Enantioselective fluorescent recognition of chiral acids by 3- and 3,3′-aminomethyl substituted BINOLs |
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Authors: | Jing Lin |
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Institution: | Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319, USA |
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Abstract: | Benzylaminomethyl groups are introduced to the 3,3′-positions of BINOL. The resulting compounds can be used to conduct the enantioselective fluorescent recognition of mandelic acid and N-benzyloxycarbonylphenylglycine. In the presence of (S)-mandelic acid, compound (R)-2 showed over 30-fold fluorescence enhancement with the ef ef=enantiomeric fluorescence difference ratio=(IS−I0)/(IR−I0)] up to 4.2. In the presence of d-N-benzyloxycarbonylphenylglycine, compound (RR)-4 showed up to 15-fold fluorescence enhancement with the ef up to 5.0. These high fluorescence sensitivity and enantioselectivity make compounds (R)-2 and (RR)-4 practically useful sensors for the recognition of the chiral acids in apolar solvents. |
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Keywords: | Enantioselective Fluorescent sensors Mandelic acid Amino acids BINOL |
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