来自 N,N'-(bicyclo[2,2,2]oct-7-ene-2,3,5,6-四羧酸)双-l-苯基丙氨酸和芳族二胺的新型光学活性聚（酰胺-酰亚胺） : 合成和表征,Polymer Bulletin

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来自 N,N'-(bicyclo[2,2,2]oct-7-ene-2,3,5,6-四羧酸)双-l-苯基丙氨酸和芳族二胺的新型光学活性聚（酰胺-酰亚胺） : 合成和表征
Polymer Bulletin ( IF 3.1 ) Pub Date : 2009-10-22 , DOI: 10.1007/s00289-009-0162-8
Hossein Nasr Isfahani , Khalil Faghihi , Mohsen Hajibeygi , Mehdi Bokaei

在这项工作中，通过 N 的反应制备了具有双环 [2,2,2]oct-7-ene-2,3,5,6-四羧酸二酰亚胺基团的新型光学活性聚（酰胺-酰亚胺）（PAI） ,N'-(bicyclo[2,2,2]oct-7-ene-2,3,5,6-四羧酸)双-1-苯基丙氨酸 (4) 作为二酸单体与各种容易获得的芳族二胺。在氯化钙 (CaCl2) 和 N-甲基-2-吡咯烷酮 (NMP) 存在下，亚磷酸三苯酯 (TPP)/吡啶 (Py) 已成功应用于直接缩聚。二酸 (4) 通过双环 [2,2,2]oct-7-ene-2,3,5,6-四羧酸二酐 (1) 与 l-苯丙氨酸 (2) 在乙酸中的缩合反应合成解决方案。得到的新聚合物收率良好，特性粘度范围在 0.29 和 0.48 dLg-1 之间，并通过元素分析、FT-IR、1H-NMR 光谱进行表征，比旋光度和热重分析（TGA、DTG）技术。热重分析表明聚合物在 600 °C 下的残余重量百分比在 53.80 和 56.21% 之间，这表明这些聚合物具有中等的热稳定性。此外，由于这些聚合物的手性中心和旋光性的存在，它们有可能用作色谱技术中分离外消旋混合物的手性固定相。

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New optically active poly(amide-imide)s from N,N′-(bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic)bis-l-phenyl alanine and aromatic diamines: synthesis and characterization

In this work, new optically active poly(amide-imide)s (PAIs) having bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic diimide groups were prepared by the reaction of N,N′-(bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic)bis-l-phenyl alanine (4) as a diacid monomer with various readily available aromatic diamines. Triphenyl phosphite (TPP)/pyridine (Py) in the presence of calcium chloride (CaCl2) and N-methyl-2-pyrrolidone (NMP) were successfully applied for direct polycondensation. The diacid (4) was synthesized by the condensation reaction of bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (1) with l-phenyl alanine (2) in acetic acid solution. The resulting new polymers were obtained in good yields, inherent viscosities ranging between 0.29 and 0.48 dLg−1 and were characterized with elemental analysis, FT-IR, 1H-NMR spectroscopy, specific rotation, and thermal gravimetric analysis (TGA, DTG) techniques. Thermogravimetric analysis indicated that the residual weight percent of polymers at 600 °C was between 53.80 and 56.21%, which show these are moderately thermally stable. In addition because of existence of chiral center and optical activity of these polymers, they have potential to be used as chiral stationary phase in chromatography technique for the separation of racemic mixtures.

更新日期：2009-10-22

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