Synthesis and characterization of new poly(aryl ether ketone)s bearing (4-phenoxyphenyl)triphenylmethane moieties

1,1-Bis(4-hydroxyphenyl)-1-(4-phenoxyphenyl)-1-phenylmethane (BHPPPPM), a new bisphenol monomer, was synthesized with 65% yield from 4-benzoyl diphenyl ether in a one-pot, two-step synthetic procedure. Four new poly(aryl ether ketone)s (PAEKs) bearing (4-phenoxyphenyl)triphenylmethane moieties were prepared from BHPPPPM with four difluorinated aromatic ketones via a nucleophilic substitution reaction. The polycondensation proceeded in tetramethylene sulfone in the presence of anhydrous potassium carbonate and afforded the new PAEKs in nearly quantitative yields with inherent viscosities of 0.60-0.78 dL g(-1). The resulting PAEKs having number-average molecular weights in the range of 29,500-34,200 g mol(-1) with the polydispersity index ranged from 1.94 to 2.01 are all amorphous and show high glass transition temperatures ranging from 174 degrees C to 196 degrees C, excellent thermal stability, and the temperatures at the 5% weight loss are over 500 degrees C with char yields above 60% at 700 degrees C under nitrogen atmosphere. These new PAEKs are all soluble in polar aprotic solvents such as N-methyl-2-pyrrolidone and N,N-dimethylacetamide and could also be dissolved in chloroform and tetrahydrofuran. All the polymers formed transparent, strong, and flexible films with tensile strengths of 78-85 MPa, tensile moduli of 1.9-2.4 GPa, and elongations at break of 7-10%.