Development of an Indole-Based Boron-Dipyrromethene Fluorescent Probe for Benzenethiols

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• 作者：Chunchang Zhao ; Yu Zhou ; Qiuning Lin ; Linyong Zhu ; Peng Feng ; Yulin Zhang ; Jian Cao
• 刊名：Journal of Physical Chemistry B
• 出版年：2011
• 出版时间：February 3, 2011
• 年：2011
• 卷：115
• 期：4
• 页码：642-647
• 全文大小：348K
• 年卷期：v.115,no.4(February 3, 2011)
• ISSN：1520-5207

文摘

Discrimination between chemically related benzenethiols and aliphatic thiols represents a big problem. In this paper, a fluorescent probe, Bodipy-1, containing an indole-based Bodipy as a fluorophore and a 2,4-dinitrobenzenesulfonyl group as a recognition unit was constructed to achieve the selectivity between them. The Bodipy group in the prepared probe was selectively released through aromatic nucleophilic substitution by thiolate anions from benzenethiols, resulting in blue鈭抮ed switching in the emission spectra in buffer solutions; that is, two new peaks of the phenol/phenolate state of Bodipy-2 at 565 and 629 nm appeared in emission spectra. By varying the pH value from 6.6 to 8.8, the intensity ratio of I₅₆₅/I₆₂₉ varies from 2.0 to 0.3 after complete conversion to Bodipy-2, a ca. 7-fold emission ratio change. This ratiometric emission property by varying the pH value makes Bodipy-1 a promising probe to discriminate benzenethiols from aliphatic thiols by careful selection of the reaction pH.