Synthesis of Regioregular Poly(p-phenylenevinylene)s by Horner Reaction and Their Regioregularity Characterization

A new synthetic route was developed to obtain highly regioregular poly[(2-methoxy-5-alkyloxy)-1,4-phenylenevinylene]s (PPVs) by the Horner reaction using asymmetrically functionalized monomers. The polymers showed good solubility in chlorobenzene at over 100 C. The high regioregularity of the polymers was confirmed by ¹H NMR quantitative analysis using chlorobenzene-d₅ as solvent, which was developed for the first time in this study. Assignment of the ¹H NMR peaks was conducted by synthesizing four novel model compounds for PPV. UV-vis, fluorescence spectra, and XRD data revealed that these regioregular PPVs have higher crystallinity compared to regiorandom PPVs in the solid state.

Macromolecules, 40 (18), 6521 -6528, 2007. 10.1021/ma0628836