Received August 6, 2007

Revised Manuscript Received October 5, 2007

Abstract:

Versatile intermediates 4-bromo(trifluorovinyloxy)benzene or 4-trifluorovinyloxyphenylboronic acid pinacol ester undergo a one step Suzuki coupling reaction with commercial aryl diboronic acids or aryl dibromides and afforded three new aryltrifluorovinylether chromophore monomers. The structures of these monomers were confirmed by ¹H, ¹⁹F, and ¹³C NMR spectroscopy and elemental (C, H, and N) combustion analysis. The monomers were readily polymerized via thermal [2 + 2] cyclopolymerization to form chromophore containing PFCB polymers with high molecular weights (Mn = 16 700-22 000), superb thermal stability T_d > 450 C, and excellent processability. Photoluminescence studies reveal that the fluorinated ether linkage has no effect on lumiphore emission wavelength or solution quantum yields. Copolymerization affords a facile route to tailored emission from a linear polymeric system that includes a broad range of the visible spectrum. The properties of these polymers were analyzed by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), gel permeation chromatography (GPC), and absorbance and photoluminescence spectroscopy.

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