The detection of metal ions and amino acids by the aniline oligomer-based receptor has not been reported yet, to the best of our knowledge. In this study, an efficient multifunctional cation-amino acid sensor (CAS) with aniline moiety and chiral thiourea binding site was synthesized by the reaction of aniline trimer and (S)-(+)-1-phenyl ethyl isothiocyanate. CAS can sense Fe, Cu, Ag ions, and L-tryptophan. These results can be recognized by the naked eye. The appropriate pH range for the quantitative analysis of Fe, Cu and Ag by CAS in DMSO/water (30 vol% water) was evaluated. The interaction between CCS and metal ions was analyzed by H NMR titration. The detection limits of CAS for the Cu, Ag and Fe were 0.214, 0.099, and 0.147 μM, respectively. Moreover, the CASCu complex can act as a turn-on fluorescence sensor for L-tryptophan. On the contrary, there is no response upon the addition of other amino acids, such as L-histidine, L-proline, L-phenylalanine, L-threonine, L-methionine, L-tyrosine, and L-cystine to CASCu complex.
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