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

doi:10.1002/anie.201907329

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

Chemistry

Research output: Contribution to journal › Article › peer-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, 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.

Original language	English (US)
Pages (from-to)	13778-13783
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	39
DOIs	https://doi.org/10.1002/anie.201907329
State	Published - Sep 23 2019

Keywords

macrocycles
nanoporous materials
radicals
self-assembly
solid-state structures

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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@article{235643d8b394469f9c4a9a9ec6636f3c,

title = "Cyclotris(paraquat-p-phenylenes)",

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.",

keywords = "macrocycles, nanoporous materials, radicals, self-assembly, solid-state structures",

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

note = "Funding Information: This research is part of the Joint Center of Excellence in Integrated Nano-Systems (JCIN) at King Abdulaziz City for Science and Technology (KACST) and Northwestern University (NU). The authors thank both KACST and NU for their continued support of this research. The contribution of the Integrated Molecular Structure Education and Research Center (IMSERC) at Northwestern University is also acknowledged gratefully. O.K.F. and L.R.R. are grateful for the financial support from the U.S. Department of Energy (DOE) Office of Science, Basic Energy Sciences Program (grant DE-FG02-08ER15967).",

year = "2019",

month = sep,

day = "23",

doi = "10.1002/anie.201907329",

language = "English (US)",

volume = "58",

pages = "13778--13783",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "39",

}

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.

In: Angewandte Chemie - International Edition, Vol. 58, No. 39, 23.09.2019, p. 13778-13783.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Cyclotris(paraquat-p-phenylenes)

AU - Anamimoghadam, Ommid

AU - Cooper, James A.

AU - Nguyen, Minh T.

AU - Guo, Qing Hui

AU - Mosca, Lorenzo

AU - Roy, Indranil

AU - Sun, Junling

AU - Stern, Charlotte L.

AU - Redfern, Louis

AU - Farha, Omar K.

AU - Stoddart, J. Fraser

N1 - Funding Information: This research is part of the Joint Center of Excellence in Integrated Nano-Systems (JCIN) at King Abdulaziz City for Science and Technology (KACST) and Northwestern University (NU). The authors thank both KACST and NU for their continued support of this research. The contribution of the Integrated Molecular Structure Education and Research Center (IMSERC) at Northwestern University is also acknowledged gratefully. O.K.F. and L.R.R. are grateful for the financial support from the U.S. Department of Energy (DOE) Office of Science, Basic Energy Sciences Program (grant DE-FG02-08ER15967).

PY - 2019/9/23

Y1 - 2019/9/23

N2 - 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.

AB - 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.

KW - macrocycles

KW - nanoporous materials

KW - radicals

KW - self-assembly

KW - solid-state structures

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U2 - 10.1002/anie.201907329

DO - 10.1002/anie.201907329

M3 - Article

C2 - 31338912

AN - SCOPUS:85071363012

VL - 58

SP - 13778

EP - 13783

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 39

ER -