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Chemistry of Anthracene–Acetylene Oligomers XX: Synthesis, Structures, and Self‐Association of Anthracene–Anthraquinone Cyclic Compounds with Ethynylene Linkers
Author(s) -
Iwanaga Tetsuo,
Miyamoto Kazuaki,
Tahara Kazukuni,
Inukai Koji,
Okuhata Satoshi,
Tobe Yoshito,
Toyota Shinji
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201101000
Subject(s) - anthracene , chemistry , moiety , sonogashira coupling , triptycene , dimer , acetylene , monomer , anthraquinone , steric effects , isopropyl , substituent , photochemistry , crystallography , polymer chemistry , stereochemistry , medicinal chemistry , organic chemistry , palladium , polymer , catalysis
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.