measured. Closed aperture
data displayed negative value of nonlinear refraction coefficient
(c); (c) = -1.89  10
20 m2V
2; ß= 0.58  10
20 m2V
2. [26]
2.5. NLO property of 1-(5-bromothiophen-2-yl)-3-(4-nitrophenyl)
prop-2-en-1-one
Prabhu et al., (2013) synthesized a new NLO active organic com-
pound, bromothiophenyl-nitrophenyl chalcone, Fig. 15. X-ray stud-
ies found that, the crystal is triclinic with a noncentrosymmetric
space group of P1. The crystal’s SHG efficiency, measured by Nd:
YAG laser & powder technique, was four times of urea.
Thiophene ring was substituted with bromine at an end acted as
a donor of electron the introduction of electron acceptor nitro sub-
stituent at the other end of the aryl ring enhanced the nonlinearity
considerably. [27].
2.6. Two-Photon absorption or 2PA assisted E.S absorption of bromo
substituted chalcone
Janardhana et al., (2013) synthesized chalcone based NLO mate-
rial, 4-{(1E, 3Z)-3-(4-bromo phenyl]-3-[2-(2, 4-dinitrophenyl)
hydrazinylidene] prop-1-en-1-yl}phenol, Fig. 16, and studied their
Fig. 14. Molecular structure of 1-(4-chlorophenyl)-3-(4-dimethylaminophenyl)
prop-2-en-1-one.
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Materials Today: Proceedings 64 (2022) 605–610
Fig. 15. molecular Structure of 1-(5-bromothiophen-2-yl)-3-(4-nitrophenyl) prop-
2-en-1-one.
Fig. 16. Molecular Structure of 4-{(1E, 3Z)-3-(4-bromo phenyl]-3-[2-(2, 4-dinitro-
phenyl) hydrazinylidene] prop-1-en-1-yl}phenol.
NLA using a nano second laser & z-scan technique. The nonlinear
absorption instigated from 2PA or 2P assisted E.S absorption. [28].
3. Conclusion
Based on the detailed review of the pat work the following
design strategy can be obtained for a useful NLO chromophore.
For bridging/ linking moiety, an alkene-bridge has been found
to be more effective link compared to an alkyne-bridge. The higher
degree of conjugation, which is an inherent property of ethylene-
linked p systems is found to be the reason behind its effectiveness.
Dialkyl and diaryl donors have been found more effective than
oxygen-based donors, phenoxide is the strongest donor.
D
p
D and D
p
A
p
D have higher effectiveness
compared to the systems where Acceptor and Donor are arranged
in A
p
A and A
p
D
p
A way.
Conjugation Signature (Sc) is the measure of effective conjuga-
tion length. When the molecule under study in completely conju-
gated, then Sc / N 4e , for systems containing chromophoric units
which are small in terms of conjugation or with systems having
cross conjugation, then Sc / N e . For oligomers, the relation stands
to be Sc / N ke , integer k varies from 1 to 4. If N e is increased in a ser-
ies of linear oligomers, the value of ‘k’ changes from 4 to 1.
Rigid conformations of p bridge systems are more effective than
flexible ones.
CRediT authorship contribution statement
Amrita Saha: Conceptualization, Methodology, Software, Data
curation, Writing – original draft, Visualization, Investigation, Val-
idation, Writing – review & editing.
A. Saha
Declaration of Competing Interest
The authors declare that they have no known competing finan-
cial interests or personal relationships that could have appeared
to influence the work reported in this paper.
Acknowledgements
A. Saha would like to thank Department of Science and Technol-
ogy, India for INSPIRE FELLOWSHIP; Grant no- DST/INSPIRE Fellow-
ship/2012/149 and Assam University, Silchar for lab facilities and
Dr. Sudip Choudhury for his valuable suggestions.
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