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4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for NIR-Emitting Push-Pull Dipolar Fluorophores.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 Aug 16; Vol. 84 (16), pp. 9965-9974. Date of Electronic Publication: 2019 Aug 01. - Publication Year :
- 2019
-
Abstract
- In the context of molecular engineering of push-pull dipolar dyes, we introduce a structural modification of the well-known electron-accepting group 2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran ( TCF ). Introduction of a (benzo[ d ]thiazol-2-yl) moiety failed, and unexpected structures were obtained. On the other hand, phenylthio and phenylsulfonyl entities were successfully introduced at position 3 of the 2-(dicyanomethylidene)-2,5-dihydrofuran ring, giving access to new electron-acceptor groups and dipolar fluorophores displaying near-infrared emission in solution or in the solid state, brighter than their TCF analogues.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 16
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31319662
- Full Text :
- https://doi.org/10.1021/acs.joc.9b01120