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Synthesis and Evaluation of an Imidazo-Benzocrown Ether Functionalised Amino Acid as a new Fluorimetric Chemosensor for Metal Ion Detection
Published: 31 October 2013 by MDPI in The 17th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic, Medicinal and Natural Products
Abstract: The field of fluorescent chemosensors has grown in recent years due to their importance in applications such as in material sciences, biomedical, analytical chemistry and environmental sciences. Following our research interests that include the synthesis and application of fluorimetric chemosensors for anions and cations based on heterocycles and amino acids, a new imidazo-benzocrown ether functionalised amino acid 3 was synthesized in 70% yield by condensation of functionalised phenylalanine 1 with 4-amino-5-nitrobenzo-15-crown-5-ether 2 in the presence of Na2S2O4 in DMSO. Compound 3 was studied by fluorescence spectroscopy in the presence of increasing amount of metal ions such as Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, Hg2+, Na+, Ni2+, Pd2+ and Zn2+. The metal cation sensing properties displayed by 3 showed that it is a promising candidate for sensory applications.
Keywords: Phenylalanine; Benzimidazole; Fluorescence; optical chemosensors: Crown ether; cation sensing