The first near IR fluorescent probe for the chemoselective and enantioselective recognition of arginine in aqueous solution is reported in this work. This probe, made of a 1,1’‐binaphthyl‐based chiral aldehyde unit and a rhodamine‐based near IR chromophore, in combination with La3+exhibits highly chemoselective as well as enantioselective fluorescent enhancement with arginine at λ=764 nm upon excitation at λ=690 nm. Little or no fluorescent response is observed toward the chirality miss‐matched arginine enantiomer or other common amino acids and their enantiomers. This probe also allows visual discrimination of the arginine enantiomers because of its fast and distinct color change upon interaction with the substrate.
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Abstract -
Abstract A novel
C 3symmetric 1,1’‐bi‐2‐naphthol‐based Schiff base (R ,R ,R )‐6 has been synthesized which shows highly selective fluorescence enhancement with Zn2+among 21 metal cations examined. Its sensitivity and selectivity are found to be greater than other relatedC 2(1 ) andC 1[(R )‐9 ] symmetric compounds in the fluorescent recognition of Zn2+. The mechanistic study reveals that the selective fluorescence enhancement of the probe can be attributed to the formation of a unimolecular multidentate 6‐coordinated Zn2+complex. -
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