Selective recognition of tryptophan by a methylpillar[5]arene-based supramolecular fuorescent probe

Herein we present a simple fluorescence quenching method to selectively recognise and determine L-tryptophan (L-Trp) out of other 19 natural amino acids. Methylpillar[5]arene (MeP5), which is employed as a macrocyclic fluorescent probe, exhibits fluorescence activity in the solution of poor solvents because of aggregation-induced emission (AIE) effect. Fluorescence quenching of MeP5 in the solution of EtOH/CH₂Cl₂ (98/2, v/v) was observed upon the addition of L-Trp whereas other 19 natural amino acids did not bring about obvious change in fluorescence intensity. ¹H NMR titration, fluorescence spectroscopy, mass spectrometry and theoretical analysis revealed that L-Trp can be encapsulated into the cavity of MeP5 to form a stable 1:1 host-guest inclusion complex which accounts for the quenching characteristics. The proposed procedure in this investigation offers an attractive and promising method for the selective detection of L-Trp in a mixture of natural amino acids.