A series of Diels–Alder polyarylene polymers were synthesized via traditional oil bath and microwave-assisted step-growth polymerization. Optimization of the reaction of bistetracyclone with 1,4-diethynylbenzene using a variety of solvents, concentration, and time was achieved. The polyarylene polymers were characterized by 1H, 13C, and 19F NMR spectroscopy, ATR-FTIR spectroscopy, TGA, DSC, DMA, and GPC. Diphenyl ether (Ph2O) worked well for oil bath synthesis whereas polar solvents (e.g., tetrahydrofuran and nitrobenzene) worked well for microwave-assisted polymerization. Thermal analysis showed little change in the series of polymers for onset of decomposition (Td = 550 °C). Molecular weights were monitored over time affording well over 100 kg/mol and dispersities more difficult to control in the range 2.0 to 20.1. Applications will be discussed including proton exchange membrane fuel cells, gas separation membranes, coatings, semi-fluorinated optics, and polyimide resins.

Polyarylene synthesis, characterization, and optimization for high performance applications

256th National Meeting (2018)

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