Large Self-Assembled Chiral Organic Cages: Synthesis, Structure, and Shape Persistence†
Dr. Kim E. Jelfs
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
These authors contributed equally.
Search for more papers by this authorDr. Xiaofeng Wu
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
These authors contributed equally.
Search for more papers by this authorDr. Marc Schmidtmann
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Search for more papers by this authorDr. James T. A. Jones
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Search for more papers by this authorDr. John E. Warren
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Search for more papers by this authorDr. Dave J. Adams
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Search for more papers by this authorCorresponding Author
Prof. Andrew I. Cooper
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)Search for more papers by this authorDr. Kim E. Jelfs
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
These authors contributed equally.
Search for more papers by this authorDr. Xiaofeng Wu
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
These authors contributed equally.
Search for more papers by this authorDr. Marc Schmidtmann
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Search for more papers by this authorDr. James T. A. Jones
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Search for more papers by this authorDr. John E. Warren
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Search for more papers by this authorDr. Dave J. Adams
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Search for more papers by this authorCorresponding Author
Prof. Andrew I. Cooper
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)
Department of Chemistry, Centre for Materials Discovery, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK)Search for more papers by this authorWe thank the Engineering and Research Council (EPSRC; EP/H000925/1) and the Dutch Polymer Institute for financial support. A.I.C. is a Royal Society Wolfson Research Merit Award holder. We thank the STFC for access to Diamond Light Source and the staff at beamline I19. This work made use of the facilities of HECToR through our membership of the UK’s HPC Materials Chemistry Consortium (EPSRC EP/F067496). We thank D. Willock and D. Holden for the molecular force fields, and G. Tribello for helpful discussions.
Graphical Abstract
Nur gefüllt stabil: Zwei große organische Käfige (siehe Beispiel) mit Hohlraumdurchmessern von 1.2 nm wurden durch [8+12]-Iminkondensation erhalten. Die Materialien werden beim Entfernen des Lösungsmittels amorph und zeigen kaum permanente Porosität. Moleküldynamiksimulationen geben Einblicke in den Mechanismus dieser Abläufe, woraus Strategien für die Synthese großer formbeständiger organischer Käfige ableitbar sind.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
Filename | Description |
---|---|
ange_201105104_sm_miscellaneous_information.pdf2.9 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1M. Mastalerz, Angew. Chem. 2010, 122, 5164;
10.1002/ange.201000443 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 5042.
- 2F. Hof, S. L. Craig, C. Nuckolls, J. Rebek, Jr., Angew. Chem. 2002, 114, 1556;
10.1002/1521-3757(20020503)114:9<1556::AID-ANGE1556>3.0.CO;2-C Google ScholarAngew. Chem. Int. Ed. 2002, 41, 1488.10.1002/1521-3773(20020503)41:9<1488::AID-ANIE1488>3.0.CO;2-G CAS PubMed Web of Science® Google Scholar
- 3A. V. Leontiev, D. M. Rudkevich, Chem. Commun. 2004, 1468.
- 4L. J. Barbour, Chem. Commun. 2006, 1163.
- 5T. Tozawa et al., Nat. Mater. 2009, 8, 973.
- 6N. B. McKeown, J. Mater. Chem. 2010, 20, 10588.
- 7J. R. Holst, A. Trewin, A. I. Cooper, Nat. Chem. 2010, 2, 915.
- 8M. Mastalerz, Chem. Commun. 2008, 4756.
- 9M. Mastalerz, M. W. Schneider, I. M. Oppel, O. Presly, Angew. Chem. 2011, 123, 1078; Angew. Chem. Int. Ed. 2011, 50, 1046.
- 10A. Granzhan, T. Riis-Johannessen, R. Scopelliti, K. Severin, Angew. Chem. 2010, 122, 5647;
10.1002/ange.201002748 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 5515.
- 11T. Hasell, X. Wu, J. T. A. Jones, J. Bacsa, A. Steiner, T. Mitra, A. Trewin, D. J. Adams, A. I. Cooper, Nat. Chem. 2010, 2, 750.
- 12J. Chen, S. Korner, S. L. Craig, D. M. Rudkevich, J. Rebek, Jr., Nature 2002, 415, 385.
- 13P. Skowronek, J. Gawronski, Org. Lett. 2008, 10, 4755.
- 14M. J. MacLachlan, Pure Appl. Chem. 2006, 78, 873.
- 15N. E. Borisova, M. D. Reshetova, Y. A. Ustynyuk, Chem. Rev. 2007, 107, 46.
- 16S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938;
10.1002/1521-3757(20020315)114:6<938::AID-ANGE938>3.0.CO;2-K Google ScholarAngew. Chem. Int. Ed. 2002, 41, 898.10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E CAS PubMed Web of Science® Google Scholar
- 17P. R. Ashton, N. S. Isaacs, F. H. Kohnke, G. S. Dalcontres, J. F. Stoddart, Angew. Chem. 1989, 101, 1269; Angew. Chem. Int. Ed. Engl. 1989, 28, 1261.
- 18H. M. El-Kaderi, J. R. Hunt, J. L. Mendoza-Cortes, A. P. Côté, R. E. Taylor, M. O’Keeffe, O. M. Yaghi, Science 2007, 316, 268.
- 19M. L. C. Quan, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2754.
- 20X. Liu, Y. Liu, G. Li, R. Warmuth, Angew. Chem. 2006, 118, 915; Angew. Chem. Int. Ed. 2006, 45, 901.
- 21X. Liu, R. Warmuth, J. Am. Chem. Soc. 2006, 128, 14120.
- 22Y. Liu, X. Liu, R. Warmuth, Chem. Eur. J. 2007, 13, 8953.
- 23D. Xu, R. Warmuth, J. Am. Chem. Soc. 2008, 130, 7520.
- 24
- 24aQ. F. Sun, J. Iwasa, D. Ogawa, Y. Ishido, S. Sato, T. Ozeki, Y. Sei, K. Yamaguchi, M. Fujita, Science 2010, 328, 1144;
- 24bS. R. Seidel, P. J. Stang, Acc. Chem. Res. 2002, 35, 972.
- 25J. T. A. Jones, T. Hasell, X. F. Wu, J. Bacsa, K. E. Jelfs, M. Schmidtmann, S. Y. Chong, D. J. Adams, A. Trewin, F. Schiffmann, F. Cora, B. Slater, A. Steiner, G. M. Day, A. I. Cooper, Nature 2011, 474, 367.
- 26H. Sun, Macromolecules 1995, 28, 701.
- 27J. T. A. Jones, D. Holden, T. Mitra, T. Hasell, D. J. Adams, K. E. Jelfs, A. Trewin, D. J. Willock, G. M. Day, J. Bacsa, A. Steiner, A. I. Cooper, Angew. Chem. 2011, 123, 775; Angew. Chem. Int. Ed. 2011, 50, 749.
- 28W. Smith, C. W. Yong, P. M. Rodger, Mol. Simul. 2002, 28, 385.
- 29S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104.
- 30J. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865.
- 31J. Vandevondele, J. Hutter, J. Chem. Phys. 2007, 127, 114105.
- 32J. Vandevondele, M. Krack, F. Mohamed, M. Parrinello, T. Chassaing, J. Hutter, Comput. Phys. Commun. 2005, 167, 103.
- 33The CP2K development group; http://cp2k.berlios.de/.
- 34A. M. Walker, B. Civalleri, B. Slater, C. Mellot-Draznieks, F. Cora, C. M. Zicovich-Wilson, G. Roman-Perez, J. M. Soler, J. D. Gale, Angew. Chem. 2010, 122, 7663; Angew. Chem. Int. Ed. 2010, 49, 7501.
- 35C. G. Bezzu, M. Helliwell, J. E. Warren, D. R. Allan, N. B. McKeown, Science 2010, 327, 1627.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.