Synthesis and characterization of new optically active and organosoluble poly(ester-imide)s based on bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic diimide by direct polycondensation  

作　　者：FAGHIHI Khalil SHABANIAN Meisam HAJIBEYGI Mohsen 

机构地区：[1]Organic Polymer Chemistry Research Laboratory,Department of Chemistry,Faculty of Science,Arak University

出　　处：《Science China Chemistry》2010年第4期898-904,共7页中国科学（化学英文版）

摘　　要：New optically active poly(ester-imide)s PEIs were prepared from newly synthesized N,N′-(bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic)-bis-L-isoleucine diacid 4 via direct polycondensation with various aromatic diols in a system of tosyl chloride (TsCl), pyridine (Py), and N,N-dimethylformamide (DMF). The reactions with bicyclo TsCl were significantly promoted by controlling alcoholysis with diols, in the presence of catalytic amounts of DMF, to give a series of optically active PEIs, with good yield and moderate inherent viscosity ranging from 0.44 to 0.66 dL/g. The diacid 4 was synthesized by the condensation reaction of [2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride 1 with L-isoleucine 2 in acetic acid. All of these polymers were highly organosoluble in solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), and N-methyl-2-pyrrolidone (NMP) at room temperature. They were fully characterized by means of NMR spectroscopy, FTIR spectroscopy, gel permeation chromatography (GPC), elemental analyses, inherent viscosity, solubility test, and specific rotation, and thermal properties of the poly(ester-imide)s were investigated using TGA/DTG.New optically active poly(ester-imide)s PEIs were prepared from newly synthesized N,N′-(bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic)-bis-L-isoleucine diacid 4 via direct polycondensation with various aromatic diols in a system of tosyl chloride (TsCl), pyridine (Py), and N,N-dimethylformamide (DMF). The reactions with bicyclo TsCl were significantly promoted by controlling alcoholysis with diols, in the presence of catalytic amounts of DMF, to give a series of optically active PEIs, with good yield and moderate inherent viscosity ranging from 0.44 to 0.66 dL/g. The diacid 4 was synthesized by the condensation reaction of [2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride 1 with L-isoleucine 2 in acetic acid. All of these polymers were highly organosoluble in solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), and N-methyl-2-pyrrolidone (NMP) at room temperature. They were fully characterized by means of NMR spectroscopy, FTIR spectroscopy, gel permeation chromatography (GPC), elemental analyses, inherent viscosity, solubility test, and specific rotation, and thermal properties of the poly(ester-imide)s were investigated using TGA/DTG.

关 键 词：poly(ester-imide)s direct POLYCONDENSATION optically active polymers L-ISOLEUCINE 

分 类 号：O633.22[理学—高分子化学]