Synthesis and characterization of novel aromatic polyamides containing 3-trifluoromethyl-substituted triphenylamine

A new 3-trifluoromethyl-substituted triphenylamine-containing aromatic diacid monomer, N,N-bis(4-carboxyphenyl)-3-trifluoromethylaniline, was prepared by the substitution reaction of 3-trifluoromethylaniline with 4-fluorobenzonitrile, followed by alkaline hydrolysis of the dinitrile intermediate. Novel aromatic polyamides with 3-trifluoromethyl-substituted triphenylamine moieties were prepared from the diacid and various aromatic diamines via the direct phosphorylation polycondensation. All the polyamides were amorphous and readily soluble in many polar organic solvents such as N,N-dimethylacetamide and N-methyl-2-pyrrolidone, and could be solution-cast into transparent, tough, and flexible films with good mechanical properties. They exhibited good thermal stability with relatively high glass-transition temperatures (258-327 degrees C), 10% weight-loss temperatures above 500 degrees C, and char yields higher than 60% at 800 degrees C in nitrogen. These polymers had low dielectric constants of 3.22-3.70 (100 Hz), low moisture absorption in the range of 1.75-2.58%, and high transparency with an ultraviolet-visible absorption cut-off wavelength in the 375-395nm range. Cyclic voltammograms of the polyamide films cast onto an indium tin oxide coated glass substrate exhibited a reversible oxidation redox couple with oxidation half-wave potentials (E-1/2) of 0.95-1.00V vs. Ag/AgCl in an acetonitrile solution.