Oligothiophene quinoids containing a benzo[: C] thiophene unit for the stabilization of the quinoidal electronic structure
Bis(dicyanomethylene)-substituted quinoidal π-conjugated systems possess a high electron-accepting nature and thus have been extensively investigated for application as n-type semiconductors. We focus on the utilization of benzene-annelation for the stabilization of the quinoidal electronic structure against the biradicaloid structure by designing quinoidal thiophenes 3-mer (BTQ) and 6-mer (BTQ-6) that have benzo[c]thiophene units. We also develop quinoidal oligothiophenes (BTQ-F) consisting of both benzo[c]thiophene and fluorinated thiophene units. The influence of benzo[c]thiophene on the quinoidal electronic structure is investigated by theoretical studies and property measurements. The molecular structure of BTQ-F is unambiguously confirmed through single-crystal X-ray diffraction. Analyses of cyclic voltammetry reveal that the lowest unoccupied molecular orbital energy levels of these compounds lie below -4.0 eV, leading to good electron-transporting characteristics even under ambient conditions in organic field-effect transistors (OFETs). Due to an increased highest occupied molecular orbital energy level, ambipolar transport is observed in BTQ-6, indicating the versatility of quinoidal π-conjugated systems incorporating benzo[c]thiophene.
Yamamoto, Keitaro,Ie, Yutaka,Nitani, Masashi,Tohnai, Norimitsu,Kakiuchi, Fumitoshi,Zhang, Ke,Pisula, Wojciech,Asadi, Kamal,Blom, Paul W. M.,Aso, Yoshio
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p. 7493 - 7500
(2018/07/29)
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