Cyclotris(paraquat‐ p ‐phenylenes)
Abstract
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.
- Authors:
-
[1];
- 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
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1559396
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Angewandte Chemie
- Additional Journal Information:
- Journal Name: Angewandte Chemie Journal Volume: 131 Journal Issue: 39; Journal ID: ISSN 0044-8249
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
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., and Stoddart, J. Fraser. Cyclotris(paraquat‐ p ‐phenylenes). Germany: N. p., 2019.
Web. doi:10.1002/ange.201907329.
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. Cyclotris(paraquat‐ p ‐phenylenes). Germany. https://doi.org/10.1002/ange.201907329
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., and Stoddart, J. Fraser. Thu .
"Cyclotris(paraquat‐ p ‐phenylenes)". Germany. https://doi.org/10.1002/ange.201907329.
@article{osti_1559396,
title = {Cyclotris(paraquat‐ p ‐phenylenes)},
author = {Anamimoghadam, Ommid and Cooper, James A. and Nguyen, Minh T. and Guo, Qing‐Hui and Mosca, Lorenzo and Roy, Indranil and Sun, Junling and Stern, Charlotte L. and Redfern, Louis and Farha, Omar K. and Stoddart, J. Fraser},
abstractNote = {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.},
doi = {10.1002/ange.201907329},
journal = {Angewandte Chemie},
number = 39,
volume = 131,
place = {Germany},
year = {Thu Aug 29 00:00:00 EDT 2019},
month = {Thu Aug 29 00:00:00 EDT 2019}
}
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1002/ange.201907329
https://doi.org/10.1002/ange.201907329
Other availability
Search WorldCat to find libraries that may hold this journal
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis
journal, November 1995
- Desiraju, Gautam R.
- Angewandte Chemie International Edition in English, Vol. 34, Issue 21
Cucurbit[n]uril-based coordination chemistry: from simple coordination complexes to novel poly-dimensional coordination polymers
journal, January 2013
- Ni, Xin-Long; Xiao, Xin; Cong, Hang
- Chemical Society Reviews, Vol. 42, Issue 24
Well-Rounded Research: Nanotubes through Self-Assembly
journal, September 1997
- König, Burkhard
- Angewandte Chemie International Edition in English, Vol. 36, Issue 17
Cyclophanes within Cyclophanes: The Synthesis of a Pyromellitic Diimide-Based Macrocycle as a Structural Unit in a Molecular Tube and Its Inclusion Phenomena
journal, May 2006
- Iwanaga, Tetsuo; Nakamoto, Ryoma; Yasutake, Mikio
- Angewandte Chemie, Vol. 118, Issue 22
A Boat-Shaped Tetracationic Macrocycle with a Semiconducting Organic Framework
journal, April 2017
- Nguyen, Minh T.; Krzyaniak, Matthew D.; Owczarek, Magdalena
- Angewandte Chemie, Vol. 129, Issue 21
Engineering discrete stacks of aromatic molecules
journal, January 2009
- Klosterman, Jeremy K.; Yamauchi, Yoshihiro; Fujita, Makoto
- Chemical Society Reviews, Vol. 38, Issue 6
Supramolekulare Chemie – Moleküle, Übermoleküle und molekulare Funktionseinheiten (Nobel-Vortrag)
journal, January 1988
- Lehn, Jean-Marie
- Angewandte Chemie, Vol. 100, Issue 1
Pillararenes, A New Class of Macrocycles for Supramolecular Chemistry
journal, May 2012
- Xue, Min; Yang, Yong; Chi, Xiaodong
- Accounts of Chemical Research, Vol. 45, Issue 8
Spin Frustration in the Triradical Trianion of a Naphthalenediimide Molecular Triangle
journal, February 2017
- Wu, Yilei; Krzyaniak, Matthew D.; Stoddart, J. Fraser
- Journal of the American Chemical Society, Vol. 139, Issue 8
Solution-Phase Mechanistic Study and Solid-State Structure of a Tris(bipyridinium radical cation) Inclusion Complex
journal, February 2012
- Fahrenbach, Albert C.; Barnes, Jonathan C.; Lanfranchi, Don Antoine
- Journal of the American Chemical Society, Vol. 134, Issue 6
Synthetic Cyclic Oligosaccharides-Syntheses and Structural Properties of a Cyclo[(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-α-D-mannopyranosyl]trioside and -tetraoside
journal, May 1996
- Ashton, Peter R.; Brown, Christopher L.; Menzer, Stephan
- Chemistry - A European Journal, Vol. 2, Issue 5
Calixarenenanotubes: structural tolerance towards pyridine templates
journal, January 2011
- Kennedy, Stuart; Beavers, Christine M.; Teat, Simon J.
- New J. Chem., Vol. 35, Issue 1
The Viologen Cation Radical Pimer: A Case of Dispersion-Driven Bonding
journal, July 2017
- Geraskina, Margarita R.; Dutton, Andrew S.; Juetten, Mark J.
- Angewandte Chemie, Vol. 129, Issue 32
Metal-Organic Calixarene Nanotubes
journal, May 2010
- Kennedy, Stuart; Karotsis, Georgios; Beavers, Christine M.
- Angewandte Chemie, Vol. 122, Issue 25
Amino-Functionalized Pillar[5]arene
journal, July 2014
- Strutt, Nathan L.; Zhang, Huacheng; Schneebeli, Severin T.
- Chemistry - A European Journal, Vol. 20, Issue 35
The Cucurbit[n]uril Family
journal, August 2005
- Lagona, Jason; Mukhopadhyay, Pritam; Chakrabarti, Sriparna
- Angewandte Chemie International Edition, Vol. 44, Issue 31, p. 4844-4870
Assembled Columnar Structures from bis-urea Macrocycles
journal, January 2005
- Shimizu, Linda S.; Hughes, Andrew D.; Smith, Mark D.
- Supramolecular Chemistry, Vol. 17, Issue 1-2
Eine runde Sache: Nanoröhren durch Selbstanordnung
journal, September 1997
- König, Burkhard
- Angewandte Chemie, Vol. 109, Issue 17
Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices(Nobel Lecture)
journal, January 1988
- Lehn, Jean-Marie
- Angewandte Chemie International Edition in English, Vol. 27, Issue 1
The Viologen Cation Radical Pimer: A Case of Dispersion-Driven Bonding
journal, July 2017
- Geraskina, Margarita R.; Dutton, Andrew S.; Juetten, Mark J.
- Angewandte Chemie International Edition, Vol. 56, Issue 32
Cucurbituril
journal, December 1981
- Freeman, W. A.; Mock, W. L.; Shih, N. Y.
- Journal of the American Chemical Society, Vol. 103, Issue 24
Cyclophanes with self-recognising components
journal, January 1995
- Anelli, Pier-Lucio; Asakawa, Masumi; Ashton, Peter R.
- Journal of the Chemical Society, Chemical Communications, Issue 24
Isolation and oxidation-reduction of methylviologen cation radicals. Novel disproportionation in charge-transfer salts by x-ray crystallography
journal, June 1990
- Bockman, T. M.; Kochi, J. K.
- The Journal of Organic Chemistry, Vol. 55, Issue 13, p. 4127-4135
Redox Control of the Binding Modes of an Organic Receptor
journal, August 2015
- Frasconi, Marco; Fernando, Isurika R.; Wu, Yilei
- Journal of the American Chemical Society, Vol. 137, Issue 34
Catenane: fünfzig Jahre molekulare Verschlingungen
journal, May 2015
- Gil-Ramírez, Guzmán; Leigh, David A.; Stephens, Alexander J.
- Angewandte Chemie, Vol. 127, Issue 21
A World Beyond Hydrogen Bonds?—Chalcogen–Chalcogen Interactions Yielding Tubular Structures
journal, June 2003
- Gleiter, Rolf; Werz, Daniel B.; Rausch, Bernhard J.
- Chemistry - A European Journal, Vol. 9, Issue 12
Metal-Organic Calixarene Nanotubes
journal, May 2010
- Kennedy, Stuart; Karotsis, Georgios; Beavers, Christine M.
- Angewandte Chemie International Edition, Vol. 49, Issue 25
Self-complementary Tetracationic Cyclophanes Containing 4,4′-Bipyridinium and 2,5-Dimethoxy-1,4-xylyl Subunits
journal, April 2005
- Srinivasan, Kannupal; Rajakumar, Perumal
- Supramolecular Chemistry, Vol. 17, Issue 3
Toward artificial ion channels: self-assembled nanotubes from calix[4]arene–guanosine conjugates
journal, January 2000
- Sidorov, Vladimir; Kotch, Frank W.; Davis, Jeffery T.
- Chemical Communications, Issue 23
A self-organised layered superstructure of arrayed [2]pseudorotaxanes
journal, January 1994
- Ashton, Peter R.; Philp, Douglas; Spencer, Neil
- Journal of the Chemical Society, Chemical Communications, Issue 2
Die Cucurbit[n]uril-Familie
journal, August 2005
- Lagona, Jason; Mukhopadhyay, Pritam; Chakrabarti, Sriparna
- Angewandte Chemie, Vol. 117, Issue 31
Molekulare Mosaiken – ein quadratisches Cyclophan und sein Einschlußkomplex mit Ferrocen
journal, September 1995
- Ashton, Peter R.; Claessens, Christian G.; Hayes, Wayne
- Angewandte Chemie, Vol. 107, Issue 17
Self-Assembled Phenylethynylene Bis-urea Macrocycles Facilitate the Selective Photodimerization of Coumarin
journal, May 2011
- Dawn, Sandipan; Dewal, Mahender B.; Sobransingh, David
- Journal of the American Chemical Society, Vol. 133, Issue 18
Carbothdrate Nanotubes
journal, August 1997
- Gattuso, Giuseppe; Menzer, Stephan; Nepogodiev, Sergey A.
- Angewandte Chemie International Edition in English, Vol. 36, Issue 1314
Self-Assembly and Self-Organization of Self-Recognizing Cyclophanes
journal, June 1998
- Ashton, Peter R.; Chemin, Alexandre; Claessens, Christian G.
- European Journal of Organic Chemistry, Vol. 1998, Issue 6
Organische Nanoröhren durch Selbstorganisation
journal, March 2001
- Bong, Dennis T.; Clark, Thomas D.; Granja, Juan R.
- Angewandte Chemie, Vol. 113, Issue 6
Self-Assembling Organic Nanotubes from Enantiopure Cyclo-N,N′-Linked Oligoureas: Design, Synthesis, and Crystal Structure
journal, June 2002
- Semetey, Vincent; Didierjean, Claude; Briand, Jean-Paul
- Angewandte Chemie, Vol. 114, Issue 11
A Boat-Shaped Tetracationic Macrocycle with a Semiconducting Organic Framework
journal, April 2017
- Nguyen, Minh T.; Krzyaniak, Matthew D.; Owczarek, Magdalena
- Angewandte Chemie International Edition, Vol. 56, Issue 21
Self-Assembling Organic Nanotubes
journal, March 2001
- Bong, Dennis T.; Clark, Thomas D.; Granja, Juan R.
- Angewandte Chemie International Edition, Vol. 40, Issue 6
Self-Organized Heteroditopic Macrocyclic Superstructures
journal, August 2003
- Barboiu, Mihail; Vaughan, Gavin; van der Lee, Arie
- Organic Letters, Vol. 5, Issue 17
Mechanisch verzahnte Moleküle (MIMs) - molekulare Shuttle, Schalter und Maschinen (Nobel-Aufsatz)
journal, August 2017
- Stoddart, J. Fraser
- Angewandte Chemie, Vol. 129, Issue 37
Kohlenhydrat-Nanoröhren
journal, July 1997
- Gattuso, Giuseppe; Menzer, Stephan; Nepogodiev, Sergey A.
- Angewandte Chemie, Vol. 109, Issue 13-14
Catenanes: Fifty Years of Molecular Links
journal, May 2015
- Gil-Ramírez, Guzmán; Leigh, David A.; Stephens, Alexander J.
- Angewandte Chemie International Edition, Vol. 54, Issue 21
Self-Assembling Organic Nanotubes from Enantiopure Cyclo-N,N′-Linked Oligoureas: Design, Synthesis, and Crystal Structure
journal, June 2002
- Semetey, Vincent; Didierjean, Claude; Briand, Jean-Paul
- Angewandte Chemie International Edition, Vol. 41, Issue 11
Achiral Cyclodextrin Analogues
journal, August 1997
- Ashton, Peter R.; Cantrill, Stuart J.; Gattuso, Giuseppe
- Chemistry - A European Journal, Vol. 3, Issue 8
Molecular Mosaics Formed by a Square Cyclophane and Its Inclusion Complex with Ferrocene
journal, September 1995
- Ashton, Peter R.; Claessens, Christian G.; Hayes, Wayne
- Angewandte Chemie International Edition in English, Vol. 34, Issue 17
Mechanical Bond Formation by Radical Templation
journal, September 2010
- Li, Hao; Fahrenbach, Albert C.; Dey, Sanjeev K.
- Angewandte Chemie, Vol. 122, Issue 44
Self-Assembly of Structures with Addressable Complexity
journal, February 2016
- Jacobs, William M.; Frenkel, Daan
- Journal of the American Chemical Society, Vol. 138, Issue 8
Radically enhanced molecular recognition
journal, December 2009
- Trabolsi, Ali; Khashab, Niveen; Fahrenbach, Albert C.
- Nature Chemistry, Vol. 2, Issue 1
Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes
journal, January 2017
- Liu, Zhichang; Nalluri, Siva Krishna Mohan; Stoddart, J. Fraser
- Chemical Society Reviews, Vol. 46, Issue 9
Toward Self-Organization and Complex Matter
journal, March 2002
- Lehn, J. -M.
- Science, Vol. 295, Issue 5564
Cyclobis(paraquat-p-phenylen), ein tetrakationischer Mehrzweckrezeptor
journal, November 1988
- Odell, Barbara; Reddington, Mark V.; Slawin, Alexandra M. Z.
- Angewandte Chemie, Vol. 100, Issue 11
Cyclophanes within Cyclophanes: The Synthesis of a Pyromellitic Diimide-Based Macrocycle as a Structural Unit in a Molecular Tube and Its Inclusion Phenomena
journal, May 2006
- Iwanaga, Tetsuo; Nakamoto, Ryoma; Yasutake, Mikio
- Angewandte Chemie International Edition, Vol. 45, Issue 22
Pairing-up viologen cations and dications: a microscopic investigation of van der Waals interactions
journal, January 2018
- Gourlaouen, Christophe; Vela, Sergi; Choua, Sylvie
- Physical Chemistry Chemical Physics, Vol. 20, Issue 44
Supramolecular chemistry: from molecular information towards self-organization and complex matter
journal, February 2004
- Lehn, Jean-Marie
- Reports on Progress in Physics, Vol. 67, Issue 3
Toward complex matter: Supramolecular chemistry and self-organization
journal, April 2002
- Lehn, J. -M.
- Proceedings of the National Academy of Sciences, Vol. 99, Issue 8
Cyclobis(paraquat-p-phenylene). A Tetracationic Multipurpose Receptor
journal, November 1988
- Odell, Barbara; Reddington, Mark V.; Slawin, Alexandra M. Z.
- Angewandte Chemie International Edition in English, Vol. 27, Issue 11, p. 1547-1550
Columnar Self-Assembled Ureido Crown Ethers: An Example of Ion-Channel Organization in Lipid Bilayers
journal, July 2006
- Cazacu, Adinela; Tong, Christine; van der Lee, Arie
- Journal of the American Chemical Society, Vol. 128, Issue 29
The self assembly of controllable [2]catenanes
journal, January 1994
- Ashton, Peter R.; Ballardini, Roberto; Balzani, Vincenzo
- J. Chem. Soc., Chem. Commun., Issue 2
Supramolekulare Synthone für das Kristall-Engineering - eine neue organische Synthese
journal, November 1995
- Desiraju, Gautam R.
- Angewandte Chemie, Vol. 107, Issue 21
Mechanically Interlocked Molecules (MIMs)-Molecular Shuttles, Switches, and Machines (Nobel Lecture)
journal, August 2017
- Stoddart, J. Fraser
- Angewandte Chemie International Edition, Vol. 56, Issue 37
Asararenes-A Family of Large Aromatic Macrocycles
journal, February 2013
- Schneebeli, Severin T.; Cheng, Chuyang; Hartlieb, Karel J.
- Chemistry - A European Journal, Vol. 19, Issue 12
para -Bridged Symmetrical Pillar[5]arenes: Their Lewis Acid Catalyzed Synthesis and Host–Guest Property
journal, April 2008
- Ogoshi, Tomoki; Kanai, Suguru; Fujinami, Shuhei
- Journal of the American Chemical Society, Vol. 130, Issue 15
Pillar[5]arenes: fascinating cyclophanes with a bright future
journal, January 2012
- Cragg, Peter J.; Sharma, Kushal
- Chem. Soc. Rev., Vol. 41, Issue 2
Mechanical Bond Formation by Radical Templation
journal, September 2010
- Li, Hao; Fahrenbach, Albert C.; Dey, Sanjeev K.
- Angewandte Chemie International Edition, Vol. 49, Issue 44, p. 8260-8265
Supramolecular Ex plorations: Ex hibiting the Ex tent of Ex tended Cationic Cyclophanes
journal, January 2016
- Dale, Edward J.; Vermeulen, Nicolaas A.; Juríček, Michal
- Accounts of Chemical Research, Vol. 49, Issue 2
Cyclic polyethers and their complexes with metal salts
journal, December 1967
- Pedersen, Charles J.
- Journal of the American Chemical Society, Vol. 89, Issue 26