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4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for NIR-Emitting Push–Pull Dipolar Fluorophores
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-07-19 00:00:00 , DOI: 10.1021/acs.joc.9b01120 Maxime Rémond 1 , Zheng Zheng 1 , Erwann Jeanneau 2 , Chantal Andraud 1 , Yann Bretonnière 1 , Sébastien Redon 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-07-19 00:00:00 , DOI: 10.1021/acs.joc.9b01120 Maxime Rémond 1 , Zheng Zheng 1 , Erwann Jeanneau 2 , Chantal Andraud 1 , Yann Bretonnière 1 , Sébastien Redon 1
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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.
中文翻译：
4,5,5-三甲基-2,5-二氢呋喃基电子吸电子基团的近红外发射推挽偶极荧光团。
在推挽偶极染料的分子工程学背景下，我们介绍了著名的电子接受基团2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran（TCF）。（苯并[ d ]噻唑-2-基）部分的引入失败，并且获得了意外的结构。另一方面，苯硫基和苯磺酰基实体已成功地引入到2-（二氰基亚甲基）-2,5-二氢呋喃环的3位，从而可以接触到新的电子受体基团和在溶液或溶液中显示近红外发射的偶极荧光团。固态，比其TCF类似物亮。
更新日期：2019-07-19
中文翻译：
4,5,5-三甲基-2,5-二氢呋喃基电子吸电子基团的近红外发射推挽偶极荧光团。
在推挽偶极染料的分子工程学背景下，我们介绍了著名的电子接受基团2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran（TCF）。（苯并[ d ]噻唑-2-基）部分的引入失败，并且获得了意外的结构。另一方面，苯硫基和苯磺酰基实体已成功地引入到2-（二氰基亚甲基）-2,5-二氢呋喃环的3位，从而可以接触到新的电子受体基团和在溶液或溶液中显示近红外发射的偶极荧光团。固态，比其TCF类似物亮。
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