Chemistry of Anthracene–Acetylene Oligomers XX: Synthesis,Structures, and Self-Association of Anthracene–Anthraquinone Cyclic Compounds with Ethynylene Linkers |
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| Authors: | Dr Tetsuo Iwanaga Kazuaki Miyamoto Dr Kazukuni Tahara Koji Inukai Satoshi Okuhata Prof?Dr Yoshito Tobe Prof?Dr Shinji Toyota |
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| Institution: | 1. Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005 (Japan), Fax: (+81)?256-9457;2. Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531 (Japan) |
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| Abstract: | We have synthesized anthracene–acetylene oligomers, which contained one 10-substituted anthracene unit and one anthraquinone unit, by cyclization with Sonogashira coupling. X-ray analysis revealed an almost-planar framework and significant out-of-plane deformation around the inner carbonyl moiety because of steric hindrance. These compounds underwent self-association in solution and their association constants for monomer–dimer exchange were determined by variable-concentration 1H NMR measurements in CDCl3: 8 mol?1 L (10-substituent: isopropyl), <5 mol?1 L (methoxy), and 19 mol?1 L (octyloxy). These results were discussed on the basis of spectroscopic and molecular-orbital analysis. A linear molecular assembly of the octyloxy compound at a liquid/graphite interface was observed by STM measurements. |
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| Keywords: | anthracenes acetylenes cross-coupling oligomerization self-assembly |
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