A contorted nanographene shelter
Abstract
Nanographenes have kindled considerable interest in the fields of materials science and supramolecular chemistry as a result of their unique self-assembling and optoelectronic properties. Encapsulating the contorted nanographenes inside artificial receptors, however, remains challenging. Herein, we report the design and synthesis of a trigonal prismatic hexacationic cage, which has a large cavity and adopts a relatively flexible conformation. It serves as a receptor, not only for planar coronene, but also for contorted nanographene derivatives with diameters of approximately 15 Å and thicknesses of 7 Å. A comprehensive investigation of the host-guest interactions in the solid, solution and gaseous states by experimentation and theoretical calculations reveals collectively an induced-fit binding mechanism with high binding affinities between the cage and the nanographenes. Notably, the photostability of the nanographenes is improved significantly by the ultrafast deactivation of their excited states within the cage. Encapsulating the contorted nanographenes inside the cage provides a noncovalent strategy for regulating their photoreactivity.
- Authors:
-
[1];
[1];
[1];
[1];
[1];
[1];
[1];
[3];
[1];
[5];
[6]
- Northwestern Univ., Evanston, IL (United States)
- Nankai Univ., Tianjin (China)
- Univ. of Pennsylvania, Philadelphia, PA (United States)
- Shaanxi Univ., Xi an (China)
- Nankai Univ., Tianjin (China); Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China)
- Northwestern Univ., Evanston, IL (United States); Univ. of New South Wales, Sydney, NSW (Australia); Zhejiang Univ., Hangzhou (China); ZJU-Hangzhou Global Scientific and Technological Innovation Center, Hangzhou (China)
- Publication Date:
- Research Org.:
- Northwestern Univ., Evanston, IL (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); National Science Foundation (NSF); Northwestern University; Defense Threat Reduction Agency (DTRA)
- OSTI Identifier:
- 1853771
- Grant/Contract Number:
- SC0021314; ECCS-2025633; CHE-1925708; HDTRA1-19-1-0010
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Nature Communications
- Additional Journal Information:
- Journal Volume: 12; Journal Issue: 1; Journal ID: ISSN 2041-1723
- Publisher:
- Nature Publishing Group
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; 77 NANOSCIENCE AND NANOTECHNOLOGY; interlocked molecules; self-assembly; supramolecular chemistry
Citation Formats
Wu, Huang, Wang, Yu, Song, Bo, Wang, Hui-Juan, Zhou, Jiawang, Sun, Yixun, Jones, Leighton O., Liu, Wenqi, Zhang, Long, Zhang, Xuan, Cai, Kang, Chen, Xiao-Yang, Stern, Charlotte L., Wei, Junfa, Farha, Omar K., Anna, Jessica M., Schatz, George C., Liu, Yu, and Fraser Stoddart, J. A contorted nanographene shelter. United States: N. p., 2021.
Web. doi:10.1038/s41467-021-25255-6.
Wu, Huang, Wang, Yu, Song, Bo, Wang, Hui-Juan, Zhou, Jiawang, Sun, Yixun, Jones, Leighton O., Liu, Wenqi, Zhang, Long, Zhang, Xuan, Cai, Kang, Chen, Xiao-Yang, Stern, Charlotte L., Wei, Junfa, Farha, Omar K., Anna, Jessica M., Schatz, George C., Liu, Yu, & Fraser Stoddart, J. A contorted nanographene shelter. United States. https://doi.org/10.1038/s41467-021-25255-6
Wu, Huang, Wang, Yu, Song, Bo, Wang, Hui-Juan, Zhou, Jiawang, Sun, Yixun, Jones, Leighton O., Liu, Wenqi, Zhang, Long, Zhang, Xuan, Cai, Kang, Chen, Xiao-Yang, Stern, Charlotte L., Wei, Junfa, Farha, Omar K., Anna, Jessica M., Schatz, George C., Liu, Yu, and Fraser Stoddart, J. Tue .
"A contorted nanographene shelter". United States. https://doi.org/10.1038/s41467-021-25255-6. https://www.osti.gov/servlets/purl/1853771.
@article{osti_1853771,
title = {A contorted nanographene shelter},
author = {Wu, Huang and Wang, Yu and Song, Bo and Wang, Hui-Juan and Zhou, Jiawang and Sun, Yixun and Jones, Leighton O. and Liu, Wenqi and Zhang, Long and Zhang, Xuan and Cai, Kang and Chen, Xiao-Yang and Stern, Charlotte L. and Wei, Junfa and Farha, Omar K. and Anna, Jessica M. and Schatz, George C. and Liu, Yu and Fraser Stoddart, J.},
abstractNote = {Nanographenes have kindled considerable interest in the fields of materials science and supramolecular chemistry as a result of their unique self-assembling and optoelectronic properties. Encapsulating the contorted nanographenes inside artificial receptors, however, remains challenging. Herein, we report the design and synthesis of a trigonal prismatic hexacationic cage, which has a large cavity and adopts a relatively flexible conformation. It serves as a receptor, not only for planar coronene, but also for contorted nanographene derivatives with diameters of approximately 15 Å and thicknesses of 7 Å. A comprehensive investigation of the host-guest interactions in the solid, solution and gaseous states by experimentation and theoretical calculations reveals collectively an induced-fit binding mechanism with high binding affinities between the cage and the nanographenes. Notably, the photostability of the nanographenes is improved significantly by the ultrafast deactivation of their excited states within the cage. Encapsulating the contorted nanographenes inside the cage provides a noncovalent strategy for regulating their photoreactivity.},
doi = {10.1038/s41467-021-25255-6},
journal = {Nature Communications},
number = 1,
volume = 12,
place = {United States},
year = {Tue Aug 31 00:00:00 EDT 2021},
month = {Tue Aug 31 00:00:00 EDT 2021}
}
Free Publicly Available Full Text
Publisher's Version of Record
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 Polymeric Materials via Cyclodextrin–Guest Interactions
journal, April 2014
- Harada, Akira; Takashima, Yoshinori; Nakahata, Masaki
- Accounts of Chemical Research, Vol. 47, Issue 7
Concyclic CH-π arrays for single-axis rotations of a bowl in a tube
journal, September 2018
- Matsuno, Taisuke; Fujita, Masahiro; Fukunaga, Kengo
- Nature Communications, Vol. 9, Issue 1
New advances in nanographene chemistry
journal, January 2015
- Narita, Akimitsu; Wang, Xiao-Ye; Feng, Xinliang
- Chemical Society Reviews, Vol. 44, Issue 18
Photochemical Stability of Pentacene and a Substituted Pentacene in Solution and in Thin Films
journal, November 2004
- Maliakal, Ashok; Raghavachari, Krishnan; Katz, Howard
- Chemistry of Materials, Vol. 16, Issue 24
Design Principles for the Optimization of Guest Binding in Aromatic-Paneled Fe II 4 L 6 Cages
journal, July 2017
- Ronson, Tanya K.; Meng, Wenjing; Nitschke, Jonathan R.
- Journal of the American Chemical Society, Vol. 139, Issue 28
Selective Separation of Polyaromatic Hydrocarbons by Phase Transfer of Coordination Cages
journal, November 2019
- Zhang, Dawei; Ronson, Tanya K.; Lavendomme, Roy
- Journal of the American Chemical Society, Vol. 141, Issue 48
Porous organic cages: soluble, modular and molecular pores
journal, July 2016
- Hasell, Tom; Cooper, Andrew I.
- Nature Reviews Materials, Vol. 1, Issue 9
Anion Binding in Solution: Beyond the Electrostatic Regime
journal, September 2017
- Liu, Yun; Sengupta, Arkajyoti; Raghavachari, Krishnan
- Chem, Vol. 3, Issue 3
Interlocked Macromolecules
journal, July 1999
- Raymo, Françisco M.; Stoddart, J. Fraser
- Chemical Reviews, Vol. 99, Issue 7
Controllable Self-Assembly of Macrocycles in Water for Isolating Aromatic Hydrocarbon Isomers
journal, April 2018
- Wu, Guangcheng; Wang, Cai-Yun; Jiao, Tianyu
- Journal of the American Chemical Society, Vol. 140, Issue 18
A Rigid Trigonal-Prismatic Hexagold Metallocage That Behaves as a Coronene Trap
journal, April 2019
- Ibáñez, Susana; Peris, Eduardo
- Angewandte Chemie International Edition, Vol. 58, Issue 20
Calix[4]pyrroles: versatile molecular containers with ion transport, recognition, and molecular switching functions
journal, January 2015
- Kim, Dong Sub; Sessler, Jonathan L.
- Chemical Society Reviews, Vol. 44, Issue 2
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
Using Self-Organization To Control Morphology in Molecular Photovoltaics
journal, January 2013
- Kang, Seok Ju; Ahn, Seokhoon; Kim, Jong Bok
- Journal of the American Chemical Society, Vol. 135, Issue 6
The Design of Molecular Hosts, Guests, and Their Complexes (Nobel Lecture)
journal, August 1988
- Cram, Donald J.
- Angewandte Chemie International Edition in English, Vol. 27, Issue 8
Isostructural, Alternately-Charged Receptor Stacks. The Inclusion Complexes of Hydroquinone and Catechol Dimethyl Ethers with Cyclobis(paraquat-p-phenylene)
journal, November 1988
- Ashton, Peter R.; Odell, Barbara; Reddington, Mark V.
- Angewandte Chemie International Edition in English, Vol. 27, Issue 11
The Discovery of Crown Ethers (Noble Lecture)
journal, August 1988
- Pedersen, Charles J.
- Angewandte Chemie International Edition in English, Vol. 27, Issue 8
Barely porous organic cages for hydrogen isotope separation
journal, October 2019
- Liu, Ming; Zhang, Linda; Little, Marc A.
- Science, Vol. 366, Issue 6465
Aromatic Molecular-Bowl Hydrocarbons: Synthetic Derivatives, Their Structures, and Physical Properties
journal, December 2006
- Wu, Yao-Ting; Siegel, Jay S.
- Chemical Reviews, Vol. 106, Issue 12
Dimensional Matching versus Induced‐Fit Distortions: Binding Affinities of Planar and Curved Polyaromatic Hydrocarbons with a Tetragold Metallorectangle
journal, March 2020
- Ibáñez, Susana; Peris, Eduardo
- Angewandte Chemie International Edition, Vol. 59, Issue 17
Host–Guest Recognition and Fluorescence of a Tetraphenylethene‐Based Octacationic Cage
journal, January 2020
- Duan, Honghong; Li, Yawen; Li, Qingfang
- Angewandte Chemie International Edition, Vol. 59, Issue 25
The Key–Lock Theory and the Induced Fit Theory
journal, January 1995
- Koshland, Daniel E.
- Angewandte Chemie International Edition in English, Vol. 33, Issue 2324
Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry
journal, January 2010
- Hua, Yuran; Flood, Amar H.
- Chemical Society Reviews, Vol. 39, Issue 4
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
Diodelike Current–Voltage Curves for a Single Molecule–Tunneling Spectroscopy with Submolecular Resolution of an Alkylated,peri-Condensed Hexabenzocoronene
journal, August 1995
- Stabel, Andreas; Herwig, Peter; Müllen, Klaus
- Angewandte Chemie International Edition in English, Vol. 34, Issue 15
Guest encapsulation and coronene–C60 exchange in supramolecular zinc porphyrin tweezers, grids and prisms
journal, January 2013
- Samanta, Soumen K.; Schmittel, Michael
- Organic & Biomolecular Chemistry, Vol. 11, Issue 19
Ring-in-Ring(s) Complexes Exhibiting Tunable Multicolor Photoluminescence
journal, September 2020
- Wu, Huang; Wang, Yu; Jones, Leighton O.
- Journal of the American Chemical Society, Vol. 142, Issue 39
Graphenes as Potential Material for Electronics
journal, March 2007
- Wu, Jishan; Pisula, Wojciech; Müllen, Klaus
- Chemical Reviews, Vol. 107, Issue 3
Induced-fit catalysis of corannulene bowl-to-bowl inversion
journal, January 2014
- Juríček, Michal; Strutt, Nathan L.; Barnes, Jonathan C.
- Nature Chemistry, Vol. 6, Issue 3
Functionalized cucurbiturils and their applications
journal, January 2007
- Kim, Kimoon; Selvapalam, Narayanan; Ko, Young Ho
- Chemical Society Reviews, Vol. 36, Issue 2, p. 267-279
Nanographenes as Active Components of Single-Molecule Electronics and How a Scanning Tunneling Microscope Puts Them To Work
journal, April 2008
- Müllen, Klaus; Rabe, Jürgen P.
- Accounts of Chemical Research, Vol. 41, Issue 4
Calixpyrroles II
journal, November 2001
- Gale, Philip A.; Anzenbacher Jr., Pavel; Sessler, Jonathan L.
- Coordination Chemistry Reviews, Vol. 222, Issue 1
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
Synthesis, Structure, Photophysical Properties, and Photostability of Benzodipyrenes
journal, December 2018
- Yang, Wenlong; Monteiro, Jorge H. S. K.; de Bettencourt‐Dias, Ana
- Chemistry – A European Journal, Vol. 25, Issue 6
ExCage
journal, July 2014
- Dale, Edward J.; Vermeulen, Nicolaas A.; Thomas, Andy A.
- Journal of the American Chemical Society, Vol. 136, Issue 30
Novel Cavity Design Using Calix[ n ]arene Skeletons: Toward Molecular Recognition and Metal Binding
journal, August 1997
- Ikeda, Atsushi; Shinkai, Seiji
- Chemical Reviews, Vol. 97, Issue 5
A Macrocycle Based on a Heptagon‐Containing Hexa‐ peri ‐hexabenzocoronene
journal, June 2020
- Jiménez, Vicente G.; David, Arthur H. G.; Cuerva, Juan M.
- Angewandte Chemie International Edition, Vol. 59, Issue 35
Photoconductive Curved-Nanographene/Fullerene Supramolecular Heterojunctions
journal, April 2019
- Huang, Qiang; Zhuang, Guilin; Jia, Hongxing
- Angewandte Chemie International Edition, Vol. 58, Issue 19
A rational strategy for the realization of chain-growth supramolecular polymerization
journal, February 2015
- Kang, Jiheong; Miyajima, Daigo; Mori, Tadashi
- Science, Vol. 347, Issue 6222
The synthesis, crystal structure and charge-transport properties of hexacene
journal, June 2012
- Watanabe, Motonori; Chang, Yuan Jay; Liu, Shun-Wei
- Nature Chemistry, Vol. 4, Issue 7
Porous organic cages as synthetic water channels
journal, October 2020
- Yuan, Yi Di; Dong, Jinqiao; Liu, Jie
- Nature Communications, Vol. 11, Issue 1
Semiconducting Single Crystals Comprising Segregated Arrays of Complexes of C 60
journal, February 2015
- Barnes, Jonathan C.; Dale, Edward J.; Prokofjevs, Aleksandrs
- Journal of the American Chemical Society, Vol. 137, Issue 6
Synthesis of partially and fully fused polyaromatics by annulative chlorophenylene dimerization
journal, January 2018
- Koga, Yoshito; Kaneda, Takeshi; Saito, Yutaro
- Science, Vol. 359, Issue 6374
Two-photon excited deep-red and near-infrared emissive organic co-crystals
journal, September 2020
- Wang, Yu; Wu, Huang; Li, Penghao
- Nature Communications, Vol. 11, Issue 1
Dearomatization Approach Toward a Superbenzoquinone‐Based Diradicaloid, Tetraradicaloid, and Hexaradicaloid
journal, August 2019
- Li, Guangwu; Han, Yi; Zou, Ya
- Angewandte Chemie International Edition, Vol. 58, Issue 40
Global Aromaticity in Macrocyclic Polyradicaloids: Hückel’s Rule or Baird’s Rule?
journal, July 2019
- Liu, Chunchen; Ni, Yong; Lu, Xuefeng
- Accounts of Chemical Research, Vol. 52, Issue 8
A Zone-Casting Technique for Device Fabrication of Field-Effect Transistors Based on Discotic Hexa-peri-hexabenzocoronene
journal, January 2005
- Pisula, W.; Menon, A.; Stepputat, M.
- Advanced Materials, Vol. 17, Issue 6, p. 684-689
One-shot K-region-selective annulative π-extension for nanographene synthesis and functionalization
journal, February 2015
- Ozaki, Kyohei; Kawasumi, Katsuaki; Shibata, Mari
- Nature Communications, Vol. 6, Issue 1
Photoconductive Coaxial Nanotubes of Molecularly Connected Electron Donor and Acceptor Layers
journal, December 2006
- Yamamoto, Y.; Fukushima, T.; Suna, Y.
- Science, Vol. 314, Issue 5806
Semiconducting Self‐Assembled Nanofibers Prepared from Photostable Octafluorinated Bisanthene Derivatives
journal, April 2017
- Hayashi, Hironobu; Aratani, Naoki; Yamada, Hiroko
- Chemistry – A European Journal, Vol. 23, Issue 29
Rapid Macrocycle Threading by a Fluorescent Dye–Polymer Conjugate in Water with Nanomolar Affinity
journal, June 2015
- Peck, Evan M.; Liu, Wenqi; Spence, Graeme T.
- Journal of the American Chemical Society, Vol. 137, Issue 27
The synthesis of 1:2, 3:4, 5:6, 7:8, 9:10, 11:12-hexabenzocoronene
journal, January 1965
- Clar, E.; Stephen, J. F.
- Tetrahedron, Vol. 21, Issue 2
Two‐Photon Absorption Enhancement by the Inclusion of a Tropone Ring in Distorted Nanographene Ribbons
journal, April 2020
- Castro‐Fernández, Silvia; Cruz, Carlos M.; Mariz, Inês F. A.
- Angewandte Chemie International Edition, Vol. 59, Issue 18
Functional Supramolecular Polymeric Networks: The Marriage of Covalent Polymers and Macrocycle-Based Host–Guest Interactions
journal, May 2020
- Xia, Danyu; Wang, Pi; Ji, Xiaofan
- Chemical Reviews, Vol. 120, Issue 13
Effect of Molecular Packing on Corannulene-Based Materials Electroluminescence
journal, August 2011
- Zoppi, Laura; Martin-Samos, Layla; Baldridge, Kim K.
- Journal of the American Chemical Society, Vol. 133, Issue 35
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
Controlled Doping in Thin-Film Transistors of Large Contorted Aromatic Compounds
journal, March 2013
- Xiao, Shengxiong; Kang, Seok Ju; Zhong, Yu
- Angewandte Chemie International Edition, Vol. 52, Issue 17
Facile Bottom-Up Synthesis of Coronene-based 3-Fold Symmetrical and Highly Substituted Nanographenes from Simple Aromatics
journal, February 2014
- Zhang, Qiang; Peng, Hanqing; Zhang, Guishan
- Journal of the American Chemical Society, Vol. 136, Issue 13
Polyaromatic molecular peanuts
journal, June 2017
- Yazaki, Kohei; Akita, Munetaka; Prusty, Soumyakanta
- Nature Communications, Vol. 8, Issue 1
A flexible self-folding receptor for coronene
journal, January 2019
- Lozano, David; Álvarez-Yebra, Rubén; López-Coll, Ricard
- Chemical Science, Vol. 10, Issue 44
Self-Assembled Hexa-peri-hexabenzocoronene Graphitic Nanotube
journal, June 2004
- Hill, J. P.
- Science, Vol. 304, Issue 5676
The chemistry of the mechanical bond
journal, January 2009
- Stoddart, J. Fraser
- Chemical Society Reviews, Vol. 38, Issue 6, p. 1802-1820
Positive and negative regulation of carbon nanotube catalysts through encapsulation within macrocycles
journal, July 2018
- Blanco, Matías; Nieto-Ortega, Belén; de Juan, Alberto
- Nature Communications, Vol. 9, Issue 1
Coaxially Stacked Coronene Columns inside Single-Walled Carbon Nanotubes
journal, March 2011
- Okazaki, Toshiya; Iizumi, Yoko; Okubo, Shingo
- Angewandte Chemie International Edition, Vol. 50, Issue 21
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
Compressed Corannulene in a Molecular Cage
journal, December 2015
- Schmidt, Bernd M.; Osuga, Takafumi; Sawada, Tomohisa
- Angewandte Chemie International Edition, Vol. 55, Issue 4
A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes
journal, June 2013
- Lee, Semin; Chen, Chun-Hsing; Flood, Amar H.
- Nature Chemistry, Vol. 5, Issue 8
Molecular-Scale Porous Materials Based on Pillar[n]arenes
journal, September 2018
- Song, Nan; Kakuta, Takahiro; Yamagishi, Tada-aki
- Chem, Vol. 4, Issue 9