Synthesis of 1-butoxy-2,5-dicarboethoxy-3,4-diphenylbenzene

Abstract

<p>The terephthalate, 1-butoxy-2,S-dicarboethoxy3,4-diphenylbenzene is an important synthetic precursor to monomers which can be polymerized to form substituted poly{phenylene vinylene)s. Poly{phenylene vinylene)s are capable of electroluminescence and have been used as the emissive layer in organic light emitting diodes. The terephthalate molecule was synthesized with phenyl substituents and a long side chain to allow for increased polymer solubility, and color tunability1,2. Ethynylboronic acid Nmethyliminodiacetic acid ester has been a useful tool in the synthesis of 1-butoxy-2,Sdicarboethoxy-3,4-diphenylbenzene in that it both reacts readily to form the boronate protected terephthalate which is easily oxidized to form the phenolic compound, both in good yields. The phenol can then be butylated to form the desired product. This research focuses on the synthesis and identification of multisubstituted terephthalates using 1H NMR and 13C NMR.</p><p>This presentation occurred at the Wright State University Campus-Wide Celebration of Research, Scholarship and Creative Activities on April 16, 2010</p>