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Reductive cleavage of CC bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S†
Chemical Science ( IF 7.6 ) Pub Date : 2018-09-11 00:00:00 , DOI: 10.1039/c8sc03430c
Chunfei Wang 1 , Xiaoxiang Cheng 1 , Jingyun Tan 1 , Zhaoyang Ding 1 , Wenjing Wang 2 , Daqiang Yuan 2 , Gang Li 1 , Hongjie Zhang 1 , Xuanjun Zhang 1
Affiliation  

Reductive cleavage of alkenes is rarely reported in synthetic chemistry. Here we report a unique H2S-mediated reductive cleavage of C[double bond, length as m-dash]C bonds under mild conditions, which is a successful new strategy for the design of probes for effective sensing of H2S with turn-on dual-color fluorescence. A short series of phenothiazine ethylidene malononitrile derivatives were shown to react with H2S, via reductive cleavage of C[double bond, length as m-dash]C bonds with intramolecular cyclization reactions to form thiophene rings. Enlightened by this new reaction mechanism, four effective probes with turn-off to turn-on fluorescence switches were successfully applied for sensing H2S, an important gaseous signalling molecule in living systems, among which PTZ-P4 exhibited two fluorescent colors after reductive cleavage. The dual-color probe was applied for imaging endogenous H2S and showed distinct differences in brightness in living C. elegans for wild type N2, glp-1 (e2144) mutants (higher levels of endogenous H2S), and cth-1 (ok3319) mutants (lower levels of endogenous H2S). The discovery of H2S-mediated reductive cleavage of C[double bond, length as m-dash]C bonds is expected to be valuable for chemical synthesis, theoretical studies, and the design of new fluorescent H2S probes.

中文翻译:

CC 键的还原裂解作为开启双荧光有效检测 H2S 的新策略†

在合成化学中很少报道烯烃的还原裂解。在这里,我们报告了在温和条件下独特的 H 2 S 介导的 C [双键,长度为 m-dash]C 键还原切割,这是一种成功的新策略,可用于设计有效检测具有开启双色荧光的 H 2 S 的探针。一小部分吩噻嗪亚乙基丙二腈衍生物显示出与 H 2 S 反应,通过C C 键的还原裂解[双键,长度为 m-dash]和分子内环化反应形成噻吩环。在这种新反应机制的启发下,四种具有关闭到打开荧光开关的有效探针成功应用于感测H 2S是生命系统中重要的气态信号分子,其中PTZ-P4在还原裂解后呈现出两种荧光颜色。双色探针应用于内源性 H 2 S 成像,并显示出活的秀丽隐杆线虫野生型 N2、glp-1 ( e2144 ) 突变体(更高水平的内源性 H 2 S)和cth -1的亮度差异( ok3319 ) 突变体(较低水平的内源 H 2 S)。H 2 S 介导的 C [双键,长度为 m-dash]C 键还原断裂的发现有望对化学合成、理论研究和新型荧光 H 2的设计具有重要意义S 探头。
更新日期:2018-09-11
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