Greener Synthesis of Poly-1,3-Isobenzofurandione-4,7-diphenyl

Date
2018-04-15
Authors
Trainer, Nicholas
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Abstract
Poly(P-phenylene) is an organic polymer that has semiconductive properties. Organic semiconductors are becoming increasing utilized material in electronics nowadays due to them being a more environmentally friendly alternative to the standard inorganic semiconductors. This polymer will be synthesized via a Diels-Alder reaction between 1,4-diphenyl-1,3-butadiene and maleic anhydride followed by subsequent dehydroaromatization to the resulting terphenyl compound. A bromination will add functionality to the terphenyls to allow for an Ullman homocoupling or Suzuki polycondensation in order to form the desired polymer. The first reaction produced moderate yields (~60%) of 4,7-diphenyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione and a purification has been conducted to mostly remove the starting materials. The product has been oxidized using two different methods to provide minimal results. Further optimization must be conducted to the previous reactions to produce more significant yields before further steps are conducted. The remainder of the synthesis can then be conducted to finish synthesis of the polymer.
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Keywords
Polymers, Semiconductors, Molecules -- Models, Diels-Alder reaction
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