Enantioselective recognition of tartaric acids with ethynylated carbazole-based chiral bisboronic acid chemosensors with improved response at acidic pH

J Fluoresc. 2011 Sep;21(5):1979-86. doi: 10.1007/s10895-011-0898-z. Epub 2011 May 19.

Abstract

Chiral bisboronic acid chemosensors based on ethynylated carbazole were prepared. The chiral chemosensors show red-shifted emission than the chemosensors with unsubstituted carbazole fluorophore. a-PET effect was found for the chemosensors, which is different from our previous observation of the d-PET effect for boronic acid chemosensors based on carbazole. Enantioselective recognition of tartaric acids was implicated with these chemosensors. Consecutive fluorescence emission enhancement/diminishment were observed with increasing the concentration of the tartaric acids, which is tentatively assigned to the transition of the binding stoichiometry from 1:1 binding to 1:2 binding. In particularly interesting is the improved fluorescence response at acidic pH for recognition of tartaric acids, which is rarely observed for a-PET chemosensors. We propose that the sensing is due to hybrid mechanism of a-PET/d-PET and conformational restriction upon binding. Our results will be useful for design of chiral boronic acid chemosensors with improved fluorescence response at acidic pH, which are rarely reported.

MeSH terms

  • Boronic Acids / chemistry*
  • Carbazoles / chemistry*
  • Fluorescent Dyes / chemistry*
  • Hydrogen-Ion Concentration
  • Stereoisomerism
  • Tartrates / chemistry*

Substances

  • Boronic Acids
  • Carbazoles
  • Fluorescent Dyes
  • Tartrates
  • carbazole
  • tartaric acid