Synthesis and functionalization of a dibenzo-30-crown-10 derivative for incorporation into a light-emitting polymer

CHED 462

Erin E Fortin, efortin08@wooster.edu, Richard A. Giles, richarag@usc.edu, and Paul A. Bonvallet, pbonvallet@wooster.edu. Department of Chemistry, The College of Wooster, 943 College Mall, Wooster, OH 44691
This research combines ideas from polymer and supramolecular chemistry for potential use in organic light emitting diodes (OLEDs). The goal is to synthesize a crown ether-substituted polymer to color tune its photoluminescence as a supramolecular complex. Specifically, a dimethyl dibenzo-30-crown-10 derivative was synthesized from 4,5-dimethyl catechol and a ditosylate. TLC and 1H NMR confirmed the formation and relative purity of the desired product and a melting point was determined (64.7 – 69.3 °C). This compound was then converted to dibrominated dibenzo-30-crown-10 ether using NBS and light. The limited solubility of the brominated crown ether has influenced the synthesis of the desired phosphonate, the polymerization precursor. Upon characterization and purification, synthesis shall continue towards polymerizing the oligomer in order to produce the crown ether-substituted polymer similar to poly-p-phenylenevinylene (PPV).
 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008