Synthesis and Characterization of Novel PPV Derivatives

Abstract

Five kinds of poly(phenylene vinylene) (PPV) derivatives with different alkoxyl substituents were synthesized with optimized synthesis procedures. The optimized PPV derivatives are reacted at 80°C for 6 h after mixing of the reactants at 45°C, and then followed by aging at 95°C for 1 h. The optimized molar ratios of dichlorobenzyl chloride/potassium tert-butoxide for poly(2-methoxy-5-butoxy)-p-phenylene vinylene and poly(2,5-dibutyloxy)- 1,4-phenylene vinylene are 1/7 and 1/8, respectively. The yields of the derivatives increased gradually with the chain length of the substituents; however, the yields decreased with a further increase in the chain length to an eight-carbon substituent, which is resulted from the counteraction of the electronic effect by the steric effect of the substituents. The solubility of the derivatives was greatly enhanced with the incorporation of the alkoxyl substituents, and the highest solubility of 3.08% in chloroform and 1.79% in tetrahydrofuran is demonstrated by poly(2-methoxy-5-octyloxy)-p-phenylene vinylene (PMOOOPV). All derivatives exhibited higher solubility in chloroform than in tetrahydrofuran. The conductivity of the derivatives increased with increasing of the substituting chain lengths as a result of the enhanced the conjugation degree and lowered energy gap, and the highest conductivity of 2.9 × 10−4 S/cm was exhibited by PMOOOPV. © 2012 Wiley Periodicals, Inc. Adv Polym Techn 32: E603–E611, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/adv.21304