Enantioselective fluorescent sensors for amino acid derivatives based on BINOL bearing benzoyl unit

The derivatives of BINOL, (S)-1 and (R)-1, and their analogues have been prepared and the structures of these compounds have been characterized by IR, MS, 1H, and 13C NMR spectroscopy and elemental analysis. The enantioselective recognition of these receptors has been studied by fluorescence titration and 1H NMR spectroscopy. The receptors exhibited different chiral recognition abilities toward some enantiomers of chiral materials and formed 1:1 complexes between host and guest. Receptor (S)-1 or (R)-1 exhibits excellent enantioselective fluorescent recognition abilities toward amino acid derivatives.

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C34H22O4(S)-3,3′-Bis-benzoyl-2,2′-bis-dihydroxy-1,1′-binaphthyl[α]D20=-94.2 (c 1.00, CHCl3)Absolute configuration: (S)Source of chirality: (S)-1,1′-bi-2-naphthol

C36H26O4(S)-3,3′-Bis-benzoyl-2,2′-dimethoxy-1,1′-binaphthyl[α]D20=-93.6 (c 1.00, CHCl3)Absolute configuration: (S)Source of chirality: (S)-1,1′-bi-2-naphthol