Highly selective fluorescent recognition of amino alcohol based on chiral calix[4]arenes bearing L-tryptophan unit

Abstract

Four two-armed chiral calix[4]arenes (1a–1d) functionalised at the lower ring with amino acid units have been synthesised and the structures of these compounds were characterised by IR, MS, ¹H NMR, ¹³C NMR spectra and elemental analysis. Their molecular recognition abilities towards amino alcohol were examined by fluorescence titration experiment in three kinds of solution. The results indicated that these receptors exhibited excellent fluorescent response to phenylglycinol and could distinguish phenylglycinol from phenylalaninol rapidly through the obvious difference in the fluorescent response. Solvent comparative experiments also indicated that acetonitrile was the best solvent to detect these phenomena.

Keywords:

• calix[4]arene
• molecular recognition
• fluorescence
• amino alcohol

Acknowledgements

We thank the National Natural Science Foundation for financial support (Grant No. 20572080).