Novel push-pull fluorescent dyes – 7-(diethylamino)furo- and thieno[3,2-c]coumarins derivatives: structure, electronic spectra and TD-DFT study

Novel push-pull fluorescent dyes – 7-(diethylamino)furo- and thieno[3,2-c]coumarins derivatives: structure, electronic spectra and TD-DFT study Full article

Journal

Journal of Molecular Structure
ISSN: 0022-2860 , E-ISSN: 1872-8014

Output data

Year: 2018, Volume: 1160, Pages: 215-221 Pages count : 7 DOI: 10.1016/j.molstruc.2018.01.086

Authors

Akchurin Igor O. ¹ , Yakhutina Anna I. ¹ , Bochkov Andrei Y. ¹ , Solovjova Natalya P. ¹ , Medvedev Michael G. ^2,3 , Traven Valerii F. ¹

Affiliations

1	D. Mendeleev University of Chemical Technology, Higher Chemical College of RAS, Miusskaya sq 9, Moscow 125047, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds RAS, Vavilova str 28, Moscow 119991, Russian Federation
3	N.D.Zelinsky Institute of Organic Chemistry RAS, Leninsky Prospect 47, Moscow 119991, Russian Federation

Novel push-pull fluorescent dyes – 7-(diethylamino)furo- and 7-(diethylamino)thieno[3,2-c]coumarins derivatives have been synthesized using formyl derivatives of furo- and thieno[3,2-c]coumarins as starting materials. Electron absorption and fluorescent spectra of the dyes have been recorded in different solvents. Structure and solvent effects on the dyes spectral characteristics were analyzed. The fusion of five-membered heterocycle to coumarin provides a definite increase of Stokes shifts in all solvents and results in higher quantum yields of fluorescence. The absorption and emission bands of thieno[3,2-c] coumarin derivatives are definitely shifted to the red region (3–30 nm) compared to similar derivatives of furo[3,2-c]coumarin. TD-DFT calculations of some of the studied compounds have shown that hybrid DFT functionals and adequate representation of molecular environment are essential for obtaining accurate UV–Vis absorption spectra for the dyes with extended π-system. The longest-wave electron transitions in the studied compounds were computationally shown to be of push-pull nature.

Akchurin I.O. , Yakhutina A.I. , Bochkov A.Y. , Solovjova N.P. , Medvedev M.G. , Traven V.F.
Novel push-pull fluorescent dyes – 7-(diethylamino)furo- and thieno[3,2-c]coumarins derivatives: structure, electronic spectra and TD-DFT study
Journal of Molecular Structure. 2018. V.1160. P.215-221. DOI: 10.1016/j.molstruc.2018.01.086 WOS Scopus OpenAlex

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