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 (1)H NMR measurements in CDCl(3): 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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Chemistry of Anthracene-Acetylene Oligomers XXVII. Iterative Synthesis, Structures, and Properties of Anthracene-Diacetylene Cyclic Oligomers with 10-Mesitylanthracene-1,8-diyl Units.
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Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan.
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 (1)H NMR measurements in CDCl(3): 8 mol(-1) L (10-substituent: isopropyl), <5 mol(-1) L (methoxy), and 19 mol(-1) L (octyloxy).
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Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan.
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March 2006
Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700-0005, Japan.
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