Furo-Fused BINOL Based Crown as a Fluorescent Chiral Sensor for Enantioselective Recognition of Phenylethylamine and Ethyl Ester of Valine

Abstract

A furo-fused BINOL based chiral crown was developed as an enantioselective chiral sensor for phenylethylamine and ethyl ester of valine. Fusion of furan to BINOL has resulted in a highly stereo-discriminating backbone for the chiral crown developed. This chiral crown exhibited a fluorescence enhancement difference of 2.97 times between two enantiomers of phenylethylamine and 2.55 times between two enantiomers of ethyl ester of valine. The ratio of association constants for two diastereomeric complexes of two enantiomers of phenylethylamine was found to be 11.30, and the ratio for two enantiomers of ethyl ester of valine was 7.02.

Synthesis and optical characterization of novel azacrown ethers containing an acridinone or an N-methylacridinone unit as potential fluorescent chemosensors

“…In the past two decades many efforts have been devoted to the development of fluorescent chiral chemosensors, 47 among them crown ether based ones containing various fluorescent units. [48][49][50][51][52][53] One of them containing an optically active binaphthyl unit incorporated into the crown ether framework, and having a PET type modular structure, showed a moderate selectivity for the enantiomers of 2-phenylglycinol. 53 Chiral ligands are usually designed and tested for enantiomeric recognition of chiral analytes such as amino acid derivatives, amino alcohols and primary amines.…”

Recent progress on using BINOLs in enantioselective molecular recognition

“…The furo-fused BINOL crown ether (R)-40 is thus prepared, which exhibits moderate enantioselectivity for phenylethylamine and ethyl ester of valine. 58 As mentioned earlier, the 3,3 0 -BINOL-based boronic ester (S)-16 shows enantioselective fluorescent quenching with phenylglycinol. The 3,3 0 -substitutions are expected to have very little effect on the dihedral angle between the two naphthalene rings.…”

Chiral Heterocycle-Based Receptors for Enantioselective Recognition

“…The present review article presents a detailed account of the recent developments in the design and synthesis of various chiral receptors with heterocyclic motif such as pyridine [18], chromene [32,33], imidazole [34], benzimidazole [35,36], furan [37], thiophene [38], oxazole [22][23][24][25] etc. and its application in the enantioselective recognition of different classes of chiral analytes [39,40].…”