Microwave-assisted synthesis and characterization of optically active poly (ester-imide)s incorporating l-alanine

• Published in: Amino acids 2010-04, Vol.38 (4), p.1253-1260
• Main Authors: Zahmatkesh, Saeed, Hajipour, Abdol R.
• Format: Article
• Language: English
• Subjects: Alanine - analogs & derivatives; Alanine - chemistry; Amino acids; Analytical Chemistry; Benzoates - chemistry; Benzophenones - chemistry; Biochemical Engineering; Biochemistry; Biomedical and Life Sciences; Chlorides; Cobalt; Diols; Hot Temperature - adverse effects; Hydrocarbons, Aromatic - chemistry; Hydrocarbons, Aromatic - radiation effects; Imides - chemical synthesis; Imides - chemistry; Life Sciences; Magnetic Resonance Spectroscopy; Microwaves; Molecular Structure; Neurobiology; Optical activity; Original Article; Ovens; Photochemical Processes; Piperazines - chemistry; Piperazines - radiation effects; Polyesters - chemical synthesis; Polyesters - chemistry; Polyetherimides; Polyethylene Glycols - chemistry; Polyethylene Glycols - radiation effects; Polymers; Proteomics; Solubility; Solvents; Spectrophotometry, Infrared; Stereoisomerism; Time Factors; Viscosity
• ISSN: 0939-4451; 1438-2199
• DOI: 10.1007/s00726-009-0336-6

Pyromellitic dianhydride (1) was reacted with L-alanine (2) to result [ N,N′ -(pyromellitoyl)-bis- l -alanine diacid] (3). This compound (3) was converted to N,N′ -(pyromellitoyl)-bis- l -alanine diacyl chloride (4) by reaction with thionyl chloride. The microwave-assisted polycondensation of this diacyl chloride (4) with polyethyleneglycol-diol ( PEG-200 ) and/or three synthetic aromatic diols furnish a series of new PEI s and Co-PEI s in a laboratory microwave oven (Milestone). The resulting polymers and copolymers have inherent viscosities in the range of 0.31–0.53 dl g −1 . These polymers are optically active, thermally stable and soluble in polar aprotic solvents such as DMF, DMSO, NMP, DMAc, and sulfuric acid. All of the above polymers were fully characterized by IR spectroscopy, 1 H NMR spectroscopy, elemental analyses, specific rotation and thermal analyses. Some structural characterizations and physical properties of these optically active PEI s and Co-PEI s have been reported.