关键词: 手性, 自具微孔聚合物, 手性识别, 荧光识别, 苯丙氨酸

Chirality, a ubiquitous phenomenon in nature, profoundly influences material properties. The precise synthesis of chiral compounds and enantiomer recognition techniques hold promise as pivotal advancements in the realms of medicine, informatics, and materials science, yet remain a formidable challenge. In this paper, we prepared a monochiral self-forming microporous polymers ((R)-HSBI-Is) through direct-synthesis method, and applied it for chiral recognition of phenylalanine. First, commencing with bisphenol A, racematic 3,3,3',3'-tetramethyl-1,1'-spirodine-7,7'-diol (6,6'-TMSOL) was synthesized, and form transitional complex derivates through adding chiral reagents (L-menthyl chloroformate). After three times recrystallization under －18 ℃, the diastereoisomers of the complex derivates were successfully separated due to their different solubility. After hydrolysis reaction, the auxiliary groups were removed and chiral monomer was synthesized. This study achieved the artful synthesis of pure (R)-3,3,3',3'-tetramethyl-1,1'-spirodine-7,7'-diol ((R)-6,6'-TMSOL). Subsequently, chiral polymer of intrinsic microporosity ((R)-HSBI-Is) were crafted through Friedel-Crafts reaction with isatin molecules. And we delved the mechanism of synthesizing chiral polymers. These polymers were comprehensively evaluated using techniques such as nuclear magnetic resonance, infrared spectroscopy, UV spectroscopy, specific surface area and pore size analysis, and thermogravimetric analysis. Our findings reveal that the polymer boasts a high specific surface area and robust fluorescence. It also shows a great performance in thermal stability. The fluorescence experiments on chiral molecules (phenylalanine, tryptophan, 1,1'-binaphthyl-2,2'-diol (BINOL), 1,1'-spirobiindane (SPINOL) and 1-phenylethanol) were carried out to testify the recognition performance of chiral polymer. The results proved that the polymer exhibits a remarkable selective fluorescence enhancement towards L-phenylalanine. Specifically, the L- and D-configuration selectivity achieved is 34.9, positioning it as an exceptional chiral recognition agent for L-phenylalanine.

Key words: chirality, polymers of intrinsic microporosity, chiral recognition, fluorescence recognition, phenylalanine