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Zhang C, Yu C, Long H, et al. Synthesis of Phenylene Vinylene Macrocycles through Acyclic Diene Metathesis Macrocyclization and Their Aggregation Behavior. Chemistry. 2015;21(47):16935-40doi: 10.1002/chem.201502848.
Zhang, C., Yu, C., Long, H., Denman, R. J., Jin, Y., & Zhang, W. (2015). Synthesis of Phenylene Vinylene Macrocycles through Acyclic Diene Metathesis Macrocyclization and Their Aggregation Behavior. Chemistry (Weinheim an der Bergstrasse, Germany), 21(47), 16935-40. https://doi.org/10.1002/chem.201502848
Zhang, Chenxi, et al. "Synthesis of Phenylene Vinylene Macrocycles through Acyclic Diene Metathesis Macrocyclization and Their Aggregation Behavior." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,47 (2015): 16935-40. doi: https://doi.org/10.1002/chem.201502848
Zhang C, Yu C, Long H, Denman RJ, Jin Y, Zhang W. Synthesis of Phenylene Vinylene Macrocycles through Acyclic Diene Metathesis Macrocyclization and Their Aggregation Behavior. Chemistry. 2015 Nov 16;21(47):16935-40. doi: 10.1002/chem.201502848. Epub 2015 Sep 30. PMID: 26420443.
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Chemistry. 2015 Nov 16;21(47):16935-40. doi: 10.1002/chem.201502848. Epub 2015 Sep 30.

Synthesis of Phenylene Vinylene Macrocycles through Acyclic Diene Metathesis Macrocyclization and Their Aggregation Behavior.

Chemistry (Weinheim an der Bergstrasse, Germany)

Chenxi Zhang, Chao Yu, Hai Long, Ryan J Denman, Yinghua Jin, Wei Zhang

Affiliations

  1. Department of Chemistry and Biochemistry, University of Colorado Boulder, Boulder, Colorado, 80309 (USA).
  2. National Renewable Energy Laboratory, Golden, Colorado 80401 (USA).
  3. Department of Chemistry and Biochemistry, University of Colorado Boulder, Boulder, Colorado, 80309 (USA). [email protected].
  4. Department of Chemistry and Biochemistry, University of Colorado Boulder, Boulder, Colorado, 80309 (USA). [email protected].

PMID: 26420443 DOI: 10.1002/chem.201502848

Abstract

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/π 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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: aggregation; dynamic covalent chemistry; macrocycles; olefin metathesis; π interactions

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