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Symposium Year: 2012
Student(s): Erin Kennedy, Matthew Ellison, and Scott Riley
Faculty Mentor(s): Dr. Benjamin N. Norris
Efforts in the synthesis of furo[3,2,b]furan from the inexpensive compound isosorbide will be presented. Furo[3,2,b]furan has been identified as a promising monomer for the preparation of conducting polymers for organic photovoltaic (solar cell) applications. Furo[3,2,b]furan is a simple molecule with a formula of C6H4O2 and a planar bicyclic aromatic ring structure. The sulfur analog, thieno[3,2,b]thiophene is a well-known compound, but no reliable syntheses of furo[3,2,b]furan have been reported. Isosorbide serves as an ideal starting compound because 1) it already has the desired bicyclic carbon skeleton, and 2) it is inexpensive. A variety of procedures, including acid catalyzed dehydration and conversion of the alcohols to tosylates, has thus far been unsuccessful.
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