Title: Covalent template approach toward functionalized oligo-alkyl-substituted shape-persistent macrocycles: Synthesis and properties of rings with a loop
Authors: Ziegler, A ×
Mamdouh, W
Heyen, AV
Surin, M
Ujii, Hiroshi
Abdel-Mottaleb, MMS
De Schryver, Frans
De Feyter, Steven
Lazzaroni, R
Hoger, S #
Issue Date: Nov-2005
Publisher: American Chemical Society
Series Title: Chemistry of Materials vol:17 issue:23 pages:5670-5683
Abstract: The synthesis, properties, and conformation of shape-persistent macrocycles with extraannular oligoalkyl groups and an intraannular bis(hydroxymethyl)biphenylene diester are investigated. The key step in the preparation is the template-supported Glaser coupling of rigid bisacetylenes which allows obtaining the cyclic product in 81 % yield. Contrary to the initial expectations, the compounds do not exhibit liquid crystalline phases. This could be explained by a nonplanar conformation of the molecules because the biphenylene bridge is longer than the diameter of the rings. On the other hand, scanning tunneling microscopy investigations indicate that the intraannular biphenylene bridge can be located in the same plane as the aromatic backbone of the macrocycles on graphite. Modeling involving molecular mechanics and molecular dynamics simulations unraveled this apparent inconsistency by showing that the molecules adopt a nonplanar conformation in the absence of the solid support whereas planarization takes place when they are adsorbed on the graphite surface.
ISSN: 0897-4756
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Imaging and Photonics
× corresponding author
# (joint) last author

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