Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, 4259, Nagatsuta, Midori-ku, Yokohama 226-8502, Japan.
Chemistry. 2012 Jul 16;18(29):8964-70. doi: 10.1002/chem.201200591. Epub 2012 Jun 12.
Fused polycyclic indeno[1,2-b]fluorene derivatives with aryl substituents at the 6,12-positions have been prepared as a potential antiaromatic 20π electronic system. They showed strong absorptions in the visible region and amphoteric redox properties. The quinoid-type molecular structures were revealed by X-ray crystal-structure analysis, which indicated that the bond lengths of the quinoid unit depend on the aryl substituents. Whereas nucleus-independent chemical shift NICS(1) calculations indicate the antiaromatic nature of the s-indacene core, they have higher stability than substituted acene derivatives. The derivatives with difluorophenyl or anthryl groups were stable in solution. Vapor-deposited thin films showed ambipolar carrier transportation in the field-effect transistor devices.
具有芳基取代基的稠合多环茚并[1,2-b]芴衍生物已被制备为潜在的反芳香 20π 电子体系。它们在可见光区表现出强烈的吸收，并具有两性氧化还原性质。X 射线晶体结构分析揭示了醌型分子结构，表明醌单元的键长取决于芳基取代基。而核独立化学位移 NICS(1)计算表明 s-茚并核具有反芳香性质，但它们比取代的薁衍生物更稳定。具有二氟苯基或蒽基的衍生物在溶液中稳定。真空沉积的薄膜在场效应晶体管器件中表现出双极性载流子输运。
