Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation

• Published in: Amino acids 2009-03, Vol.36 (3), p.511-518
• Main Authors: Hajipour, Abdol R, Zahmatkesh, Saeed, Roosta, Parniyan, Ruoho, Arnold E
• Format: Article
• Language: English
• Subjects: Acetic acid; Amino acids; Amino Acids - chemical synthesis; Amino Acids - chemistry; Analytical Chemistry; Azo Compounds - chemical synthesis; Azo Compounds - chemistry; Biochemical Engineering; Biochemistry; Biomedical and Life Sciences; biphenyl; condensation reactions; Dianhydrides; diazo compounds; Diphenols; diphenyl ethers; Ethers; Imides - chemical synthesis; Imides - chemistry; Joining; Life Sciences; methane; methylene chloride; Neurobiology; Optical activity; Original Article; phenol; Polymers - chemical synthesis; Polymers - chemistry; Proteomics; pyridines; Refluxing; sodium nitrite; temperature
• ISSN: 0939-4451; 1438-2199
• DOI: 10.1007/s00726-008-0113-y

N,N'-Pyromelliticdiimido-di-l-amino acids (1a-1d) were prepared from the reaction of pyromellitic dianhydride with the corresponding l-amino acids in a solution of glacial acetic acid/pyridine (3:2) at refluxing temperature. 4,4'-sulfonyl bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol, 4,4'-oxy bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol and 4,4'-methylene bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol, were prepared from 4,4'-diamino diphenyl sulfone, 4,4'-diamino diphenyl ether, 4,4'-diamino diphenyl methane, sodium nitrite and phenol following the general procedure of diazo coupling. Interfacial polycondensation method was used to prepare the corresponding poly(azo-ester-imid)s (PAEI ₁₋₁₂ ) in biphasic solution of water/dichloromethane. The resulting polymers (PAEIs) have been obtained in high yields having good inherent viscosities (0.32-0.57 dl g⁻¹), optical activities and thermal stabilities.