Selective Identification of Phenylalanine Using Cucurbit[7,8]uril-Based Fluorescent Probes

Abstract

The interactions of two host–guest inclusion complexes comprised of cucurbit[7]uril (Q[7]) and cucurbit[8]uril (Q[8]) with a derivative of toluidine blue O (TB) have been investigated using 1H NMR and fluorescence spectroscopy. The experimental results revealed that the Q[7] host interacts with a TB molecule to form a 1:1 inclusion complex and the Q[8] host interacts with two TB guest molecules to form a 1:2 inclusion complex. The inclusion of the TB guest molecule within the Q[7] host gave rise to significant fluorescence enhancement, whereas the inclusion of the TB guest molecule within the Q[8] host resulted in significant fluorescence quenching. Further recognition experiments involving a series of l-α-amino acids revealed that the TB@Q[7] inclusion fluorescence probe exhibits high selectivity for the recognition of phenylalanine via significant fluorescence quenching in an aqueous solution, whereas the TB@Q[8] inclusion fluorescence probe also exhibited high selectivity for phenylalanine recognition via fluorescence enhancement in an aqueous solution.