title: Synthesis of ethynylated phenothiazine based fluorescent boronic acid probes.
abstract: Ethynylated phenothiazine based fluorescent boronic acid probes were prepared. Sonogashira coupling reaction was used to introduce substituted phenylethynylene fragments to the phenothiazine fluorophore to extend the π-conjugation and to enhance the emission property. The photophysical properties and the binding properties of these probes with hydroxyl acids were investigated. We found that the probes with significant ICT effect show emissions which are sensitive to solvent polarity. The phenothiazine moiety is proved to be electron-donating. We found the substitution profile imparts significant effect on the photophysical properties of the probes. For example, one of the probes shows d-PeT effect, whereas the regioisomer probe with similar π-conjugation fragment but different substitution profile shows the a-PeT effect. The easy derivatization of phenothiazine fluorophore, the structure-photophysical property relation and the novel d-PeT fluorescence transduction profile of the phenothiazine based probes described herein may inspire more investigation into this fascinating research area.
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, People's Republic of China.
authors.forename: Yubo
authors.initials: Y
authors.lastname: Wu
authors.forename: Huimin
authors.initials: H
authors.lastname: Guo
authors.forename: Jingyin
authors.initials: J
authors.lastname: Shao
authors.forename: Xin
authors.initials: X
authors.lastname: Zhang
authors.forename: Shaomin
authors.initials: S
authors.lastname: Ji
authors.forename: Jianzhang
authors.initials: J
authors.lastname: Zhao
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001897:Boronic Acids / Q000032:analysis*; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D015336:Molecular Probe Techniques; D010640:Phenothiazines / Q000737:chemistry*; D012997:Solvents
chemical_list: D000480:Alkynes; D001897:Boronic Acids; D005456:Fluorescent Dyes; D010640:Phenothiazines; D012997:Solvents; C031637:phenothiazine