Photochemical protonation of an azahelicene in 1,2-dichloroethane

Photochemical protonation of an azahelicene in 1,2-dichloroethane Full article

Journal

Journal of Photochemistry and Photobiology A: Chemistry
ISSN: 1010-6030

Output data

Year: 2025, Volume: 459, Article number : 116106, Pages count : 9 DOI: 10.1016/j.jphotochem.2024.116106

Authors

Tamozhnikova Veronica S. ^1,2 , Grivin Vjacheslav P. ² , Tsentalovich Yuri P. ³ , Yu. Balakhonov Roman ⁴ , Mekeda Igor S. ⁴ , Shirinian Valerii Z. ⁴ , Glebov Evgeni M. ^1,2

Affiliations

1	Novosibirsk State University, 2 Pirogova Str., 630090 Novosibirsk, Russian Federation
2	V.V. Voevodsky Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 Institutskaya Str., 630090 Novosibirsk, Russian Federation
3	International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a Institutskaya Str., 630090 Novosibirsk, Russian Federation
4	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky Prosp., Moscow, 119991, Russian Federation

Heterocyclic analogues of phenanthridine are an important class of nitrogen-containing compounds with promising optical properties including high quantum yield of luminescence, high molar absorption coefficients and sensitivity to solvent medium. The luminescent properties of phenanthridine and its derivatives can be changed by introducing appropriate substituents into various positions of the phenanthridine framework. Recently developed luminescent azahelicenes of furoquinoline series demonstrate strong acidochromic effect both on absorption and emission spectra. One of the features of these compounds is the photochemical formation of a protonated form in chlorine-containing solvents under UV irradiation. In this work we perform a mechanistic study of 3-methoxy-6-(4-methoxyphenyl)naphtho[1′,2′:4,5]furo[2,3-c]quinoline (compound 1) in 1,2-dichloroethane (1,2-DCE) by means of stationary and laser flash photolysis. In addition to the triplet state formation observed in typical organic solvents photoexcitation in 1,2-DCE was found to result in an electron transfer from the excited compound 1 to a solvent molecule. Reactions of resulting intermediates lead to the formation of the protonated azahelicene. The quantitative mechanism of photoprotonation is put forward.

Tamozhnikova V.S. , Grivin V.P. , Tsentalovich Y.P. , Yu. Balakhonov R. , Mekeda I.S. , Shirinian V.Z. , Glebov E.M.
Photochemical protonation of an azahelicene in 1,2-dichloroethane
Journal of Photochemistry and Photobiology A: Chemistry. 2025. V.459. 116106 :1-9. DOI: 10.1016/j.jphotochem.2024.116106 WOS Scopus

Published print:

Feb 1, 2025

Web of science:	WOS:001343669300001
Scopus:	2-s2.0-85207026279

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