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Reductive cleavage of C[double bond, length as m-dash]C bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S

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Abstract

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.

Graphical abstract: Reductive cleavage of C [[double bond, length as m-dash]] C bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S

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Publication details

The article was received on 02 Aug 2018, accepted on 10 Sep 2018 and first published on 11 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC03430C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Reductive cleavage of C[double bond, length as m-dash]C bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S

    C. Wang, X. Cheng, J. Tan, Z. Ding, W. Wang, D. Yuan, G. Li, H. Zhang and X. Zhang, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC03430C

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