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Anion recognition is closely related to human life activities and of great significance to human life and its social progress. Therefore, the recognition of anions in high-performance has been the focus of research in recently years. Poly(phenylacetylene) derivatives possessing helical conformation in main chains have good optical activity and unique properties, and have potential applications in anion recognition and luminescence materials. In this work, a novel substituted poly(phenylacetylene) derivative containing amino acid and group with the function of anion recognition was synthesized, and optical activities and anion recognition abilities of the polymer were also investigated. L-alanine residue and amide group having anion recognition ability were introduced to phenylacetylene monomer, and phenylacetylene monomer (PAA-L-Ala) with optical activity was successfully synthesized via amidation reaction, deprotection of Boc group and amidation reaction. The phenylacetylene monomer was successfully polymerized in DMF (N,N-dimethylformamide) using a rhodium catalyst to yield a optically active poly(phenylacetylene) derivative (PPAA-L-Ala). The optical activities of polymer and monomer were investigated by the specific rotation and circular dichroism. The results show that the back bone of the polymer possesses a dynamic helical conformation induced by the asymmetric chiral residue. The anion recognition ability of the novel poly(phenylacetylene) derivative was evaluated using a series of tetra-n-butylammonium salts in DMF. The results indicate that PPAA-L-Ala has anion recognition ability, which can be used as a probe for selective recognition of AcO-H2PO4-OH- and F- based on circular dichroism or fluorescence spectrometer, and a probe for selective recognition of OH-and F- based on naked eyes and UV-Vis. [ABSTRACT FROM AUTHOR]