Development of an indole-based boron-dipyrromethene fluorescent probe for benzenethiols.
Development of an indole-based boron-dipyrromethene fluorescent probe for benzenethiols.
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DOI：
10.1021/jp109845g
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发表时间：
2011-02
期刊：
影响因子：
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通讯作者：
Chunchang Zhao;Yu Zhou;Qiuning Lin;Linyong Zhu;Peng Feng;Yulin Zhang;Jian Cao
中科院分区：
文献类型：
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作者：
Chunchang Zhao;Yu Zhou;Qiuning Lin;Linyong Zhu;Peng Feng;Yulin Zhang;Jian Cao
化学上相关的苯硫酚和脂肪族硫醇之间的区别是一个大问题。本文以吲哚类化合物Bodipy为荧光团，以2，4-二硝基苯磺酰基为识别单元，构建了一种荧光探针Bodipy-1，实现了两者之间的选择性。所制备的探针中的Bodipy基团通过来自苯硫酚的硫醇阴离子的芳香亲核取代选择性地释放，导致在缓冲溶液中的发射光谱中的蓝-红切换;即，在发射光谱中出现两个新的峰Bodipy-2的苯酚/苯酚盐状态在565和629 nm处。通过改变pH值从6.6到8.8，I（565）/I（629）的强度比在完全转化为Bodipy-2后从2.0变化到0.3，约为1.5。7-倍发射率变化。这种通过改变pH值的比率发射特性使得Bodipy-1成为通过仔细选择反应pH来区分苯硫酚与脂肪族硫醇的有前途的探针。
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-red 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 I(565)/I(629) 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.