Synthesis of the Soluble Precursors of Tetrabenzoporphyrins and Their Application to Organic Field Effect Transistor Based on the Solution Process

Alkyl-substituted and small-ring-fused bicyclo[2.2.2]octadiene (BCOD) fused porphyrins were synthesized by tetramerization method of the corresponding BCOD-fused pyrroles, which were obtained by the Diels–Alder reaction of trans-1,2-bis(phenylsulfonyl)ethylene with the appropriate 1,3-cyclohexadienes, followed by the Barton–Zard reaction. These soluble precursors were converted into tetrabenzoporphyrin (TBP) by heating at 180–230 °C depending on the structure of BCOD moiety. Organic field effect transistors based on TBP were fabricated by thermal conversion after spin-coating of the precursors to show good carrier mobility of 10⁻⁶–10⁰ cm² V⁻¹ s⁻¹.