Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 47, Pages 16935-16940Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502848
Keywords
aggregation; dynamic covalent chemistry; macrocycles; olefin metathesis; pi interactions
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Funding
- Alfred P. Sloan Foundation
- Office of Energy Efficiency and Renewable Energy of the U.S. Department of Energy [DE-AC36-08GO28308]
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A series of phenylene vinylene macrocycles (PVMs) bearing substituents with various sizes and electronic properties have been synthesized through a one-step acyclic diene metathesis macrocyclization approach and their aggregation behaviors have been investigated. In great contrast to the aggregation of the analogous phenylene ethynylene macrocycles, which aggregate only when substituted with electron-withdrawing groups, these PVMs undergo exceptionally strong aggregation, regardless of the electron-donating or -withdrawing characters of the substituents. The unusual aggregation behavior of the PVMs is further investigated with thermodynamic and computer modeling studies, which show a good agreement with the recently proposed direct through-space interaction model, rather than the polar/pi model. The high aggregation tendency of PVMs suggests the great potential of this novel class of shape-persistent macrocycles in a variety of applications, such as ion channels, host-guest recognition, and catalysis.
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