Cyclotris(paraquat‐ p ‐phenylenes)

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

doi:10.1002/ange.201907329

Title: Cyclotris(paraquat‐ p ‐phenylenes)

Journal Article · 29 August 2019 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.201907329 · OSTI ID:1559396

^[1]; Cooper, James A. ^[1]; Nguyen, Minh T. ^[1]; Guo, Qing‐Hui ^[1]; Mosca, Lorenzo ^[1]; Roy, Indranil ^[1]; Sun, Junling ^[1]; Stern, Charlotte L. ^[1]; Redfern, Louis ^[1]; Farha, Omar K. ^[1]; Stoddart, J. Fraser ^[2]

Department of Chemistry Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
Department of Chemistry Northwestern University 2145 Sheridan Road Evanston IL 60208 USA, Institute for Molecular Design and Synthesis Tianjin University 92 Weijin Road Tianjin 300072 China, School of Chemistry University of New South Wales Sydney NSW 2052 Australia

Abstract Reported here is the synthesis, solid‐state characterization, and redox properties of new triangular, threefold symmetric, viologen‐containing macrocycles. Cyclotris(paraquat‐ p ‐phenylene) ( CTPQT ⁶⁺ ) and cyclotris(paraquat‐ p ‐1,4‐dimethoxyphenylene) ( MCTPQT ⁶⁺ ) were prepared and their X‐ray single‐crystal (super)structures reveal intricate three‐dimensional packing. MCTPQT ⁶⁺ results in nanometer‐sized channels, in contrast with its parent counterpart CTPQT ⁶⁺ which crystallizes as a couple of polymorphs in the form of intercalated assemblies. In the solid state, MCTPQT ^3(.+) 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.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; FG02-08ER15967

OSTI ID:: 1559396

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 39 Vol. 131; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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