The fused-ring thieno[3,4-b]pyrazine (TP) unit has been demonstrated to be an excellent building block for the production of low band gap conjugated organic polymers. In 2008, the Rasmussen group published the synthesis of 2,3-bis(bromomethyl)thieno[3,4-b]pyrazine as a precursor to new TP analogues. Application of this precursor allows for the production of new tricyclic TPs incorporating furan and thiophene as the third fused ring. The synthesis of 1,3-dihydrofuro[3,4-e]thieno[3,4-b]pyrazine and 1,3-dihydrothieno[3,4-e]thieno[3,4-b]pyrazine will be presented, along with efforts to generate the aromatic analogues via dehydration. The full synthetic details and characterization of all new fused-ring thieno[3,4-b]pyrazine monomers will be presented, along with potential applications to conjugated polymeric materials.

Tricyclic nonclassical thiophenes: Synthesis of new fused-ring thiophene monomers and their application to conjugated materials

251st National Meeting (2016)

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