A chiral (S)-BINOL based fluorescent sensor for the recognition of Fe(III) and cascade discrimination of α-amino acids

Minor groove thiosemicarbazone functionalized (S)-BINOL 1 has been synthesized starting from (S)-BINOL; these new thiosemicarbazone functionalized (S)-BINOL molecules introduce new opportunities in the field of chiral recognition and Fe(III) sensing. The developed sensor can serve as a turn off sensor for Fe(III) with high selectivity among metal ions tested. The in situ generated Fe(III) complex of 1 exhibit remarkable fluorescent chiral discrimination toward unmodified α-amino acids via a ligand displacement mechanism.

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2,2′-((2,2′-dihydroxy-[1,1′-binaphthalene]-3,3′-diyl)bis(methanylylidene))bis(hydrazinecarbothioamide)C24H20N6O2S2[α]D25 = +230.0 (c 0.8, CH2Cl2)Absolute configuration: (S)Source of chirality: (S)-BINOL