pH-Dependent Si-Fluorescein Hypochlorous Acid Fluorescent Probe: Spirocycle Ring-Opening and Excess Hypochlorous Acid-Induced Chlorination

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• 作者：Quinn A. Best ; Narsimha Sattenapally ; Daniel J. Dyer ; Colleen N. Scott ; Matthew E. McCarroll
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：September 11, 2013
• 年：2013
• 卷：135
• 期：36
• 页码：13365-13370
• 全文大小：458K
• 年卷期：v.135,no.36(September 11, 2013)
• ISSN：1520-5126

文摘

We report the synthesis and characterization of a fluorescent probe (Hypo-SiF) designed for the detection of hypochlorous acid (HOCl) using a silicon analogue of fluorescein (SiF). The probe is regulated in an 鈥渙ff鈥搊n鈥?fashion by a highly selective thioether spirocyclic nonfluorescent structure that opens to form a mixture of fluorescent products in the presence of HOCl. Over a range of pH values, the probe reacts with a stoichiometric amount of HOCl, resulting in a mixture of two pH-dependent fluorescent species, a SiF disulfide product and a SiF sulfonate product. The unique colorimetric properties of the individual SiF fluorophores were utilized to perform simultaneous detection of HOCl and pH. When an excess of HOCl is present, the SiF fluorophores become chlorinated, via an intermediate halohydrin, resulting in a more pH independent and red-shifted fluorophore.