Issue 44, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Aug 2018
Accepted
10 Sep 2018
First published
11 Sep 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 8369-8374

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, 9, 8369 DOI: 10.1039/C8SC03430C

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