Synthesis and enantioselective fluorescent sensors for amino acid derivatives based on BINOL

Abstract

Four novel derivatives of 1,1′-bi-2-naphthol have been prepared and the structures of these compounds characterised by IR, MS, ¹H and ¹³C NMR spectroscopy and elemental analysis. The enantioselective recognition of these sensors has been studied by fluorescence titration and ¹H NMR spectroscopy. The sensors exhibited different chiral recognition abilities towards N-Boc-protected amino acid anions and formed 1:1 complexes between the host and the guest. Sensors exhibit excellent enantioselective fluorescent recognition ability towards the amino acid derivatives.

Keywords:

• anions
• fluorescence sensor
• enantioselective recognition
• NMR spectroscopy

Acknowledgements

We thank the National Natural Science Foundation of China (Grant No. 20872027/B0206) and the Education Department of Henan Province of China (2010B150004) for financial support.