Novel perfluorocyclohexenyl aryl ether homo- and copolymers were obtained by step-growth condensation polymerization at 80 °C in dimethyl formamide of bisphenols containing aromatic cores with decafluorocyclohexene under basic conditions. Bisphenols with polycyclic aromatic hydrocarbon (PAH) cores were synthesized by reacting acenapthenequinone (or phenanthrenequinone) with excess phenol under acidic conditions to afford three monomers: M1, M2, and M3 (Scheme 1). The chemical structures of the as-synthesized bisphenols were validated by Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (NMR), and single-crystal X-ray diffraction analyses. The physico-chemical and thermal properties of the as-synthesized PFCH polymers were evaluated by FTIR, NMR, gel permeation chromatography (GPC), and differential scanning calorimetry (DSC) and thermogravimetric analyses (TGA), respectively. DSC analyses of PFCH polymers showed significant variations in the glass transition temperatures (Tg) ranging from 170 – 240 °C, which were dependent on the PAH type and the type of substitution on the PAHs. However, no variations in the thermal stabilities were observed. The onset of decomposition onset (Td 5%) was observed at 340-350 and 350-360°C in air and nitrogen atmospheres, respectively. By this work, we highlight development of PFCH polymers containing enchained PFCH olefin and PAH moieties for application in optics and opto-electronics, where high thermal stabilities and high Tgs are desired.

Synthesis and characterization of Perfluorocyclohexenyl Aryl Ether (PFCH) polymers with divergent glass transition temperatures

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.