Synthesis and characterization of novel organosoluble and optically active aromatic polyesters containing l-methionine and phthalimide pendent groups

Abstract

5-(4-Methylthio-2-phthalimidylbutanoylamino)isophthalic acid (5) as a novel diacid monomer containing phthalimide and flexible chiral groups was prepared by dehydration of L: -methionine and phthalic anhydride followed by reacting with thionyl chloride and then treating with 5-aminoisophthalic acid (5AIPA) in dry N,N-dimethylacetamide (DMAc). A series of novel polyesters (PEs) containing phthalimide group was prepared by the reaction of diacid monomer 5 with several aromatic diols via direct polyesterification with tosyl chloride/pyridine/dimethylformamide (DMF) system as condensing agent. The resulting new polymers were obtained in good yields and inherent viscosities ranging between 0.21 and 0.51 dLg(-1) were characterized with FT-IR, 1H NMR, elemental and thermogravimetric analysis techniques. These polymers are readily soluble in polar organic solvents such as DMAc, DMF, dimethyl sulfoxide and protic solvents such as sulfuric acid. Specific rotation experiments demonstrate the optical activity induction due to successful insertion of L-methionine in the structure of pendent groups. Thermogravimetric analysis showed that the 10% weight loss temperature in a nitrogen atmosphere were more than 315 degrees C, which indicates that the resulting PEs have good thermal stability.

Advances in synthetic optically active condensation polymers - A review

“…Recently, Mallakpour and coworkers [127][128][129][130][131] synthesized optically active thermally stable aromatic polyesters (PE)s containing phthalimide group from the reaction of two different diacid monomer with several aromatic diols via direct polyesterification with tosyl chloride (TsCl)/Py/ Figure 10. Synthesis of optically active coPIs derived from DAn [119][120][121][122][123] DMF system as condensing agent.…”

Ionic Liquid as a Green Media for Rapid Synthesis of Optically Active Organosoluble Polyamides

“…5-(4-Methylthio-2-phthalimidybutanoylamino)isophthalic acid (1) as an optically active diacid monomer was prepared according to our previous work in successful synthesis of new organosoluble optically active aromatic polyesters [50].…”

Synthesis, characterization, and soil biodegradation study of polyamides derived from the novel bioactive diacid monomer 5‐(2‐phthalimidoethanesulfonamido) isophthalic acid

“…Thus, thermally stable PAs with pendent aromatic or heteroaromatic rings have been reported 6. The introduction of pendent imide rings with their high thermoresistance will also improve both the solubility and thermal stability 7, 8…”