Optimization, Spectroscopic (Excited States, UV/Vis, Polarization) Studies, FMO, ELF, LOL, QTAIM, NBO Analysis and Elect
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TRUCTURE OF MATTER AND QUANTUM CHEMISTRY
Optimization, Spectroscopic (Excited States, UV/Vis, Polarization) Studies, FMO, ELF, LOL, QTAIM, NBO Analysis and Electronic Properties of Two New Azomethine Derivatives: A Theoretical and Experimental Investigations Siyamak Shahaba,b,c,*, Masoome Sheikhid,**, Liudmila Filippovicha, Evgenij Dikusara, Mahdieh Darroudie, Sadegh Kavianif, Mikhail Atroshkoc, and Marina Drachilovskayac a Institute
of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, 220072 Republic of Belarus of Chemistry of New Materials, National Academy of Sciences of Belarus, Minsk, 220141 Republic of Belarus c Belarusian State University, ISEI BSU, Minsk, Republic of Belarus d Young Researchers and Elite Club, Gorgan Branch, Islamic Azad University, Gorgan, Iran e Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416 Iran f Department of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran * e-mail: [email protected] ** e-mail: [email protected]
bInstitute
Received July 17, 2019; revised July 17, 2019; accepted February 11, 2020
Abstract—In the current study, the molecular structures of the two new azomethine dyes such as AAFOH-1 and AAFOH-2 have been investigated with the use of density functional theory (DFT/B3LYP/6-311+G(d)) in a DMSO solvent for the first time. The electronic spectra of the new dyes in a DMSO solvent were carried out by temporally dependent density functional theory (TD-DFT) method. The computed absorption spectral data of the investigated molecules are in good agreement with the experimental data, thus allowing an assignment of the UV/Vis spectra. The equilibrium geometry, the HOMO and LUMO molecular orbitals, excitation energies, oscillator strengths and natural bond orbital (NBO) analysis for the molecules have also been calculated and presented. The electron location function (ELF), localized orbital locator (LOL), and quantum theory of atoms in molecules (QTAIM) analyses were also carried out. On the basis of polyvinyl alcohol (PVA) and the new synthesized azomethine dyes polarizing films were developed. The main optical parameters of polarizing PVA-films (transmittance, polarization efficiency, and dichroic ratio) have been measured and discussed. Anizotropy of thermal conductivity of the PVA-films have been studied. Keywords: azomethine, HOMO–LUMO, UV/Vis spectrum, TD-DFT, polarization, QTAIM analysis DOI: 10.1134/S0036024420090241
1. INTRODUCTION Azo compounds are one of the most significant organic dyes that containing nitrogen as the azo (‒N=N–) group. Azomethine is functional group Nbased 1,3-dipoles containing of an iminium ion connected to a carbanion. Azomethine used in 1,3-dipolar cycloaddition reactions to form 5-membered heterocycles, consisting pyrrolidines and pyrrolines [1, 2]. These compounds are one of the largest and most diverse combinations of synthetic organic dyes are being used today [3]. Azo compounds are extremely significant and are moderately strong and chemically stabl
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