Cyclotris(paraquat-p-phenylenes)

Ommid Anamimoghadam*, James A. Cooper, Minh T. Nguyen, Qing Hui Guo, Lorenzo Mosca, Indranil Roy, Junling Sun, Charlotte L. Stern, Louis Redfern, Omar K. Farha, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Reported here is the synthesis, solid-state characterization, and redox properties of new triangular, threefold symmetric, viologen-containing macrocycles. Cyclotris(paraquat-p-phenylene) (CTPQT6+) and cyclotris(paraquat-p-1,4-dimethoxyphenylene) (MCTPQT6+) were prepared and their X-ray single-crystal (super)structures reveal intricate three-dimensional packing. MCTPQT6+ results in nanometer-sized channels, in contrast with its parent counterpart CTPQT6+ which crystallizes as a couple of polymorphs in the form of intercalated assemblies. In the solid state, MCTPQT3(.+) exhibits stacks between the 1,4-dimethoxyphenylene and bipyridinium radical cations, providing new opportunities for the manipulation and control of the recognition motif associated with viologen radical cations. These redox-active cyclophanes demonstrate that geometry-matching and weak intermolecular interactions are of paramount importance in dictating the formation of their intricate solid-state superstructures.

Original languageEnglish (US)
Pages (from-to)13778-13783
Number of pages6
JournalAngewandte Chemie - International Edition
Volume58
Issue number39
DOIs
StatePublished - Sep 23 2019

Keywords

  • macrocycles
  • nanoporous materials
  • radicals
  • self-assembly
  • solid-state structures

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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