Perfluorocyclobutyl-Linked Hexa-<i>p</i><i>eri</i>-hexabenzocoronene Networks

Hexa-peri-hexabenzocoronene (HBC) derivatives possess many interesting properties ranging from liquid crystallinity, to hole transport, to variable emission behavior, yet are plagued by insolubility and general accessibility of polymerizable substituents. The first synthesis of trifluorovinyl ether-substituted hexabenzocoronene and its polymerization to perfluorocyclobutyl (PFCB) polymers and copolymers is shown. Unlike hydrocarbon ethers, fluoro vinyl ethers are stable under HBC oxidation conditions. Discrete HBC units in PFCB polymers provide access to potentially processable HBC optical materials.