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Issue 5, 2011
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Synthesis and properties of a triphenylene–butadiynylenemacrocycle

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Abstract

The synthesis and characterization of a shape-persistent triphenylenebutadiynylene macrocycle formed by intermolecular Glaser-coupling of two “half-rings” and also by intramolecular coupling of the appropriate open dimer, respectively, are described in detail. The investigation of the photophysics has revealed that—compared to its open dimer—the macrocycle is more conjugated in the ground state and less so in the excited state, a result of the diacetylene bending in the macrocycle due to its constrained topology. The macrocycle is decorated with flexible side groups that support its adsorption on highly oriented pyrolytic graphite (HOPG) where a concentration-dependence of the 2D-structure is observed by means of scanning tunnelling microscopy (STM). The flexible side groups also guarantee a high compound solubility even in nonpolar solvents (cyclohexane). However, solvophobic interactions lead to the formation of a tube-like superstructure, as revealed by dynamic light scattering, X-ray scattering and atomic force microscopy.

Graphical abstract: Synthesis and properties of a triphenylene–butadiynylene macrocycle

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Supplementary files

Article information


Submitted
06 Jul 2010
Accepted
23 Aug 2010
First published
22 Sep 2010

J. Mater. Chem., 2011,21, 1404-1415
Article type
Paper

Synthesis and properties of a triphenylenebutadiynylene macrocycle

H. Wettach, S. Höger, D. Chaudhuri, John. M. Lupton, F. Liu, E. M. Lupton, S. Tretiak, G. Wang, M. Li, S. De Feyter, S. Fischer and S. Förster, J. Mater. Chem., 2011, 21, 1404
DOI: 10.1039/C0JM02150D

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