Synthesis and characterization of novel poly(p-phenylenevinylene) derivatives containing phosphine oxide moiety

POLY 456

S. J. Yoon, tnqkr@gist.ac.kr, J. M. Ku, fawn83@gist.ac.kr, M. J. Yoon, peepin@gist.ac.kr, and Tae-Ho Yoon, thyoon@gist.ac.kr. Department of Materials Science and Engineering, Gwangju Institute of Science and Technology, 1, Oryong-dong, Buk-gu, Gwangju, 500-712, South Korea
Poly(2-methoxy-(5-(6'-dimethylphosphate)-hexyloxy)-1,4-phenylenevinylene-ran-2-methoxy-5-(2'-ethylhexyloxy)-1,4-phenyl-enevinylene) (MEH-PO-PPV) was synthesized via Heck coupling reaction from MEHOB-DV, MEHOB-2Br and MPOHOB-2Br by varying the ratio of MPOHOB-2Br and MEHOB-2Br (100/0, 60/40, 20/80, 0/100). The monomer, containing phosphine oxide groups, MPOHOB-2Br was synthesized via Williamson ether reaction from 4-methoxyphenol and 1,6-dibromohexane, followed by bromination and Arbuzov reaction with trimethyl phosphite, while MEHOB-2Br was synthesized via Williamson ether reaction from 4-methoxyphenol and 2-ethylhexyl bromide, followed by bromination. MEHOB-2Br was further reacted via formylation and subsequent Wittig reaction to afford MEHOB-DV. The monomers and their intermediates were analyzed by NMR, while the polymers were characterized by FT-IR, NMR, GPC, DSC, TGA, and solubility measurement, and optical (UV-vis, PL) and electrical properties (CV) were also evaluated. MEH-PO-PPV, containing phosphine oxide groups, exhibited better solubility, and blue shifting in UV-vis absorption and PL emission, compare with MEH-PPV