Polycarbazole Copolymers from 3-(4-Fluorobenzoyl)carbazole and 4,4′-Biphenol via Combined C-N and C-O Coupling Reactions with Activated Difluorides

2010 
3-(4-Fluorobenzoyl)carbazole was synthesized by a Friedel-Crafts reaction of carbazole with 4-fluorobenzoylchloride. 1H-NMR and MALDI-TOF MS confirmed the structure and the purity. Copolymers of these NH/OH-containing monomers were prepared with 4, 4′-biphenol and bis(4-fluorophenyl)sulfone as comonomers by combined C-O and C-N coupling reactions with activated difluorides. These copolymers were soluble in N-methylpyrrolidinone (NMP), dimethylsulfoxide (DMSO), N,N-dimethylacetamide (DMAc) and dimethylformamide (DMF). The inherent viscosities of the copolymers in NMP solutions at 30°C were all around 0.8 dL/g. They could be easily cast into tough films from NMP solutions. The copolymers exhibited Tgs ranging from 238°C to 282°C. Thermal stabilities by TGA showed no weight loss below 400°C and the temperatures of 5% weight loss ranged from 535°C to 558°C. The homopolymer of 3-(4-fluorobenzoyl)carbazole was insoluble in common solvents and had a Tg of 332°C, and temperature of 5% weight loss of 560°C. UV-VIS...
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