Люмінесцентні властивості заміщених 4-амiнофталiмiдiв: розрахунки та експеримент

• Дата: 2020
• Автори: Zhuk, Tatyana S., Lanovenko, Svetlana V., Pashenko, Oleksandr Ye., Fokin, Andrey A.
• Формат: Стаття
• Мова: English
• Опубліковано: National University of Pharmacy 2020
• Теми: експериментальні спектри люмінесценції; поглинання; флуоресценція; cтоксові зсуви; 4-амінофталіміди; час-залежна теорія функціоналу густини; модель поляризованого континууму; УДК 547.1-304.2 539.196.5
• Онлайн доступ: https://ophcj.nuph.edu.ua/article/view/ophcj.20.189458
• Назва журналу: Journal of Organic and Pharmaceutical Chemistry

Aim. To perform a combined experimental and computational study on the luminescent properties of practically important class of organic dyes – 4-aminophthalimides.Results and discussion. The absorption and fluorescence spectra of 4-aminophthalimide derivatives in polar protic and aprotic solvents were computed and matched vs. the experimental data. The changes in emission spectra are mainly related to the NH2-group derivatization. The methyl substitution of amide hydrogen causes a batochromic shift of about 7 nm in the absorption peak and a negligible hypsochromic shift in the fluorescence peak, while introducing alkyl substituents to the amine moiety causes bathochromic shifts in absorption and emission peaks of 30 – 40 nm and 10 – 60 nm, respectively.Experimental part. Absorption and emission wavelengths were computed by the standard algorithm based on the ground state geometry optimization (equilibrium solvation), vertical excitation with nonequilibrium solvation, and the TD-DFT geometry optimization of the excited state structures. A reliable hybrid B3LYP functional was used in combination with DZ and TZ-quality basis sets.Conclusions. The computed absorption wavelengths are in excellent agreement with the experimental data and are only slightly solvent-dependent. At the same time, the discrepancy with the experiment for Stokes shifts reaches about 20 % at IEF-PCM-TD-B3LYP/6-31G(d). However, the general tendency for both absorption and fluorescence wavelengths is identical for all solvents within one molecule. Received: 24.12.2019Revised: 31.01.2020Accepted: 27.02.2020