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 regents (L-menthyl choroformate). After three times recrystallization under -18 ℃,complex derivates were split due to their different solubility, and acquire corresponding complex derivate. 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 Fourier reaction with indigo 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. Finally, possible reasons for high fluorescence enhancement effect of L-phenylalanine were presented: this might be the result of the simultaneous effect of suitable pores and functional groups, and a complex was formed between L-phenylalanine and the polymer fluorescence unit through hydrogen bonding, which effectively improve the luminescence efficiency.

Key words: Chirality, Polymers of intrinsic microporosity, Chiral recognition, Fluorescence recognition, Phenylalanine