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Preparation of thermally stable and optically active organosoluble aromatic polyamides containing L-leucine amino acid under green conditions

机译:在绿色条件下制备含L-亮氨酸氨基酸的热稳定且光学活性的有机可溶性芳族聚酰胺

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摘要

An optically active bulky dicarboxylic acid (2S)-4-[(4-methyl-2-phthalimidylpentanoylarnino)benzoylamino]isophthalic acid (1), was synthesized in five step starting from L-leucine and phthalic anhydride. A set of new aromatic polyamides containing (N-phthaloyl-L-leucine) units was synthesized by the direct one-pot phosphorylation polycondensation of diacid 1 with various aromatic diamines in the presence of different imidazolium salts and triphenyl phosphite (TPP) without adding extra compounds (Method I). This method was compared with a classical method in a medium consisting of TPP, N-methyl-2-pyrrolidinone, pyridine, and calcium chloride (Method II) and the results are comparable. The polymers were produced with high yields and from moderate to high inherent viscosities (0.43-0.81 dL g~(-1)). Amino acid existence in this backbone results in optically active polymers. The chemical structures of some of these polymers were characterized by ~1H-NMR and elemental analysis, and all of them with FT-IR and specific rotation tools. By introduction of bulky and flexible clusters in these new polyamides pendent group; make them soluble in most polar aprotic solvents.
机译:从L-亮氨酸和邻苯二甲酸酐开始,以五个步骤合成了光学活性的大块二羧酸(2S)-4-[(4-甲基-2-邻苯二甲酰亚胺基戊酰基亚氨基)苯甲酰基氨基]间苯二甲酸(1)。在不同咪唑鎓盐和亚磷酸三苯酯(TPP)存在下,通过将二酸1与各种芳族二胺直接一锅磷酸化缩聚反应,合成了一组包含(N-邻苯二甲酰基-L-亮氨酸)单元的新型芳族聚酰胺。化合物(方法I)。将该方法与传统方法在由TPP,N-甲基-2-吡咯烷酮,吡啶和氯化钙组成的介质中进行了比较(方法II),结果可比。该聚合物以高收率和中等至高的比浓对数粘度(0.43-0.81 dL g〜(-1))生产。在该主链中存在氨基酸产生光学活性聚合物。其中一些聚合物的化学结构通过〜1H-NMR和元素分析进行​​了表征,并且所有这些均通过FT-IR和特定的旋转工具进行了表征。通过在这些新的聚酰胺悬垂组中引入笨重而灵活的簇;使它们可溶于大多数极性非质子溶剂。

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