| 研究実績の概要 |
In this 2-years research project, firstly efficient chemistry was established to straightforwardly introduce alkylthio groups at the β-position of various thienoacenes, by utilizing new S-containing halogenoids as Larock electrophilic cyclization reaction. With the new chemistry a series of targeted thienoacene-based organic semiconductors were successfully developed.
The packing structures of the as-synthesized β-alkylthionated thienoacenes were studied by single-crystal X-ray diffraction (XRD) analysis. The study revealed that by attaching certain alkylthio groups (methylthio and 6-membered thiacycle) with the S atom connected to the β-position of linear thienoacenes, the corresponding crystal structures could be generally and selectively altered into the rubrene-like packing structure, in which efficient frontier orbital overlap could be realized. Theoretical calculation based on these materials illustrated that the generality and selectivity of this crystal structure engineering originated from a universal "disrupt and induce" manner of altering intermolecular interactions.
Single-crystal and thin-film organic field-effect transistors (OFETs) were fabricated based on the as-developed materials, and some of them showed excellent performance even rivaling rubrene.
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