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4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for NIR-Emitting Push–Pull Dipolar Fluorophores
- Rémond, Maxime, Zheng, Zheng, Jeanneau, Erwann, Andraud, Chantal, Bretonnière, Yann, Redon, Sébastien
- Journal of organic chemistry 2019 v.84 no.16 pp. 9965-9974
- chemical reactions, engineering, fluorescent dyes, moieties, organic chemistry, organic compounds
- 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.