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Synthesis and characterization of blue‐light emissive carbazole containing perfluorocyclobutyl arylene ether polymers
Authors:Kaizheng Zhu  Benjamin Lund  Rachel Stern  Stephen M Budy  Dennis W Smith Jr  Scott T Iacono
Institution:1. Department of Chemistry, University of Oslo, , N‐0315 Oslo, Norway;2. Department of Chemistry and The Alan G. MacDiarmid NanoTech Institute, The University of Texas at Dallas, , Richardson, Texas, 75080;3. Department of Chemistry and Chemistry Research Center, United States Air Force Academy, , Colorado, 80840
Abstract:A series of N‐alkyl/aryl carbazole 3,6‐substituted arylene trifluorovinyl ether (TFVE) monomers were synthesized in high purity and yield from a concise four‐step synthesis using carbazole as a starting material. Condensate‐free, step‐growth chain extension of the monomers afforded perfluorocyclobutyl (PFCB) arylene ether homo‐ and copolymers as solution processable, optically transparent blue‐light emissive materials. Arylene TFVE monomers and conversion to PFCB arylene ether polymers were structurally elucidated and purity confirmed by high resolution mass spectroscopy, NMR (1H, 13C, and 19F) spectroscopy, gel permeation chromatography, and attenuated total reflectance Fourier transform infrared analysis. Thermal analysis by differential scanning calorimetry and thermogravimetric analysis revealed glass transition temperatures >150 °C and onset of decomposition in nitrogen >410 °C with 40 wt % char yield up to 900 °C. Optical and electrochemical studies included solution (tetrahydrofuran) and solid state (spin cast thin film) UV–vis/fluorescence spectroscopy and cyclic voltammetry which showed structure dependence of these blue emissive systems on the nature of the N‐alkyl/aryl carbazole substitution in either homo‐ or copolymer configurations. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 552–560
Keywords:conjugated polymers  electrochemical  fluorescence  fluoropolymers  optics
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