Abstract:
Triphenylene-containing trifluorovinyl ether monomers prepared from 2,3-disubstituted-bis-1,4-(p-bromophenyl)triphenylene core building blocks undergo thermal step-growth polymerization (Ph2O, 180 °C), affording perfluorocyclobutyl polymers with unprecedented glass-transition temperatures (up to 295 °C), excellent high thermal-oxidative stabilities, and solution processability. The modular synthetic route provides access to a series of triphenylene monomers from a common cyclopentadienone derivative and variably substituted alkynes, which polymerize thermally to solution-processable, tough, transparent films with bright blue solid-state photoluminescence (λem = ∼400–470 nm). Conversion was monitored by 19F NMR end-group analysis and gel permeation chromatography to reasonably high molecular weights (Mn = 45–93 kDa). Remarkably, photoemission persists at 250 °C in air for 24 h with negligible changes in absorbance and emission wavelengths after cooling to room temperature.
Farajidizaji, B., Borrego, E.I., Athukorale, S., Jazi, M., Donnadieu, B., Pittman Jr., C.U., Smith Jr., D.W. Triphenylene-Enchained Perfluorocyclobutyl (PFCB) Aryl Ether Polymers. A Modular Synthetic Route to Processable Thermoplastics Approaching Upper Limit Tg and Photostability. Macromolecules. 2021, 54, 16, 7666-7672.
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