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

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

Research output: Contribution to journalArticlepeer-review

13 Scopus Citations

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.

Original languageAmerican English
Pages (from-to)16935-16940
Number of pages6
JournalChemistry - A European Journal
Volume21
Issue number47
DOIs
StatePublished - 2015

Bibliographical note

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

NREL Publication Number

  • NREL/JA-2C00-65581

Keywords

  • aggregation
  • dynamic covalent chemistry
  • macrocycles
  • olefin metathesis
  • π interactions

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