4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for NIR-Emitting Push–Pull Dipolar Fluorophores - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2019

4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for NIR-Emitting Push–Pull Dipolar Fluorophores

Zheng Zheng
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Erwann Jeanneau
Yann Bretonnière
Sébastien Redon

Résumé

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-(dicyanomethy-lidene)-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.
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Dates et versions

hal-02319337 , version 1 (17-10-2019)

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Maxime Remond, Zheng Zheng, Erwann Jeanneau, Chantal Andraud, Yann Bretonnière, et al.. 4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for NIR-Emitting Push–Pull Dipolar Fluorophores. Journal of Organic Chemistry, 2019, 84 (16), pp.9965-9974. ⟨10.1021/acs.joc.9b01120⟩. ⟨hal-02319337⟩
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