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    朱睿琪, 孙军, 周艳丽, 周正金, 邱原, 刘旭东, 张春红. 以L-丙氨酸衍生物为侧链的螺旋聚苯乙炔的合成及其阴离子识别性能[J]. 功能高分子学报, 2019, 32(6): 741-746. doi: 10.14133/j.cnki.1008-9357.20190607001
    引用本文: 朱睿琪, 孙军, 周艳丽, 周正金, 邱原, 刘旭东, 张春红. 以L-丙氨酸衍生物为侧链的螺旋聚苯乙炔的合成及其阴离子识别性能[J]. 功能高分子学报, 2019, 32(6): 741-746. doi: 10.14133/j.cnki.1008-9357.20190607001
    ZHU Ruiqi, SUN Jun, ZHOU Yanli, ZHOU Zhengjin, QIU Yuan, LIU Xudong, ZHANG Chunhong. Synthesis and Anion Recognition Ability of Helical Poly(phenylacetylene) Bearing L-Alanine Derivative Pendants[J]. Journal of Functional Polymers, 2019, 32(6): 741-746. doi: 10.14133/j.cnki.1008-9357.20190607001
    Citation: ZHU Ruiqi, SUN Jun, ZHOU Yanli, ZHOU Zhengjin, QIU Yuan, LIU Xudong, ZHANG Chunhong. Synthesis and Anion Recognition Ability of Helical Poly(phenylacetylene) Bearing L-Alanine Derivative Pendants[J]. Journal of Functional Polymers, 2019, 32(6): 741-746. doi: 10.14133/j.cnki.1008-9357.20190607001

    L-丙氨酸衍生物为侧链的螺旋聚苯乙炔的合成及其阴离子识别性能

    Synthesis and Anion Recognition Ability of Helical Poly(phenylacetylene) Bearing L-Alanine Derivative Pendants

    • 摘要:L-丙氨酸以及具有阴离子识别功能的酰胺基引入到苯乙炔单体中,合成光学活性苯乙炔单体PAA-L-Ala。在铑系催化剂的作用下,实现PAA-L-Ala的聚合,合成光学活性聚苯乙炔衍生物PPAA-L-Ala。通过圆二色光谱、荧光光谱、紫外-可见吸收光谱及裸眼检测等手段,考察了PPAA-L-Ala对阴离子的识别性能。结果表明:聚合物主链具有动态螺旋构象。PPAA-L-Ala具有阴离子识别能力,分别通过圆二色光谱、荧光光谱实现了对AcO\rmH_2PO_4^-、OH和F等离子的识别;通过紫外-可见吸收光谱及裸眼检测,实现了对F及OH的有效识别。

       

      Abstract: 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, \rm H_2PO_4^-, 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.

       

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