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 language | English (US) |
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Pages (from-to) | 13778-13783 |
Number of pages | 6 |
Journal | Angewandte Chemie - International Edition |
Volume | 58 |
Issue number | 39 |
DOIs | |
State | Published - Sep 23 2019 |
Keywords
- macrocycles
- nanoporous materials
- radicals
- self-assembly
- solid-state structures
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)