CHED 596 |
| The goal of this project was to prepare a high molecular weight photoluminescent polymer from a benzodioxole-containing monomer. In contrast to the frequently used Wittig reaction, the Horner-Wadsworth-Emmons reaction is typically better at providing an all-trans geometry and avoids the formation of triphenylphosphine oxide. The diphosphonate precursor was prepared from 1,3-benzodioxole in 42% overall yield and was characterized by 1H, 13C, and 31P NMR spectroscopy. Reaction of the diphosphonate with sodium methoxide followed by terephthalaldehyde produced a yellow powder characterized by NMR spectroscopy and gel permeation chromatography (Mw = 649, Mn = 482). The material is of surprisingly low molecular weight and is not photoluminescent. If the material is to be used in the creation of an organic light-emitting diode, its molecular mass and emissive properties will need to be improved.
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Chemical Education |
