Synthesis and characterization of highly fluorescent phenylene vinylene containing perfluorocyclobutyl (PFCB) aromatic ether polymers

摘要

4-(Trifluorovinyloxy)benzaldehyde was treated under Wittig conditions with 4-dihexyloxy-2,5-xylene-bis(triphenylphosphoniumbromide) to form 1,4-bis(2'-(4-trifluorovinyloxyphenyl)ethenyl)-2,5-dihexyloxybenzene, a novel phenylene vinylene-bistrifluorovinyl ether monomer. Cyclopolymerization afforded an insoluble, non-luminescent material likely due to cross-addition reactions between phenylene vinylene olefin and trifluorovinyl ether (TFVE). However, 1,2-bis(4-formylphenoxy)hexafluorocyclobutane was polymerized with 1,4-dihexyloxy-2,5-xylenebis(triphenylphosphoniumbromide) and 1-methoxy-4-(2-ethyl hexyloxy)-2,5-xylenebis(triphenylphosphoniumbromide) under Wittig conditions to yield two novel poly(perfluorocyclobutyl-co-phenylene vinylene) polymers. The polymers are of moderate molecular weight (8600-8700 M-n), show excellent thermal stability (T-d = 390-405 degrees C), and are readily soluble in common organic solvents. The materials are highly fluorescent in both solution and thin film with solution quantum yields of 68 and 71%. (C) 2008 Elsevier Ltd. All rights reserved.