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Reductive cleavage of C═C bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S
Wang C.1; Cheng X.1; Tan J.1; Ding Z.1; Wang W.2; Yuan D.2; Li G.1; Zhang H.1; Zhang X.1
2018
Source PublicationChemical Science
ISSN20416539 20416520
Volume9Issue:44Pages:8369-8374
Abstract

Reductive cleavage of alkenes is rarely reported in synthetic chemistry. Here we report a unique HS-mediated reductive cleavage of C═C bonds under mild conditions, which is a successful new strategy for the design of probes for effective sensing of HS with turn-on dual-color fluorescence. A short series of phenothiazine ethylidene malononitrile derivatives were shown to react with HS, via reductive cleavage of C═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 HS, 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 HS and showed distinct differences in brightness in living C. elegans for wild type N2, glp-1 (e2144) mutants (higher levels of endogenous HS), and cth-1 (ok3319) mutants (lower levels of endogenous HS). The discovery of HS-mediated reductive cleavage of C═C bonds is expected to be valuable for chemical synthesis, theoretical studies, and the design of new fluorescent HS probes.

DOI10.1039/c8sc03430c
URLView the original
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000450436100004
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Cited Times [WOS]:6   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionFaculty of Health Sciences
Affiliation1.Universidade de Macau
2.State Key Laboratory of Structural Chemistry, Fuzhou
Recommended Citation
GB/T 7714
Wang C.,Cheng X.,Tan J.,et al. Reductive cleavage of C═C bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S[J]. Chemical Science,2018,9(44):8369-8374.
APA Wang C..,Cheng X..,Tan J..,Ding Z..,Wang W..,...&Zhang X..(2018).Reductive cleavage of C═C bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S.Chemical Science,9(44),8369-8374.
MLA Wang C.,et al."Reductive cleavage of C═C bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S".Chemical Science 9.44(2018):8369-8374.
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