The solid state structure and environmental polarization effect of a novel asymmetric azine

Valverde, Clodoaldo; Vaz, Wesley F.; Custódio, Jean M. F.; Duarte, Vitor S.; Carvalho, Paulo S.; Figueredo, Andreza S.; Aquino, Gilberto L. B.; Baseia, B.; Napolitano, Hamilton B.

doi:10.1039/c7nj00618g

Cited by 23 publications

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“…Here we consider a single BRC molecule and through the CHELPG scheme the crystalline environment polarization is simulated by considering the atoms that surrounding the BRC molecule as point charges. The SM approach was used in several theoretical works ,,− ,− and the obtained results were found close to the experimental ones. Particularly in ref , the DFT/CAM-B3LYP/6-311++G(d,p) results for the nonlinear third-order susceptibility for a chalcone derivative have described satisfactorily the Z -scan experimental result of Prahbu et al…”

Section: Theoretical Calculations: Linear and Nonlinear Optical Prope...supporting

confidence: 62%

Chalcone as Potential Nonlinear Optical Material: A Combined Theoretical, Structural, and Spectroscopic Study

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In this work, we propose the synthesis of a novel bromine chalcone (E)-3-(2-bromophenyl)-1-(2-((phenylsulfonyl)amine))phenyl)prop-2-en-1-one (BRC) that has been crystallized by the slow evaporation technique. The second-order molecular optical scattering and two-photon absorption(2PA) spectrum of the BRC molecule dissolved in dimethyl sulfoxide (DMSO) were evaluated by using hyper-Rayleigh scattering and the femtosecond tunable Z-scan techniques. The first-order hyperpolarizability of BRC dissolved in DMSO was estimated by using a simplified two-level model, in which one- and two-photon absorption parameters were used as input information to the model. The BRC crystal was characterized from single-crystal X-ray diffraction (XRD) and spectroscopy analyzes. Also, the thermogravimetric analyses and the fluorescence spectra were obtained. In addition, an ab initio calculation method, which includes the Møller–Plesset perturbation theory (MP2) and the density functional theory (DFT) at the CAM-B3LYP level, was used to estimate the crystal linear refractive index and the third-order electric susceptibility. Also, the average first hyperpolarizability of BRC molecules dissolved in DMSO was calculated and compared with the experimental results. The obtained values are good and qualify the BRC crystal as a potential candidate for application in nonlinear optical devices.

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Section: Theoretical Calculations: Linear and Nonlinear Optical Prope...supporting

confidence: 62%

Chalcone as Potential Nonlinear Optical Material: A Combined Theoretical, Structural, and Spectroscopic Study

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“…The polarization of the crystalline environment was simulated by the supermolecule (SM) approach where the atoms of the molecules within the asymmetric unit are considered as point charges. This approach has been used in several works. − ,− In ref , the authors showed that SM approach simulates the dipole moment with results close to the experimental values and in refs and , the authors simulate the macroscopic properties χ (1) and χ (2) of the crystal, with results close to those of experiments. Other techniques to calculate the macroscopic properties χ (1) and χ (2) can also be cited, e.g., the works by Seidler and Champagne. , However, although the SM has provided good results, it is worth mentioning that other factors can also affect the nonlinear properties of the crystal.…”

Section: Experimental and Computational Proceduresmentioning

confidence: 79%

“…The value of χ (3) (−ω;ω,ω,−ω)=75645 ( pm / V ) 2 , a value 1.8 times greater than the novel asymmetric azine, 5.0 times greater than the novel amino chalcone, 8.91 times greater than the fluoro- N -acylhydrazide derivative, and 39.79 times greater than the value for the l -arginine phosphate monohydrate crystal . When we compare the third-order electric susceptibility, measured via the z -scan technique of chalcones derived from 4Br4MSP, 3Br4MSP, 4N4MSP, CTDMP, and 3MPNP, respectively, the value for NMZ is 328.89, 380.12, 319.17, 31.74, and 2.73 times higher than those values, respectively.…”

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confidence: 99%

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Using the Supermolecule Approach To Predict the Nonlinear Optics Potential of a Novel Asymmetric Azine

et al. 2018

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Organic molecules with electron acceptors or withdrawal substituents terminal at π-conjugated system are promising candidates to be explored as materials with high linear and nonlinear optical properties. On the basis of these features, a novel asymmetric azine (7E, 8E)-2-(3-methoxy-4-hydroxy-benzylidene)-1-(4nitrobenzylidene)hydrazineC 15 H 13 N 3 O 4 (NMZ) was synthesized. The molecular structure of NMZ was elucidated by X-ray crystallography and the supramolecular arrangement was analyzed from Hirshfeld surface methodology. An iterative electrostatic scheme using a super molecule approach, where neighboring molecules are represented by charge points, was employed to investigate optical dipole moment (μ), the linear polarization (α) and the first (β) and second (γ) hyperpolarizabilities. The NMZ crystallized in the centrosymetric space group P2 1 /n and packs viaand N•••π interactions. The macroscopic property of third order χ (3) found for the NMZ is 298.62 times greater than values reported for chalcone derivative (2E)-1-(3-bromophenyl)-3-[4 (methylsulfanyl)phenyl]prop-2en-1-one. The results for NMZ indicate a good nonlinear optical effect.

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“…The interest in molecules and crystals that exhibit efficient nonlinear optical properties (NLO) has grown substantially in the last two decades [1][2][3][4][5][6][7][8][9], which is mainly due to their potential applications in optoelectronic and optical devices such as light emitting diodes, photo detectors, solar cells, laser generators, biosensors, optical computing, optical communications and optical storage [1][2][3][4][5][6][7][8][9][10][11][12]. The development of new materials, whose parameters allow their use in the field of photonics for nonlinear second-order optical applications, requires the knowledge of the nonlinear polarization properties of the constituent molecules [13].…”

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Study of the hyper-Rayleigh scattering first hyperpolarizability of a chalcone derivative in various solvent media

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In this work we investigate the solvent media effects on the nonlinear optical properties of a chalcone derivative, (2E)-3-(3-methylphenyl)-1-(4-nitrophenyl) prop-2-en-1-one (3MPNP), using the polarizable continuum model (PCM) at DFT/B3LYP/6-311+G(d) level. The behavior of the hyper-Rayleigh scattering first hyperpolarizability and the average second hyperpolarizability, are studied as function of the dielectric constant of the solvent medium in both dynamic and static cases. Full Text: PDF ReferencesL. R. Almeida et al., "Synthesis, structural characterization and computational study of a novel amino chalcone: a potential nonlinear optical material", New J. Chem., vol. 41, no. 4, pp. 1744-1754, 2017. CrossRef P. K. Murthy et al., "An analysis of structural and spectroscopic signatures, the reactivity study of synthetized 4,6-dichloro-2-(methylsulfonyl)pyrimidine: A potential third-order nonlinear optical material", J. Mol. Struct., vol. 1186, pp. 263-275, Jun. 2019. CrossRef J. Kongsted, A. Osted, K. V Mikkelsen, and O. Christiansen, "“Second harmonic generation second hyperpolarizability of water calculated using the combined coupled cluster dielectric continuum or different molecular mechanics methods", J. Chem. Phys., vol. 120, no. 8, pp. 3787-98, Feb. 2004. CrossRef T. L. Fonseca, J. R. Sabino, M. A. Castro, and H. C. Georg, "A theoretical investigation of electric properties of L-arginine phosphate monohydrate including environment polarization effects", J. Chem. Phys., vol. 133, no. 14, pp. 1-8, 2010. CrossRef A. KARAKAŞ, Z. E. KOÇ, M. FRIDRICHOVÁ, P. NĚMEC, and J. KROUPA, "THE INVESTIGATION OF SECOND-ORDER NONLINEAR OPTICAL PROPERTIES OF P-NITROPHENYLAZOANILINE: SECOND HARMONIC GENERATION AND AB INITIO COMPUTATIONS", J. Theor. Comput. Chem., vol. 11, no. 01, pp. 209-221, Feb. 2012. CrossRef T. Seidler, K. Stadnicka, and B. Champagne, "Second‐order Nonlinear Optical Susceptibilities and Refractive Indices of Organic Crystals from a Multiscale Numerical Simulation Approach", Adv. Opt. Mater., vol. 2, no. 10, pp. 1000-1006, Oct. 2014. CrossRef L. M. G. Abegão et al., "Second- and third-order nonlinear optical properties of unsubstituted and mono-substituted chalcones", Chem. Phys. Lett., vol. 648, pp. 91-96, Mar. 2016. CrossRef W. F. Vaz et al., "Synthesis, characterization, and third-order nonlinear optical properties of a new neolignane analogue", RSC Adv., vol. 6, no. 82, pp. 79215-79227, 2016. CrossRef C. Valverde et al., "The solid state structure and environmental polarization effect of a novel asymmetric azine", New J. Chem., vol. 41, no. 19, pp. 11361-11371, 2017. CrossRef P. N. Prasad, D. J. Williams, and others, Introduction to nonlinear optical effects in molecules and polymers, vol. 1. Wiley New York etc., 1991. DirectLink P. Günter, Nonlinear Optical Effects and Materials, 4th ed. Berlin: Springer Berlin Heidelberg, 2000. CrossRef H. Inan et al., "Photonic crystals: emerging biosensors and their promise for point-of-care applications", Chem. Soc. Rev., vol. 46, no. 2, pp. 366-388, 2017. CrossRef H. J. Chang et al., "Chiral Nonlinear Optics in Oxides, Polymers and Liquid Crystals", J. Korean Phys. Soc., vol. 43, no. 4, p. 587, 2003. DirectLink R. Bersohn, Y. Pao, and H. L. Frisch, "Double‐Quantum Light Scattering by Molecules", J. Chem. Phys., vol. 45, no. 9, pp. 3184-3198, Nov. 1966. CrossRef K. Clays and A. Persoons, "Hyper-Rayleigh scattering in solution", Phys. Rev. Lett., vol. 66, no. 23, pp. 2980-2983, 1991. CrossRef J. Campo, F. Desmet, W. Wenseleers, and E. Goovaerts, "Highly sensitive setup for tunable wavelength hyper-Rayleigh scattering with parallel detection and calibration data for various solvents", Opt. Express, vol. 17, no. 6, p. 4587, Mar. 2009. CrossRef S. R. Prabhu, A. Jayarama, K. Chandrasekharan, V. Upadhyaya, and S. W. Ng, "Synthesis, growth, structural characterization, Hirshfeld analysis and nonlinear optical studies of a methyl substituted chalcone", J. Mol. Struct., vol. 1136, pp. 244-252, May 2017. CrossRef K. Clays and A. Persoons, "Hyper‐Rayleigh scattering in solution", Rev. Sci. Instrum., vol. 63, no. 6, pp. 3285-3289, Jun. 1992. CrossRef K. Clays et al., "Nonlinear Optical Properties of Proteins Measured by Hyper-Rayleigh Scattering in Solution", Science (80-. )., vol. 262, no. 5138, pp. 1419-1422, Nov. 1993. CrossRef M. Frisch et al., Gaussian, Inc., Wallingford CT, 2009. DirectLink J. M. F. Custodio et al., "Chalcone as Potential Nonlinear Optical Material: A Combined Theoretical, Structural, and Spectroscopic Study", J. Phys. Chem. C, vol. 123, no. 10, pp. 5931-5941, Mar. 2019. CrossRef

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The solid state structure and environmental polarization effect of a novel asymmetric azine

Abstract: Extensive solid state characterization of a novel asymmetric azine and its environmental polarization effect is reported.

Cited by 23 publications

References 51 publications

Chalcone as Potential Nonlinear Optical Material: A Combined Theoretical, Structural, and Spectroscopic Study

Chalcone as Potential Nonlinear Optical Material: A Combined Theoretical, Structural, and Spectroscopic Study

Using the Supermolecule Approach To Predict the Nonlinear Optics Potential of a Novel Asymmetric Azine

Study of the hyper-Rayleigh scattering first hyperpolarizability of a chalcone derivative in various solvent media

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