Synthesis of high performance polyamides utilizing copper-catalyzed amidation of a dibromoarene with different diamides

Abstract

A series of diphenylquinoxaline-containing polyamides were prepared from the condensation polymerization of 2,3-bis (4-bromophenyl) quinoxaline (DBQ) with various primary and secondary diamides via copper-catalyzed amidation reaction. The polyamides were characterized with FTIR, NMR, GPC, differential scanning calorimeter, and thermo gravimetric analysis, and their solubility and viscosity were measured. The polyamides synthesized here are amorphous and showed relatively good solubility in polar aprotic solvents and demonstrate the ability to form brownish hard films by solvent casting; their inherent viscosities ranged from 49 to 55 mL/g. The average molecular weights of polyamides were in the range of Mw = 11,950–5592 g/mol (MWD = 1.21–1.87). These polyamides had relatively high thermal stability with Tg values up to 276°C, 10% weight loss temperatures (T10%) in the range of 364–476°C, and char yields at 600°C in N2 up to 72%. They also exhibit emission in the solid state and in dilute (0.2 g/dL) DMAc solution at 425–484 nm with photoluminescence quantum (ϕf) yields in the range of 14–23%. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012