Synthesis, Properties, and Intermolecular Interactions in the Solid States of π-Congested X-Shaped 1,2,4,5-Tetra(9-anthryl)benzenes

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  • Tomohiko Nishiuchi
    Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043 , Japan
  • Shino Takeuchi
    Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043 , Japan
  • Yuta Makihara
    Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043 , Japan
  • Ryo Kimura
    Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa Oiwake, Sakyo, Kyoto 606-8502 , Japan
  • Shohei Saito
    Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa Oiwake, Sakyo, Kyoto 606-8502 , Japan
  • Hiroyasu Sato
    Rigaku Corporation, 3-9-12 Matsubara, Akishima, Tokyo 196-8666 , Japan
  • Takashi Kubo
    Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043 , Japan

説明

<jats:title>Abstract</jats:title> <jats:p>A Negishi coupling based synthesis of 1,2,4,5-tetra(9-anthryl)benzene derivatives, possessing X-shaped molecular structures, is described. The results of X-ray crystallographic analysis show that two-dimensional highly ordered packing structure of the crystalline state of the unsubstituted derivative is a consequence of intermolecular π-π and CH-π interactions between anthracene units. Photoirradiation of the unsubstituted derivative as a precipitated solution promotes intramolecular [4+4] photocycloaddition reactions between both adjacent pairs of anthracene units to produce a crystalline polycyclic product having a unique 1.700 Å long carbon-carbon single bond. Furthermore, charge-transfer complexes, displaying near-infrared absorption and emission, are generated by co-crystallization of the X-shaped unsubstituted member of the group with electron-acceptor molecules.</jats:p>

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