PCM-DFT Investigation on the Linear and Nonlinear Optical Properties of Two Triazole Derivatives in Different Solvents

Authors

  • Ítalo N. Ribeiro Laboratório de Modelagem Molecular Aplicada e Simulação (LaMMAS), Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil https://orcid.org/0000-0003-0721-1284
  • Fernando C.G. Murga Laboratório de Modelagem Molecular Aplicada e Simulação (LaMMAS), Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil https://orcid.org/0000-0003-4736-092X
  • Marcos V.C.S. Rezende Laboratório de Modelagem Molecular Aplicada e Simulação (LaMMAS), Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil https://orcid.org/0000-0001-9158-3384
  • Andreia R. dos Santos Laboratório de Modelagem Molecular Aplicada e Simulação (LaMMAS), Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil https://orcid.org/0000-0002-6714-7512
  • Juliana G. de Morais Laboratório de Modelagem Molecular Aplicada e Simulação (LaMMAS), Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil https://orcid.org/0000-0002-7741-8267
  • Jeziel R. dos Santos Laboratório de Modelagem Molecular Aplicada e Simulação (LaMMAS), Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil https://orcid.org/0000-0002-3147-4757
  • Ricardo Ternavisk Laboratório de Modelagem Molecular Aplicada e Simulação (LaMMAS), Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil https://orcid.org/0000-0003-3711-3650
  • Basilio Baseia Departamento de Física, Universidade Federal da Paraíba, 58.051-970, Jo ao Pessoa, PB, Brazil; Instituto de Física, Universidade Federal de Goiás, 74.690-900, Goiânia, GO, Brazil https://orcid.org/0000-0002-2464-9889
  • Francisco A.P. Osório Instituto de Física, Universidade Federal de Goiás, 74.690-900, Goiânia, GO, Brazil; Pontifícia Universidade Católica de Goiás, 74605-010, Goiânia, GO, Brazil https://orcid.org/0000-0003-3009-9593
  • Clodoaldo Valverde Laboratório de Modelagem Molecular Aplicada e Simulação (LaMMAS), Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil; Universidade Paulista (UNIP), 74845-090, Goiânia, GO, Brazil https://orcid.org/0000-0002-1656-4981

DOI:

https://doi.org/10.26713/jamcnp.v8i2.1609

Keywords:

Polarizable continuum model, Dipole moment, Linear polarizability, Hyper-Rayleigh Scattering (HRS), Second hyperpolarizability

Abstract

This effort was performed to investigate the linear and nonlinear optical (NLO) properties of two 1,2,3-triazole derivatives in several solvent media and in gas-phase at PCM/DFT/CAM-B3LYP/6-311+G(d) level of theory. The static and dynamic NLO parameters as the total dipole moment, the average linear polarizability, the Hyper-Rayleigh Scattering (HRS) first hyperpolarizability, and the average second hyperpolarizabilityare calculated as function of static dielectric constant of the solvents. The computational linear and nonlinear optical studies revealed that both the triazoles derivatives are promising materials for NLO applications.

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References

L. M. G. Abegão, R. D. Fonseca, T. N. Ramos, F. Mahuteau-Betzer, S. Piguel, J. Joatan R. (Jr.), C. R. Mendonça, S. Canuto, D. L. Silva and L. De Boni, Oxazole Dyes with Potential for Photoluminescence Bioprobes: A Two-Photon Absorption Study, Journal of Physical Chemistry C 122 (2018), 10526 – 10534, DOI: 10.1021/acs.jpcc.8b01904.

W. Bartkowiak and J. Lipi ´ nski, Finite-field calculations of the second-order hyperpolarizabilities ° of molecules in solutions, Chemical Physics Letters 292 (1998), 92 – 96, DOI: 10.1016/S0009-2614(98)00669-1.

R. Bersohn, Y. Pao and H. L. Frisch, Double-quantum light scattering by molecules, The Journal of Chemical Physics 45 (1966), 3184, DOI: 10.1063/1.1728092.

R. Cammi and J. Tomasi, Remarks on the use of the apparent surface charges (ASC) methods in solvation problems: Iterative versus matrix-inversion procedures and the renormalization of the apparent charges, Journal of Computational Chemistry 16 (1995), 1449 – 1458, DOI: 10.1002/jcc.540161202.

J. M. F. Custodio, G. D. C. D’Oliveira, F. Gotardo, L. H. Z. Cocca, L. De Boni, C. N. Perez, L. J. Q. Maia, C. Valverde, F. A. P. Osório and H. B. Napolitano, Chalcone as potential nonlinear optical material: A combined theoretical, structural, and spectroscopic study, The Journal of Physical Chemistry C 123 (2019), 5931 – 5941, DOI: 10.1021/acs.jpcc.9b01063.

V. V. Dodonov, C. Valverde, L. S. Souza and B. Baseia, Classicalization times of parametrically amplified “Schrödinger cat” states coupled to phase-sensitive reservoirs, Physics Letters A 375 (2011), 3668, DOI: 10.1016/j.physleta.2011.08.058.

V. V. Dodonov, C. Valverde, L. S. Souza and B. Baseia, Decoherence of odd compass states in the phase-sensitive amplifying/dissipating environment, Annals of Physics 371 (2016), 296 – 312, DOI: 10.1016/j.aop.2016.04.019.

I. S. Dogan, Z. Özdemir, S. Sari, I. Bozbey, A. Karakurt and S. Saraç, Synthesis, anticonvulsant activity, and molecular modeling studies of novel 1-phenyl/1-(4-chlorophenyl)-2-(1H-triazol-1-yl)ethanol ester derivatives, Medicinal Chemistry Research 27 (2018), 2171 – 2186, DOI: 10.1007/s00044-018-2225-6.

M. Er, A. M. Abounakhla, H. Tahtaci, A. H. Bawah, S. S. Çinaroglu, A. Onaran and A. Ece, An integrated approach towards the development of novel antifungal agents containing thiadiazole: synthesis and a combined similarity search, homology modelling, molecular dynamics and molecular docking study, Chemistry Central Journal 12 (2018), Article number: 121, DOI: 10.1186/s13065-018-0485-3.

M. Á. Farrán, M. Á. Bonet, R. M. Claramunt, M. C. Torralba, I. Alkorta and J. Elguero, The structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer’s disease, Acta Crystallographica Section C: Structural Chemistry 74 (2018), 513 – 522, DOI: 10.1107/S2053229618004394.

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery (Jr.), J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Gaussian, Inc., Wallingford CT, (2009), URL: https://gaussian.com/glossary/g09/.

O. Gómez-García, D. Andrade-Pavón, E. Campos-Aldrete, R. Ballinas-Indilí, A. Méndez-Tenorio, L. Villa-Tanaca and C. Álvarez-Toledano, Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines, Molecules 23 (2018), 599, DOI: 10.3390/molecules23030599.

Y.-Y. He, J. Chen, X.-L. Zheng, X. Xu, W.-Q. Li, L. Yang andW. Q. Tian, Spiral graphene nanoribbons with azulene defects as potential nonlinear optical materials, ACS Applied Nano Materials 2 (2019), 1648 – 1654, DOI: 10.1021/acsanm.9b00089.

J. Jeyaram, K. Varadharajan, B. Singaram and R. Rajendhran, Growth and characterization of organic second order nonlinear optical (NLO) 4-chloroanilinium-L-tartrate monohydrate single crystals, Journal of Crystal Growth 486 (2018), 96 – 103, DOI: 10.1016/j.jcrysgro.2018.01.015.

K. Karypidou, S. R. Ribone, M. A. Quevedo, L. Persoons, C. Pannecouque, C. Helsen and F. Claessens, Synthesis, biological evaluation and molecular modeling of a novel series of fused 1,2,3-triazoles as potential anti-coronavirus agents, Bioorganic & Medicinal Chemistry Letters 28 (2018), 3472 – 3476, DOI: 10.1016/j.bmcl.2018.09.019.

E. É. Klen, I. L. Nikitina, N. N. Makarova, A. F. Miftakhova, O. A. Ivanova, F. A. Khaliullin and E. K. Alekhin, 3-substituted thietane-1,1-dioxides: Synthesis, antidepressant activity, and in silico prediction of their pharmacokinetic and toxicological properties, Pharmaceutical Chemistry Journal 50 (2017), 642 – 648, DOI: 10.1007/s11094-017-1506-6.

T. K. Kuruvilla, J. C. Prasana, S. Muthu, J. George and S. A. Mathew, Quantum mechanical and spectroscopic (FT-IR, FT-Raman) study, NBO analysis, HOMO-LUMO, first order hyperpolarizability and molecular docking study of methyl[(3R)-3-(2-methylphenoxy)-3-phenylpropyl]amine by density functional method, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 188 (2018), 382 – 393, DOI: 10.1016/j.saa.2017.07.029.

C. F. Macrae, I. Sovago, S. J. Cottrell, P. T. A. Galek, P. McCabe, E. Pidcock, M. Platings, G. P. Shields, J. S. Stevens, M. Towler and P. A. Wood, Mercury 4.0: from visualization to analysis, design and prediction, Journal of Applied Crystallography 53 (2020), 226 – 235, DOI: 10.1107/S1600576719014092.

B. Mennucci, R. Cammi and J. Tomasi, Medium effects on the properties of chemical systems: Electric and magnetic response of donor-acceptor systems within the polarizable continuum model, International Journal of Quantum Chemistry 75 (1999), 767 – 781, DOI: 10.1002/(SICI)1097-461X(1999)75:4/5%3C767::AID-QUA43%3E3.0.CO;2-L.

S. Miertuš, E. Scrocco and J. Tomasi, Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects, Chemical Physics 55 (1981), 117 – 129, DOI: 10.1016/0301-0104(81)85090-2.

E. Rtibi, M. Abderrabba, S. Ayadi and B. Champagne, Theoretical assessment of the second-order nonlinear optical responses of Lindqvist-type organoimido polyoxometalates, Inorganic Chemistry 58 (2019), 11210 – 11219, DOI: 10.1021/acs.inorgchem.9b01857.

S. Sert-Ozgur, B. C. Tel, E. I. Somuncuoglu, I. Kazkayasi, M. Ertan and B. Tozkoparan, Centennial anniversary of Mannich’s report on the formation of (beta)-amino-ketones in the Archiv der Pharmazie, Archiv der Pharmazie 350 (2017), e1700052, DOI: 10.1002/ardp.201700152.

D. L. Silva, R. D. Fonseca, M. G. Vivas, E. Ishow, S. Canuto, C. R. Mendonca, D. L. Silva, R. D. Fonseca, M. G. Vivas, E. Ishow, S. Canuto and L. De Boni, Experimental and theoretical investigation of the first-order hyperpolarizability of a class of triarylamine derivatives, The Journal of Chemical Physics 142 (2015), 064312, DOI: 10.1063/1.4906893.

J. Tomasi, B. Mennucci and R. Cammi, Quantum mechanical continuum Solvation models, Chemical Reviews 105 (2005), 2999 – 3094, DOI: 10.1021/cr9904009.

C. Tonnelé, B. Champagne, L. Muccioli and F. Castet, Second-order nonlinear optical properties of Stenhouse photoswitches: insights from density functional theory, Physical Chemistry Chemical Physics 20 (2018), 27658 – 27667, DOI: 10.1039/C8CP05843A.

C. Travelli, S. Aprile, R. Rahimian, A. A. Grolla, F. Rogati, M. Bertolotti, F. Malagnino, R. di Paola, D. Impellizzeri, R. Fusco, V. Mercalli, A. Massarotti, G. Stortini, S. Terrazzino, E. Del Grosso, G. Fakhfouri, M. P. Troiani, M. A. Alisi, G. Grosa, G. Sorba, P. L. Canonico, G. Orsomando, S. Cuzzocrea, A. A. Genazzani, U. Galli and G. C. Tron, Identification of Novel Triazole-Based Nicotinamide Phosphoribosyltransferase (NAMPT) inhibitors endowed with antiproliferative and antiinflammatory Activity, Journal of Medicinal Chemistry 60 (2017), 1768 – 1792, DOI: 10.1021/acs.jmedchem.6b01392.

C. Valverde, F. A. P. Osório, T. L. Fonseca and B. Baseia, DFT study of third-order nonlinear susceptibility of a chalcone crystal, Chemical Physics Letters 706 (2018), 170 – 174, DOI: 10.1016/j.cplett.2018.06.001.

C. Valverde, Í. N. Ribeiro, J. V. B. Soares, B. Baseia and F. A. P. Osório, Prediction of the linear and nonlinear optical properties of a Schiff base derivatives via DFT, Advances in Condensed Matter Physics 2019 (2019), Article ID 8148392, DOI: 10.1155/2019/8148392.

C. Valverde, S. A. de Lima e Castro, G. R. Vaz, J. L. de A. Ferreira, B. Baseia and F. A. P. Osório, Third-order Nonlinear optical properties of a carboxylic acid derivative, Acta Chimica Slovenica 65 (2018), 739 – 749, DOI: 10.17344/acsi.2018.4462.

C. Valverde, V. G. Gonçalves and B. Baseia, Controlling the non-classical properties of a hybrid Cooper pair box system and an intensity dependent nanomechanical resonator, Physica A: Statistical Mechanics and its Applications 446 (2016), 171 – 181, DOI: 10.1016/j.physa.2015.11.027.

M. G. Vivas, R. D. Fonseca, J. de P. Siqueira, C. R. Mendonça, P. Rodrigues and L. De Boni, Femtosecond two-photon absorption spectroscopy of poly(fluorene) derivatives containing benzoselenadiazole and benzothiadiazole, Materials 10 (2017), 512, DOI: 10.3390/ma10050512.

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Published

2021-10-31
CITATION

How to Cite

Ribeiro, Ítalo N., Murga, F. C., Rezende, M. V., Santos, A. R. dos, Morais, J. G. de, Santos, J. R. dos, Ternavisk, R., Baseia, B., Osório, F. A., & Valverde, C. (2021). PCM-DFT Investigation on the Linear and Nonlinear Optical Properties of Two Triazole Derivatives in Different Solvents. Journal of Atomic, Molecular, Condensed Matter and Nano Physics, 8(2), 175–236. https://doi.org/10.26713/jamcnp.v8i2.1609

Issue

Vol. 8 No. 2 (2021)

Section

Research Article

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