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.
Original language | English |
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Pages (from-to) | 1333-1336 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 3 |
Early online date | 14 Jan 2009 |
DOIs | |
Publication status | Published - 6 Feb 2009 |
Keywords
- Electron transitions
- Fluorescence
- Sensors
- Acids
- Density functional theory