Synthesis and spectral properties of poly(arylenevinylenes) incorporating 2-methoxy-5-(2′-ethylhexyloxy)-p-phenylene fragments in the polymer chain

We report the Wittig reactions of 2-methoxy-5-(2′-ethylhexyloxy)-1,4-xylylenebis(triphenylphosphonium bromide) with terephthalaldehyde, 1,4-naphthalenedicarbaldehyde and 9,10-anthracenedicarbaldehyde. Two sets of model compounds were synthesized. The first consisted of a central fragment of 2-methoxy-5-(2′-ethylhexyloxy)-p-phenylenevinylene straddled by two phenylvinyl, naphthylvinyl or anthrylvinyl units. The second set contained derivatives of distyrylbenzene, distyrylnaphthalene and distyrylanthracene with two methoxy groups in each styryl fragment. The photophysical behavior of the obtained polymers and model compounds was investigated through absorbance, excitation and fluorescence spectroscopy. The fluorescence excitation and emission spectra of solid solutions of poly [2-methoxy-5-(2′-ethylhexyloxy)-9,10-anthrylenevinylene] in poly(methyl methacrylate) films indicated that their photophysical properties are due to localized molecular interactions.