Chemistry of anthracene-acetylene oligomers XX: synthesis, structures, and self-association of anthracene-anthraquinone cyclic compounds with ethynylene linkers.
Chem Asian J
; 7(5): 935-43, 2012 May.
Article
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| MEDLINE
| ID: mdl-22345052
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.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Tipo de estudio:
Risk_factors_studies
Idioma:
En
Revista:
Chem Asian J
Año:
2012
Tipo del documento:
Article
País de afiliación:
Japón