3,6-Disubstituted carbazole-based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid.
| Autor: | Han F; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, 158 Zhongshan Road, Dalian 116012, People's Republic of China., Chi L, Liang X, Ji S, Liu S, Zhou F, Wu Y, Han K, Zhao J, James TD |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2009 Feb 06; Vol. 74 (3), pp. 1333-6. |
| DOI: | 10.1021/jo8025669 |
| Abstrakt: | Carbazole-based bisboronic acids were found to be enantioselective 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. |
| Databáze: | MEDLINE |
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