Electron deficient 5-hydroxy-1,2-dihydroisoquinolin-1-ones – A new class of fluorescent dyes with large Stokes shifts

Electron deficient 5-hydroxy-1,2-dihydroisoquinolin-1-ones – A new class of fluorescent dyes with large Stokes shifts Full article

Journal

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

Output data

Year: 2021, Volume: 187, Article number : 109107, Pages count : DOI: 10.1016/j.dyepig.2020.109107

Authors

Belyy Alexander Y. ¹ , Platonov Dmitry N. ¹ , Salikov Rinat F. ¹ , Trainov Konstantin P. ¹ , Medvedev Michael G. ¹ , Luponosov Yuriy N. ² , Svidchenko Evgeniya A. ² , Tomilov Yury V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp, 119991, Moscow, Russian Federation
2	N. S. Enikolopov Institute of Synthetic Polymeric Materials, Russian Academy of Sciences, 117393, Moscow, Russian Federation

A novel class of fluorescent electron-deficient 5-hydroxyisoquinolones is proposed. The new luminophores are obtained via the reaction of stable and easily available hepta(methoxycarbonyl)cycloheptatrienyl potassium with alkylamines, anilines and acylhydrazines. The new one-pot protocol is efficient with a large scope of primary amines. The solvolysis of N-acylamino substituted 5-hydroxyisoquinolones and subsequent reactions have provided a pathway to further functionalization. Nearly all compounds have demonstrated fluorescence with considerably large the Stokes shifts (up to 6169 cm−1) except for those containing a nitro group as well as O-substituted products. In most other cases neither quantum yield nor absorption and emission maxima nor the Stokes shifts substantially depended on the substituent at the isoquinolinone ring nitrogen atom.

Belyy A.Y. , Platonov D.N. , Salikov R.F. , Trainov K.P. , Medvedev M.G. , Luponosov Y.N. , Svidchenko E.A. , Tomilov Y.V.
Electron deficient 5-hydroxy-1,2-dihydroisoquinolin-1-ones – A new class of fluorescent dyes with large Stokes shifts
Dyes and Pigments. 2021. V.187. 109107 . DOI: 10.1016/j.dyepig.2020.109107 WOS Scopus OpenAlex

≡ Web of science:	WOS:000618738000010
≡ Scopus:	2-s2.0-85099307228
≡ OpenAlex:	W3121009343