Synthesis and characterization of organo-soluble polyamides containing triaryl imidazole pendant and ether linkage moieties: Thermal, photophysical, and chemiluminescent properties

Abstract

A new symmetrical diamine monomer containing a triaryl imidazole pendant group was successfully synthesized by the nucleophilic substitution of hydroquinone with the synthesized 2-(2-chloro-5-nitrophenyl)-4, 5-diphenyl-1H-imidazole (I). A series of novel polyamides were prepared from the diamine monomer and various aliphatic and aromatic dicarboxylic acids via phosphorylation polyamidation. These polyamides are readily soluble in many organic solvents; their inherent viscosities ranged from 0.68 to 0.89dl/g and gave tough and flexible films by solution-casting. They had useful levels of thermal stability associated with relatively high Tgs (186-278°C), 10% weight loss temperatures in the range of 355-482°C, and char yields at 600°C in air up to 67%. All the polyamides have fluorescence emission in dilute (0.2g/dl) DMAc solution with maxima at 425-495nm and with the quantum yields in the range 14-28%. The chemiluminescence activity of polyamides was also studied in the presence of peroxyoxalate. © 2010 John Wiley & Sons, Ltd.