Microwave irradiation as a versatile tool for increasing reaction rates and yields in synthesis of optically active polyamides containing flexible l-leucine amino acid

Abstract

In this investigation, a series of thermally stable and optically active polyamides (PA)s containing bulky pendant chiral functionality from polymerization of a diacid monomer containing rigid phthalimide and flexible L-leucine groups, (2S)-5-[4-(4-methyl-2-phthalimidylpentanoylamino)benzoylamino]isophthalic acid with several aromatic and aliphatic diisocyanates such as 4,4'-methylenebis(phenyl isocyanate), toluylene-2,4-diisocyanate, isophorone diisocyanate, and hexamethylene diisocyanate under gradual heating method were prepared and compared with microwave-assisted polycondensation method. The polymerization reactions occurred rapidly under microwave irradiation and produced a series of PAs with good yields and moderate inherent viscosities of 0.26-0.68 dL/g. All of the new PAs showed good solubility and were readily dissolved in aprotic organic solvents. The resulting polymers were characterized by FT-IR, (1)H NMR spectroscopy, and elemental analysis technique. Thermal stability and thermal properties of PAs were evaluated by thermogravimetric analysis and differential scanning calorimetry. The interpretation of kinetic parameters (E, Delta H, Delta S, and Delta G) of thermal decomposition stages have been evaluated using Coats-Redfern equations.