Development and Application of Polycyclic Conjugated Systems Bearing a Pentalene Skeleton

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  • ペンタレン骨格を含む縮合多環状共役化合物の新規合成法の開発と応用
  • ペンタレン コッカク オ フクム シュクゴウ タカンジョウ キョウヤク カゴウブツ ノ シンキ ゴウセイホウ ノ カイハツ ト オウヨウ

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Recently, polycyclic conjugated systems bearing carbocyclic five-membered rings have attracted much attention because of their utility in organic electronic devices. Despite possessing a 4nπ electron periphery, dibenzopentalenes are fairly stable compounds with a planar structure. Thus, appropriate modification would provide them with desirable electronic properties. Recently we found novel reactions yielding dibenzopentalene derivatives from readily available o-bromoethynylbenzenes using commercially available nickel complexes, and from 2-bromotolans via a novel amino migration reaction. These methods are accessible to π-extended pentalene derivatives bearing various functional groups and aromatic ring systems. Among them, a dinaphthylpentalene derivative showed very high hole mobility (1.8×10−3 cm2V−1s−1) as amorphous materials. Furthermore, it was employed as a p-type material for organic heterojunction photovoltaic cells (PCE=0.94%, Voc=0.96 V). It is the first pentalene derivative for organic thin-film semiconductors.

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