Dihetarylethene photocyclization as a synthetic route to fluorescent compounds

Dihetarylethene photocyclization as a synthetic route to fluorescent compounds Full article

Journal

Journal of Photochemistry and Photobiology A-chemistry
ISSN: 1010-6030 , E-ISSN: 1873-2666

Output data

Year: 2019, Volume: 369, Pages: 34-43 Pages count : 10 DOI: 10.1016/j.jphotochem.2018.10.017

Authors

Melekhina Valeriya G. ¹ , Mityanov Vitaly S. ^2,1 , Fakhrutdinov Artem N. ¹ , Lyssenko Konstantin A. ³ , Barachevsky Valery ⁴ , Valova Tatyana ⁴ , Martynov Igor ⁴ , Ayt Anton ⁴ , Krayushkin Michail M. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp., 47, Moscow 119991, Russian Federation
2	Department of Fine Organic Synthesis and Chemistry of Dyes, D. Mendeleyev University of Chemical Technology of Russia, Miusskaya Sq., 9, Moscow 125047, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str., 28, 119991 Moscow, Russian Federation
4	Photochemistry Centre, Federal Scientific Research Centre “Crystallography and Photonics”, Novatorov Str.,7a, bld.1, 119421 Moscow, Russian Federation

It was shown that UV irradiation of imidazoline-bridged dihetarylethenes affords fused products exhibiting fluorescence. The starting compounds were prepared by three-component condensation of N,N’-dimethylurea with arylglyoxals and enols. A method was proposed for the synthesis of polycyclic imidazole derivatives by photoinduced cyclization followed by elimination of a water molecule. The advantages of the method include readily accessible starting compounds, process simplicity, and the ease of isolation of the target products. The crystal structure of the cyclization products was determined. It was shown that unlike the starting imidazol-2-ones, all photochemically prepared polycyclic products exhibit intense fluorescence.

Melekhina V.G. , Mityanov V.S. , Fakhrutdinov A.N. , Lyssenko K.A. , Barachevsky V. , Valova T. , Martynov I. , Ayt A. , Krayushkin M.M.
Dihetarylethene photocyclization as a synthetic route to fluorescent compounds
Journal of Photochemistry and Photobiology A-chemistry. 2019. V.369. P.34-43. DOI: 10.1016/j.jphotochem.2018.10.017 WOS Scopus OpenAlex

Web of science:	WOS:000454963000005
Scopus:	2-s2.0-85054589627
OpenAlex:	W2897625390

DB	Citing
OpenAlex	18
Scopus	18