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
- Chemistry(all)
- Catalysis
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CCDC 1914256: Experimental Crystal Structure Determination
Anamimoghadam, O. (Contributor), Cooper, J. A. (Contributor), Nguyen, M. T. (Contributor), Guo, Q. (Contributor), Mosca, L. (Contributor), Roy, I. (Contributor), Sun, J. (Contributor), Stern, C. L. (Contributor), Redfern, L. (Contributor), Farha, O. K. (Contributor) & Stoddart, J. F. (Contributor), Cambridge Crystallographic Data Centre, 2019
DOI: 10.5517/ccdc.csd.cc227y6h, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc227y6h&sid=DataCite
Dataset
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CCDC 1914255: Experimental Crystal Structure Determination
Anamimoghadam, O. (Contributor), Cooper, J. A. (Contributor), Nguyen, M. T. (Contributor), Guo, Q. (Contributor), Mosca, L. (Contributor), Roy, I. (Contributor), Sun, J. (Contributor), Stern, C. L. (Contributor), Redfern, L. (Contributor), Farha, O. K. (Contributor) & Stoddart, J. F. (Contributor), Cambridge Crystallographic Data Centre, 2019
DOI: 10.5517/ccdc.csd.cc227y5g, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc227y5g&sid=DataCite
Dataset
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CCDC 1914249: Experimental Crystal Structure Determination
Anamimoghadam, O. (Contributor), Cooper, J. A. (Contributor), Nguyen, M. T. (Contributor), Guo, Q. (Contributor), Mosca, L. (Contributor), Roy, I. (Contributor), Sun, J. (Contributor), Stern, C. L. (Contributor), Redfern, L. (Contributor), Farha, O. K. (Contributor) & Stoddart, J. F. (Contributor), Cambridge Crystallographic Data Centre, 2019
DOI: 10.5517/ccdc.csd.cc227xz7, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc227xz7&sid=DataCite
Dataset