Triphenylene-Enchained Perfluorocyclobutyl Aryl Ether Polymers: A Modular Synthetic Route to Processable Thermoplastics Approaching Upper Limit T g and Photostability

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Triphenylene-containing trifluorovinyl ether monomers prepared from 2,3-disubstituted- bis -1,4-( p -bromophenyl)triphenylene core building blocks undergo thermal step-growth polymerization (Ph 2 O, 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 (λ em = ∼400–470 nm). Conversion was monitored by 19 F NMR end-group analysis and gel permeation chromatography to reasonably high molecular weights ( M n = 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.