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Trapping Hydrogen Sulfide (H2S) with Diselenides: The Application in the Design of Fluorescent Probes

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2015

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American Chemical Society
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Peng, Bo, Caihong Zhang, Eizo Marutani, Armando Pacheco, Wei Chen, Fumito Ichinose, and Ming Xian. 2015. “Trapping Hydrogen Sulfide (H2S) with Diselenides: The Application in the Design of Fluorescent Probes.” Organic Letters 17 (6): 1541-1544. doi:10.1021/acs.orglett.5b00431. http://dx.doi.org/10.1021/acs.orglett.5b00431.

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Here we report a unique reaction between phenyl diselenide-ester substrates and H2S to form 1,2-benzothiaselenol-3-one. This reaction proceeded rapidly under mild conditions. Thiols could also react with the diselenide substrates. However, the resulted S–Se intermediate retained high reactivity toward H2S and eventually led to the same cyclized product 1,2-benzothiaselenol-3-one. Based on this reaction two fluorescent probes were developed and showed high selectivity and sensitivity for H2S. The presence of thiols was found not to interfere with the detection process.

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