Benzothiazole-Derived Sulfones and Sulfoxides as Reactive Templates for Biothiols and Sulfane Sulfurs

In this work we studied the reactions of benzothiazole sulfones and sulfoxides toward reactive sulfur species. The reaction of thiols with benzothiazole sulfones produces sulfinic acids (RSO2H), which can further react with sulfane sulfurs to form thiosulfonic acids (RSO2SH). This was used to design fluorescent sensors for hydrogen polysulfides. The reaction of thiols with benzothiazole sulfoxides produces sulfenic acids (RSOH), which can undergo fast intramolecular cyclization and be used to design thiol-triggered fluorescent sensors.

Automated summary

In this study, we investigated the reactions of benzothiazole sulfones and sulfoxides with reactive sulfur species. The reaction between thiols and benzothiazole sulfones yielded sulfinic and thiosulfonic acids, which were utilized to develop fluorescent sensors for hydrogen polysulfides. The reaction of thiols with benzothiazole sulfoxides resulted in sulfenic acids, which could undergo intramolecular cyclization and were employed to design thiol-triggered fluorescent sensors.