title: Chemistry of anthracene-acetylene oligomers XX: synthesis, structures, and self-association of anthracene-anthraquinone cyclic compounds with ethynylene linkers.
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 (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.
authors.affiliation: Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan.
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Iwanaga
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Miyamoto
authors.forename: Kazukuni
authors.initials: K
authors.lastname: Tahara
authors.forename: Koji
authors.initials: K
authors.lastname: Inukai
authors.forename: Satoshi
authors.initials: S
authors.lastname: Okuhata
authors.forename: Yoshito
authors.initials: Y
authors.lastname: Tobe
authors.forename: Shinji
authors.initials: S
authors.lastname: Toyota