Step‐growth polymerization of 5‐[(9,10‐dihydro‐9,10‐ethanoanthracene‐11,12‐dicarboximido)‐3‐methylbutanoyl‐amino]isophthalic acid with aromatic diols

Abstract

cis-9,10-dihydro-9,10-ethanoanthracene-11,12dicarboxylic acid anhydride (1) was converted to imide acid (2) by reaction with S-valine. Compound 2 was converted to the acid chloride (3) by reaction with thionyl chloride and then treated with 5-aminoisophthalic acid in dry N,N-dimethylacetamide to obtain 5-[(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)-3-methylbutanoylamino]isophthalic acid (4). Direct step-growth polymerization of this novel chiral diacid monomer 4 with a series of different diols in a system of tosyl chloride, pyridine, and N,Ndimethylformamide was carried out. The optically active polyesters (PEs) were obtained with good yield and moderate inherent viscosity ranging from 0.23 to 0.48 dL/g. The resulting polymers were characterized with FTIR, 1 H-NMR, and elemental analysis techniques. The prepared PEs showed good thermal stability up to 320 C as measured by thermogravimetric analysis. Specific rotation experiments demonstrated the induction of optical activity due to successful insertion of S-valine in the structure of pendant groups.

Bionanocomposites Preparation and Characterization: Dispersion of Surface-Modified ZnO Nanoparticles in Optically Active Poly(Amide-Imide) Derived from 3,5-Diamino-N-(4-Hydroxyphenyl)Benzamide and Amino Acid

“…Mallakpour et al [19][20][21][22] prepared amino-acid-containing monomers that containing the chiral units in the main as well as in the side-chains. They proposed that N ,N -(pyromellitoyl)-bis-L-phenylalanine diacid chloride (1) has great advantages due to the presence of imide linkage and benzene rings for thermal stability and increasing the flexibility of the diacid chloride structure.…”

“…Among the different kind of functional polymers PAIs have great interest, due to the favorable balance between processability and performance that being a promising matrix candidate for hybrid materials. Also commence chiral units in PAIs structures caused to bearing additional advantage and application fields such as biodegradability, catalytic and separation chemistry for these kinds of polymers [19][20][21][22][23][24].…”