A unique small molecule class of fluorophores with large Stokes shift based on the electron deficient 9-methoxypyrroloisoquinolinetrione core

A unique small molecule class of fluorophores with large Stokes shift based on the electron deficient 9-methoxypyrroloisoquinolinetrione core Научная публикация

Журнал

Dyes and Pigments
ISSN: 1873-3743 , E-ISSN: 0143-7208

Вых. Данные

Год: 2022, Том: 203, Номер статьи : 110344, Страниц : DOI: 10.1016/j.dyepig.2022.110344

Авторы

Khitrov Michael D. ^1,2 , Platonov Dmitry N. ² , Belyy Alexander Yu ² , Trainov Konstantin P. ² , Velmiskina Julia A. ^3,2,4 , Medvedev Michael G. ² , Salikov Rinat F. ² , Tomilov Yury V. ²

Организации

1	Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow, 119991, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, 119991, Russian Federation
3	D. Mendeleev University of Chemical Technology of Russia, Higher Chemical College of the Russian Academy of Sciences, Zelinsky Street 38-8, 80, Moscow, 11733, Russian Federation
4	X-ray Structural Laboratory, A.N. Nesmeyanov Institute of Organoelement Compounds RAS, Vavilov St. 28, Moscow, Russian Federation

A novel fluorescent core based on electron-deficient 9-methoxypyrroloisoquinolinetrione moiety with a condensed imide cycle is developed. The new class of dyes show large Stokes shift up to 6519 cm-1 (Δλ up to 130 nm), however, unlike parent 5-hydroxyisoquinolones, 9-methoxypyrroloisoquinolinetrione are not superphotoacidic which could be responsible for the large Stokes shifts. At the same time methylation of 5-hydroxyisoquinolones reduces Stokes shift from 5086 to 4689 cm-1. The increase in Stokes shift upon the formation of an imide cycle was shown to be due to unusual bond-lengths relaxation involving the imide ring.

Khitrov M.D. , Platonov D.N. , Belyy A.Y. , Trainov K.P. , Velmiskina J.A. , Medvedev M.G. , Salikov R.F. , Tomilov Y.V.
A unique small molecule class of fluorophores with large Stokes shift based on the electron deficient 9-methoxypyrroloisoquinolinetrione core
Dyes and Pigments. 2022. V.203. 110344 . DOI: 10.1016/j.dyepig.2022.110344 WOS Scopus OpenAlex

≡ Web of science:	WOS:000798980900007
≡ Scopus:	2-s2.0-85129678338
≡ OpenAlex:	W4224277817