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Cyclotris(paraquat-p-phenylenes).

Ommid Anamimoghadam¹, James A Cooper¹, Minh T Nguyen¹

¹Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL, 60208, USA.

Angewandte Chemie (International Ed. in English)

|July 25, 2019

Summary

New triangular macrocycles containing viologen units were synthesized and characterized. Their solid-state structures reveal unique packing and nanometer-sized channels, offering control over viologen radical cation interactions.

Keywords:

macrocycles nanoporous materials radicals self-assembly solid-state structures

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Area of Science:

Supramolecular Chemistry
Materials Science
Organic Synthesis

Background:

Viologen-containing macrocycles are of interest for their redox properties and potential applications.
Understanding the relationship between molecular structure and solid-state packing is crucial for materials design.

Purpose of the Study:

To synthesize and characterize novel triangular, threefold symmetric, viologen-containing macrocycles.
To investigate the solid-state structures and redox properties of these new compounds.
To explore the influence of molecular geometry and intermolecular interactions on superstructure formation.

Main Methods:

Synthesis of cyclotris(paraquat-p-phenylene) (CTPQT⁶⁺) and cyclotris(paraquat-p-1,4-dimethoxyphenylene) (MCTPQT⁶⁺).
X-ray single-crystal structure determination to analyze three-dimensional packing.
Solid-state characterization and redox property analysis.

Main Results:

CTPQT⁶⁺ and MCTPQT⁶⁺ were successfully synthesized.
X-ray crystallography revealed intricate 3D packing, with MCTPQT⁶⁺ forming nanometer-sized channels.
MCTPQT^3(.+) demonstrated stacking between aromatic components and radical cations, enabling control over recognition motifs.

Conclusions:

The synthesized viologen macrocycles exhibit complex solid-state superstructures dictated by geometry and weak interactions.
MCTPQT⁶⁺ offers new possibilities for manipulating viologen radical cation recognition in the solid state.
This work highlights the importance of supramolecular assembly in designing functional organic materials.