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3,6-Disubstituted carbazole-based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid


Reference:

Han, F., Chi, L., Liang, X., Ji, S., Liu, S., Zhou, F., Wu, Y., Han, K., Zhao, J. and James, T. D., 2009. 3,6-Disubstituted carbazole-based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid. Journal of Organic Chemistry, 74 (3), pp. 1333-1336.

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Official URL:

http://dx.doi.org/10.1021/jo8025669

Abstract

Carbazole-based bisboronic acids were found to be enanti-oselective fluorescent sensors for tartaric acid. The fluorescence response toward the enantiomers of tartaric acid at neutral pH displayed enhancement/diminishment. The sensor displays an unusual fluorescence intensity-pH relationship with diminished emission at acidic pH but enhanced emission at basic pH. Photoinduced electron transfer (PET) from the fluorophore to the protonated amine/phenylboronic acid unit is proposed to be responsible for this effect, which is rationalized by density functional theory (DFT) calculations.

Details

Item Type Articles
CreatorsHan, F., Chi, L., Liang, X., Ji, S., Liu, S., Zhou, F., Wu, Y., Han, K., Zhao, J. and James, T. D.
DOI10.1021/jo8025669
Uncontrolled Keywordselectron transitions, fluorescence, sensors, acids, density functional theory
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code14768

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