Journal
JOURNAL OF FLUORESCENCE
Volume 21, Issue 3, Pages 1143-1154Publisher
SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s10895-010-0791-1
Keywords
Boronic acid; Fluorescent chemosensors; d-PeT; Phenothiazine
Funding
- NSFC [20972024, 21073028]
- Fundamental Research Funds for the Central Universities [DUT10ZD212]
- Ministry of Education [SRFDP-200801410004, NCET-08-0077]
- Royal Society (UK)
- NSFC (China-UK Cost-Share Science Networks) [21011130154]
- State Key Laboratory of Chemo/Biosensing and Chemometrics [2008009]
- Education Department of Liaoning Province [2009 T015]
- State Key Laboratory of Fine Chemicals [KF0802]
- Dalian University of Technology
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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 pi-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 pi-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.
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