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首页> 外文期刊>Macromolecules >Helicity Induction on Poly(phenylacetylene)s Bearing Phosphonic Acid Pendants with Chiral Amines and Memory of the Macromolecular Helicity Assisted by Interaction with Achiral Amines in Dimethyl Sulfoxide
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Helicity Induction on Poly(phenylacetylene)s Bearing Phosphonic Acid Pendants with Chiral Amines and Memory of the Macromolecular Helicity Assisted by Interaction with Achiral Amines in Dimethyl Sulfoxide

机译：带有手性胺的磷酸侧链的聚苯乙炔的螺旋诱导和在二甲基亚砜中与非手性胺相互作用辅助的大分子螺旋的记忆

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摘要

Two novel stereoregular poly(phenylacetylene)s bearing a phosphonic acid residue (poly-1) and its monoethyl ester (poly-2) as pendants were prepared by the polymerization of diethyl (4-ethynylphenyDphosphonate followed by hydrolysis of the diethyl ester groups and polymerization of ethyl (4-ethynylphenyl)phosphonate,respectively.The polymers were found to form a predominantly one-handed helical conformation upon complexation with various chiral amines through noncovalent acid-base interactions in dimethyl sulfoxide (DMSO).The complexes exhibited an induced circular dichroism (ICD) in the UV-visible region of the polymer backbones.In particular,poly-2 is an induced helical polymer more sensitive to the chirality of amines than poly-1 and poly((4-carboxyphenyl)acetylene) and yields the same Cotton effect sign when complexed with chiral amines of the same absolute configuration.Moreover,the macromolecular helicity of poly-1 and poly-2 induced by chiral amines was "memorized" after the chiral amines were completely removed and replaced with various achiral diamines and oligoamines in DMSO.In sharp contrast to the same memory effect on the induced helical poly((4-carboxyphenyl)acetylene),the helical structures of poly-1 and poly-2 could not be efficiently maintained by achiral monoamines.The effect of the structure of the achiral diamines and oligoamines on the efficiency of the helicity retention and the stability of the memorized polymers were also investigated.
机译：通过将二乙基（4-乙炔基苯基膦酸酯）聚合，然后水解二乙基酯基团并进行聚合反应，制备了两个带有膦酸残基（poly-1）及其单乙基酯（poly-2）的立体规整型聚苯乙炔。通过在二甲基亚砜（DMSO）中通过非共价酸-碱相互作用，与各种手性胺络合后，发现该聚合物主要形成单手螺旋构象。 （ICD）在聚合物主链的UV可见区域中。尤其是，poly-2是一种诱导的螺旋聚合物，比poly-1和poly（（4-羧苯基）乙炔）对胺的手性更敏感，并且产生相同的与相同绝对构型的手性胺络合时，具有棉花效应迹象。此外，在手性后，“记忆”了由手性胺诱导的poly-1和poly-2的大分子螺旋。在DMSO中完全清除了所有的芳族胺，并用各种非手性二胺和低聚胺替代。与相同的对诱导的螺旋聚（4-羧基苯基）乙炔的记忆效应形成鲜明对比的是，poly-1和poly-2的螺旋结构可以还研究了非手性二胺和低聚胺的结构对保持螺旋性的效率和记忆聚合物的稳定性的影响。

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