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Title: Supramolecular Ex plorations: Ex hibiting the Ex tent of Ex tended Cationic Cyclophanes

Abstract

Acting as hosts, cationic cyclophanes, consisting of π-electron-poor bipyridinium units, are capable of entering into strong donor–acceptor interactions to form host–guest complexes with various guests when the size and electronic constitution are appropriately matched. A synthetic protocol has been developed that utilizes catalytic quantities of tetrabutylammonium iodide to make a wide variety of cationic pyridinium-based cyclophanes in a quick and easy manner. Members of this class of cationic cyclophanes with boxlike geometries, dubbed ExnBoxm4+ for short, have been prepared by altering a number of variables: (i) n, the number of “horizontal” p-phenylene spacers between adjoining pyridinium units, to modulate the “length” of the cavity; (ii) m, the number of “vertical” p-phenylene spacers, to modulate the “width” of the cavity; and (iii) the aromatic linkers, namely, 1,4-di- and 1,3,5-trisubstituted units for the construction of macrocycles (ExBoxes) and macrobicycles (ExCages), respectively. This Account serves as an exploration of the properties that emerge from these structural modifications of the pyridinium-based hosts, coupled with a call for further investigation into the wealth of properties inherent in this class of compounds. By variation of only the aforementioned components, the role of these cationic receptors covers ground that spans (i) synthetic methodology, (ii) extraction and sequestration,more » (iii) catalysis, (iv) molecular electronics, (v) physical organic chemistry, and (vi) supramolecular chemistry. Ex1Box4+ (or simply ExBox4+) has been shown to be a multipurpose receptor capable of binding a wide range of polycyclic aromatic hydrocarbons (PAHs), while also being a suitable component in switchable mechanically interlocked molecules. Additionally, the electronic properties of some host–guest complexes allow the development of artificial photosystems. Ex2Box4+ boasts the ability to bind both π-electron-rich and -poor aromatic guests in different binding sites located within the same cavity. ExBox24+ forms complexes with C60 in which discrete arrays of aligned fullerenes result in single cocrystals, leading to improved material conductivities. When the substitution pattern of the ExnBox4+ series is changed to 1,3,5-trisubstituted benzenoid cores, the hexacationic cagelike compound, termed ExCage6+, exhibits different kinetics of complexation with guests of varying sizes—a veritable playground for physical organic chemists. The organization of functionality with respect to structure becomes valuable as the number of analogues continues to grow. With each of these minor structural modifications, a wealth of properties emerge, begging the question as to what discoveries await and what properties will be realized with the continued exploration of this area of supramolecular chemistry based on a unique class of receptor molecules.« less

Authors:
 [1];  [1];  [2];  [3];  [4];  [4];  [1]
  1. Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
  2. Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
  3. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States
  4. Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States, Argonne−Northwestern Solar Energy Research (ANSER) Center, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
Publication Date:
Research Org.:
Northwestern Univ., Evanston, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division
OSTI Identifier:
1248415
Alternate Identifier(s):
OSTI ID: 1434641
Grant/Contract Number:  
FG02-99ER14999
Resource Type:
Published Article
Journal Name:
Accounts of Chemical Research
Additional Journal Information:
Journal Name: Accounts of Chemical Research Journal Volume: 49 Journal Issue: 2; Journal ID: ISSN 0001-4842
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Dale, Edward J., Vermeulen, Nicolaas A., Juríček, Michal, Barnes, Jonathan C., Young, Ryan M., Wasielewski, Michael R., and Stoddart, J. Fraser. Supramolecular Ex plorations: Ex hibiting the Ex tent of Ex tended Cationic Cyclophanes. United States: N. p., 2016. Web. doi:10.1021/acs.accounts.5b00495.
Dale, Edward J., Vermeulen, Nicolaas A., Juríček, Michal, Barnes, Jonathan C., Young, Ryan M., Wasielewski, Michael R., & Stoddart, J. Fraser. Supramolecular Ex plorations: Ex hibiting the Ex tent of Ex tended Cationic Cyclophanes. United States. doi:10.1021/acs.accounts.5b00495.
Dale, Edward J., Vermeulen, Nicolaas A., Juríček, Michal, Barnes, Jonathan C., Young, Ryan M., Wasielewski, Michael R., and Stoddart, J. Fraser. Tue . "Supramolecular Ex plorations: Ex hibiting the Ex tent of Ex tended Cationic Cyclophanes". United States. doi:10.1021/acs.accounts.5b00495.
@article{osti_1248415,
title = {Supramolecular Ex plorations: Ex hibiting the Ex tent of Ex tended Cationic Cyclophanes},
author = {Dale, Edward J. and Vermeulen, Nicolaas A. and Juríček, Michal and Barnes, Jonathan C. and Young, Ryan M. and Wasielewski, Michael R. and Stoddart, J. Fraser},
abstractNote = {Acting as hosts, cationic cyclophanes, consisting of π-electron-poor bipyridinium units, are capable of entering into strong donor–acceptor interactions to form host–guest complexes with various guests when the size and electronic constitution are appropriately matched. A synthetic protocol has been developed that utilizes catalytic quantities of tetrabutylammonium iodide to make a wide variety of cationic pyridinium-based cyclophanes in a quick and easy manner. Members of this class of cationic cyclophanes with boxlike geometries, dubbed ExnBoxm4+ for short, have been prepared by altering a number of variables: (i) n, the number of “horizontal” p-phenylene spacers between adjoining pyridinium units, to modulate the “length” of the cavity; (ii) m, the number of “vertical” p-phenylene spacers, to modulate the “width” of the cavity; and (iii) the aromatic linkers, namely, 1,4-di- and 1,3,5-trisubstituted units for the construction of macrocycles (ExBoxes) and macrobicycles (ExCages), respectively. This Account serves as an exploration of the properties that emerge from these structural modifications of the pyridinium-based hosts, coupled with a call for further investigation into the wealth of properties inherent in this class of compounds. By variation of only the aforementioned components, the role of these cationic receptors covers ground that spans (i) synthetic methodology, (ii) extraction and sequestration, (iii) catalysis, (iv) molecular electronics, (v) physical organic chemistry, and (vi) supramolecular chemistry. Ex1Box4+ (or simply ExBox4+) has been shown to be a multipurpose receptor capable of binding a wide range of polycyclic aromatic hydrocarbons (PAHs), while also being a suitable component in switchable mechanically interlocked molecules. Additionally, the electronic properties of some host–guest complexes allow the development of artificial photosystems. Ex2Box4+ boasts the ability to bind both π-electron-rich and -poor aromatic guests in different binding sites located within the same cavity. ExBox24+ forms complexes with C60 in which discrete arrays of aligned fullerenes result in single cocrystals, leading to improved material conductivities. When the substitution pattern of the ExnBox4+ series is changed to 1,3,5-trisubstituted benzenoid cores, the hexacationic cagelike compound, termed ExCage6+, exhibits different kinetics of complexation with guests of varying sizes—a veritable playground for physical organic chemists. The organization of functionality with respect to structure becomes valuable as the number of analogues continues to grow. With each of these minor structural modifications, a wealth of properties emerge, begging the question as to what discoveries await and what properties will be realized with the continued exploration of this area of supramolecular chemistry based on a unique class of receptor molecules.},
doi = {10.1021/acs.accounts.5b00495},
journal = {Accounts of Chemical Research},
number = 2,
volume = 49,
place = {United States},
year = {2016},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
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DOI: 10.1021/acs.accounts.5b00495

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Cited by: 32 works
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Works referencing / citing this record:

A Boat-Shaped Tetracationic Macrocycle with a Semiconducting Organic Framework
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  • Li, Bin; Wang, Bin; Huang, Xiayang
  • Angewandte Chemie International Edition, Vol. 58, Issue 12
  • DOI: 10.1002/anie.201813972

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  • Anamimoghadam, Ommid; Cooper, James A.; Nguyen, Minh T.
  • Angewandte Chemie International Edition, Vol. 58, Issue 39
  • DOI: 10.1002/anie.201907329

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  • Ueda, Misa; Horiuchi, Shinnosuke; Sakuda, Eri
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  • Chemical Science, Vol. 10, Issue 15
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  • Gong, Teng; Li, Peng; Sui, Qi
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  • Cheng, Lin; Zhang, Haiyang; Dong, Yunhong
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  • DOI: 10.1039/c9cc00599d

Adjustable chiral self-sorting and self-discriminating behaviour between diamond-like Tröger's base-linked cryptands
journal, January 2019

  • Chen, Yuan; Qian, Cheng; Zhao, Qian
  • Chemical Communications, Vol. 55, Issue 56
  • DOI: 10.1039/c9cc03577j

Unexpected solvent effect on the binding of positively-charged macrocycles to neutral aromatic hydrocarbons
journal, January 2019

  • Wang, Yu-Mei; Yao, Huan; Quan, Mao
  • Chemical Communications, Vol. 55, Issue 73
  • DOI: 10.1039/c9cc06154a

Guest recognition enhanced by lateral interactions
journal, January 2019

  • Jiao, Tianyu; Cai, Kang; Liu, Zhichang
  • Chemical Science, Vol. 10, Issue 19
  • DOI: 10.1039/c9sc00591a

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
  • DOI: 10.1002/ange.201702019

Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes
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  • Liu, Zhichang; Nalluri, Siva Krishna Mohan; Stoddart, J. Fraser
  • Chemical Society Reviews, Vol. 46, Issue 9
  • DOI: 10.1039/c7cs00185a

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  • Nguyen, Minh T.; Krzyaniak, Matthew D.; Owczarek, Magdalena
  • Angewandte Chemie, Vol. 129, Issue 21
  • DOI: 10.1002/ange.201702019

A Switchable Open/closed Polyaromatic Macrocycle that Shows Reversible Binding of Long Hydrophilic Molecules
journal, August 2017

  • Kurihara, Kohei; Yazaki, Kohei; Akita, Munetaka
  • Angewandte Chemie International Edition, Vol. 56, Issue 38
  • DOI: 10.1002/anie.201703357

Construction of π-Surface-Metalated Pillar[5]arenes which Bind Anions via Anion-π Interactions
journal, October 2017

  • Jiang, Bo; Wang, Wei; Zhang, Ying
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  • DOI: 10.1002/anie.201707209

Blurring the Lines between Host and Guest: A Chimeric Receptor Derived from Cucurbituril and Triptycene
journal, May 2018

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  • Angewandte Chemie International Edition, Vol. 57, Issue 27
  • DOI: 10.1002/anie.201803132

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journal, January 2019

  • Li, Bin; Wang, Bin; Huang, Xiayang
  • Angewandte Chemie International Edition, Vol. 58, Issue 12
  • DOI: 10.1002/anie.201813972

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  • Anamimoghadam, Ommid; Cooper, James A.; Nguyen, Minh T.
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  • DOI: 10.1002/chem.201702659

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  • DOI: 10.1002/ejoc.201701124

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journal, January 2017

  • Ueda, Misa; Horiuchi, Shinnosuke; Sakuda, Eri
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  • DOI: 10.1039/c7cc03447d

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
  • DOI: 10.1039/c7cs00185a

Choosing sides: unusual ultrafast charge transfer pathways in an asymmetric electron-accepting cyclophane that binds an electron donor
journal, January 2019

  • Zhou, Jiawang; Wu, Yilei; Roy, Indranil
  • Chemical Science, Vol. 10, Issue 15
  • DOI: 10.1039/c8sc05514a

A stable electron-deficient metal–organic framework for colorimetric and luminescence sensing of phenols and anilines
journal, January 2018

  • Gong, Teng; Li, Peng; Sui, Qi
  • Journal of Materials Chemistry A, Vol. 6, Issue 19
  • DOI: 10.1039/c8ta02794c

Tetraphenylethene-based tetracationic cyclophanes and their selective recognition for amino acids and adenosine derivatives in water
journal, January 2019

  • Cheng, Lin; Zhang, Haiyang; Dong, Yunhong
  • Chemical Communications, Vol. 55, Issue 16
  • DOI: 10.1039/c9cc00599d

Adjustable chiral self-sorting and self-discriminating behaviour between diamond-like Tröger's base-linked cryptands
journal, January 2019

  • Chen, Yuan; Qian, Cheng; Zhao, Qian
  • Chemical Communications, Vol. 55, Issue 56
  • DOI: 10.1039/c9cc03577j

Unexpected solvent effect on the binding of positively-charged macrocycles to neutral aromatic hydrocarbons
journal, January 2019

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  • Chemical Communications, Vol. 55, Issue 73
  • DOI: 10.1039/c9cc06154a

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  • Jiao, Tianyu; Cai, Kang; Liu, Zhichang
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  • DOI: 10.1039/c9sc00591a

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