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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.

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.

SUBMITTER: Wang C

PROVIDER: S-EPMC6247518 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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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.

Wang Chunfei C Cheng Xiaoxiang X Tan Jingyun J Ding Zhaoyang Z Wang Wenjing W Yuan Daqiang D Li Gang G Zhang Hongjie H Zhang Xuanjun X

Chemical science 20180911 44

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 ...[more]

PMID: 30542584

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Project description:In a natural environment, Fe(ii) adsorbed onto the surfaces of natural particles to form various surface complex species can influence the transformation of contaminants. The reductive reactivity of the [[triple bond, length as m-dash]Fe(iii)]/[[triple bond, length as m-dash]Fe(ii)] couples are close correlated with the surrounding conditions. In this study, we investigated the effects of Si(iv) on the reductive reactivity of [[triple bond, length as m-dash]Fe(iii)]/[[triple bond, length as m-dash]Fe(ii)] couples adsorbed onto γ-Al2O3. Experiments were conducted under different conditions to investigate the effects of Si(iv) on the reactivity of [[triple bond, length as m-dash]Fe(iii)]/[[triple bond, length as m-dash]Fe(ii)] couples for 2-nitrophenol (2-NP, selected as the model pollutant) reduction in γ-Al2O3 suspensions. Kinetics results revealed that chemical adsorption is the rate limiting step in Fe(ii) and Si(iv) adsorption processes and the reduction of 2-NP is an endothermic reaction. The linear correlations between the reduced peak oxidation potential (E p) (versus SCE) and 2-NP reduction rate (ln k), and between the adsorbed Fe(ii) density (ρ Fe(II)) and ln k, illustrated that E p and ρ Fe(II) are two key factors in the inhibiting effects of Si(iv) on the reductive reactivity of Fe(iii)/Fe(ii) couples on γ-Al2O3. The results of Fe K-edge X-ray absorption spectroscopy revealed that the increase of Si(iv) concentration resulted in the gradual change in the composition of the adsorbed Fe species from pure [triple bond, length as m-dash]AlOFe+ (γ-Al2O3 surface-bound Fe(ii) species with higher reductive reactivity) to a mixture of [triple bond, length as m-dash]AlOFe+ and [triple bond, length as m-dash]SiOFe+ (SiO2 surface-bound Fe(ii) species with lower reductive reactivity), leading to the decrease in ρ Fe(II), the positive shift in E p, the increase in activation energy (E a), and consequently the decrease in the reduction rate (ln k) of 2-NP.

Dataset Information

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.

Publications

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 H<sub>2</sub>S.

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