title: Development of an indole-based boron-dipyrromethene fluorescent probe for benzenethiols.
abstract: 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.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science & Technology, Shanghai 200237, People's Republic of China. zhaocchang@ecust.edu.cn
authors.forename: Chunchang
authors.initials: C
authors.lastname: Zhao
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhou
authors.forename: Qiuning
authors.initials: Q
authors.lastname: Lin
authors.forename: Linyong
authors.initials: L
authors.lastname: Zhu
authors.forename: Peng
authors.initials: P
authors.lastname: Feng
authors.forename: Yulin
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jian
authors.initials: J
authors.lastname: Cao
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002021:Buffers; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000032:analysis*; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013438:Sulfhydryl Compounds / Q000032:analysis*
chemical_list: D001896:Boron Compounds; D002021:Buffers; D005456:Fluorescent Dyes; D007211:Indoles; D010636:Phenols; D013438:Sulfhydryl Compounds; C507544:dipyrromethene; D011162:Porphobilinogen; C042983:thiophenol; C030374:indole