A combined theoretical and experimental investigation on the solvatochromism of fused chromene-furanopyran: Determination of dipole moments, DFT/TD-DFT, chemical reactivity and Fukui Function

被引:2
作者
Siziani, Dhaouya [1 ,2 ]
Abdi, Yamina [1 ,2 ]
Bezzina, Belgacem [3 ,4 ]
Attou, Zineb [2 ]
Bensouilah, Nadjia [1 ,2 ,5 ]
Boutemeur, Baya [2 ]
机构
[1] Ecole Natl Super Technol Avancees, Ex Ctr Biomed, Appl Sci Lab LSA, Cite Diplomat, Algiers, Algeria
[2] Univ Sci & Technol Houari Boumediene, Fac Chem LAOC, Lab Appl Organ Chem, USTHB, PB 32, Algiers 16111, Algeria
[3] Res Ctr Ind Technol CRTI, POB 64, Algiers 16014, Algeria
[4] Univ 08 May 1945 Guelma, Fac Math Informat & Mat Sci, Dept Mat Sci, Lab Computat Chem & Nanostruct LCCN, Guelma, Algeria
[5] Univ 08 May 1945 Guelma, Lab Appl Chem LAC, Guelma, Algeria
关键词
Chromene-3-carbonitriles; Furanopyran-2-one; Solvatochromic effect; Dipole moments; DFT; Fukui indices; FLUORESCENT; SHIFT; COUMARIN; ACID; DERIVATIVES; ABSORPTION; MOLECULES; PARAMETER; SPECTRA;
D O I
10.1016/j.molstruc.2024.139473
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
This work focuses on the steady-state optical absorption and fluorescence spectra of three amino aryl-4H-furo [3,2-c]pyran -4H-chromene-3-carbonitrile derivatives. The ground state (mu g) and excited state (mu e) dipole moments were determined by the solvatochromic shift method using Kawski-Bilot and Ravi et al. equations. The excited-state dipole moment was found to be larger than that of the ground-state. The measured ground and excited state dipole moments as well as the different photophysical parameters do adequately reflect the results obtained from the computational methods. Frontier Molecular Orbitals (FMOs) analysis, the Fukui indices, COSMO-RS exploration, and Hirschfield population analysis were investigated. In order to gain a deeper understanding of the source of reactivity in the three molecules, the COnductor-like Screening MOdel for Real Solvents (COSMO-RS) was used. It is important to note that the COSMO-RS analysis of three chromenes is in complete agreement with the Hirschfield population analysis.
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页数:14
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