Direct polycondensation of N‐trimellitylimido‐L‐isoleucine with aromatic diamines

Abstract

N-Trimellitylimido-l-isoleucine (3) was prepared from the reaction of trimellitic anhydride with lisoleucine [l-2-amino-3-methylvalerianic acid or (2S,3S)-2-amino-3-methyl-n-valerinic acid] in an N,N-dimethylformamide solution at the refluxing temperature. The direct polycondensation reaction of the monomer imide diacid (3) with 1,4-phenylenediamine, 4,4Ј-diaminodiphenylmethane, 4,4Ј-diaminodiphenylsulfone, diaminodiphenylether, 1,5-naphthalendiamine, 2,4-diaminotoluene, and 1,3-phenylenediamine was performed in a medium consisting of triphenyl phosphite, N-methyl-2-pyrolidone (NMP), pyridine, and calcium chloride. The polycondensation was performed under two different conditions: in one method, the reaction mixture was heated in an NMP solution at 60, 90, and then 130°C for different periods of time, and in the other method, the reaction mixture was refluxed only for 1 min in the same solvent. The resulting poly(amide imide)s (PAIs), with inherent viscosities of 0.21-0.37 dL/g, were obtained in high yields. All of these compounds were fully characterized by IR spectra, elemental analyses, and specific rotation measurements. Some structural characterizations and physical properties of these new optically active PAIs were examined.

Nanostructure Formation in Chiral Poly(amide-Imide)s Based on Dopamine Moiety and N-Trimellitylimido-L-Amino Acids in the Main Chain

“…Optically active diacid monomers (7a-7d) such as: N-trimellitylimido-L-leucine [36], N-trimellitylimido-L-isoleucine [37], N-trimellitylimido-Svaline [38], and N-trimellitylimido-L-alanine [39] were prepared according to previous works (Scheme 2).…”

“…Diacid monomers were synthesized by the condensation reaction of an equimolar amount of trimellitic anhydride (5) and different amino acids [L-leucine, L-isoleucine, S-valine, and L-alanine (6a-6d)] in reflux acetic acid solution, as shown in Scheme 2 [36][37][38][39].…”

Advances in synthetic optically active condensation polymers - A review

“…Synthesis and characterization of a number of optically active poly(amide-imide)s (PAI)s were investigated by Mallakpour's group [151][152][153][154]. The polymerization reactions were carried out via polycondensation reaction of N-trimellitylimidoleucine, N-trimellitylimidoisoleucine, N-trimellitylimidophenylalanine and N-trimellitylimido-DL and Lalanine with several diamines in the presence of TPP, NMP, Py, and CaCl 2 under various conditions for different periods of time, and in another method ( Figure 13).…”

“…These PEIs showed optical rotation and were readily soluble in various organic solvents and had moderate thermal stability. The same researchers also used L-isoleucine amino acid as a biocompatible material as well as optically active pure and chemical functional group in the polymer backbone for the formation of a series of new PEIs by direct polyesterification from aromatic diols and imide dicarboxylic acid which was prepared from trimellitic anhydride and L-isoleucine amino acid in a system of TsCl/Py/DMF [219] (Figure 21). Mallakpour's group also reported on [220] …”

Synthesis and Characterization of Novel Organosoluble, Thermal Stable and Optically Active Polyesters Derived from 5-(2-Phthalimidiylpropanoylamino)isophthalic Acid

“…Recently, we have synthesized a variety of OAPs by different methods, such as modification of polybutadiene with an optically active substituted urazole group, Diels-Alder-Ene reactions, and the reaction of an optically active monomer with a number of diamines via solution polymerization. [21][22][23] In the last case, we use amino acids as a chiral agent in the backbone of the macromolecules. Because the amino acids are naturally occurring compounds, synthetic polymers based on amino acids are anticipated to be nontoxic, biocompatible, and biodegradable.…”