Simultaneous Self-Assembly of a [2]Catenane, a Trefoil Knot, and a Solomon Link from a Simple Pair of Ligands†
Dr. Thirumurugan Prakasam
Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)
Search for more papers by this authorDr. Matteo Lusi
Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)
Search for more papers by this authorDr. Mourad Elhabiri
Laboratoire de Chimie Bioorganique et Médicinale, UMR 7509 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Search for more papers by this authorDr. Carlos Platas-Iglesias
Departamento de Química Fundamental, Universidade da Coruña, Campus da Zapateira, Rúa da Fraga 10, 15008 A Coruña (Spain)
Search for more papers by this authorProf. John-Carl Olsen
School of Sciences, Indiana University Kokomo, Kokomo, IN 46904 (USA)
Search for more papers by this authorDr. Zouhair Asfari
Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Search for more papers by this authorDr. Sarah Cianférani-Sanglier
Laboratoire de Spectrométrie de Masse Bio-Organique, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Search for more papers by this authorDr. François Debaene
Laboratoire de Spectrométrie de Masse Bio-Organique, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Search for more papers by this authorCorresponding Author
Dr. Loïc J. Charbonnière
Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Loïc J. Charbonnière, Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)===
Ali Trabolsi, Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)===
Search for more papers by this authorCorresponding Author
Prof. Ali Trabolsi
Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)
Loïc J. Charbonnière, Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)===
Ali Trabolsi, Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)===
Search for more papers by this authorDr. Thirumurugan Prakasam
Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)
Search for more papers by this authorDr. Matteo Lusi
Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)
Search for more papers by this authorDr. Mourad Elhabiri
Laboratoire de Chimie Bioorganique et Médicinale, UMR 7509 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Search for more papers by this authorDr. Carlos Platas-Iglesias
Departamento de Química Fundamental, Universidade da Coruña, Campus da Zapateira, Rúa da Fraga 10, 15008 A Coruña (Spain)
Search for more papers by this authorProf. John-Carl Olsen
School of Sciences, Indiana University Kokomo, Kokomo, IN 46904 (USA)
Search for more papers by this authorDr. Zouhair Asfari
Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Search for more papers by this authorDr. Sarah Cianférani-Sanglier
Laboratoire de Spectrométrie de Masse Bio-Organique, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Search for more papers by this authorDr. François Debaene
Laboratoire de Spectrométrie de Masse Bio-Organique, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Search for more papers by this authorCorresponding Author
Dr. Loïc J. Charbonnière
Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)
Loïc J. Charbonnière, Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)===
Ali Trabolsi, Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)===
Search for more papers by this authorCorresponding Author
Prof. Ali Trabolsi
Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)
Loïc J. Charbonnière, Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, IPHC, UMR 7178 CNRS-Université de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg (France)===
Ali Trabolsi, Centre for Science and Engineering, New York University, Abu Dhabi (NYUAD) (United Aarab Emirates, UAE)===
Search for more papers by this authorThe research described herein was sponsored by the New York University Abu Dhabi (NYUAD), in the UAE. T.P., M.L., and A.T. thank the NYUAD for generous support. M.E., S.C.S., F.D., Z.A., and L.C. thank the Centre National de la Recherche Scientifique (CNRS), the University of Strasbourg, and the Region Alsace in France for financial support. C.P.I. thanks Centro de Supercomputación de Galicia (CESGA) for providing the computer facilities. We thank A.C. Fahrenbach for useful discussions and B. Curzadd for the 3D cartoons.
Graphical Abstract
A topological triptych: Three molecular links, a [2]catenane, a trefoil knot, and a Solomon link, were obtained in one pot through the self-assembly of two simple ligands in the presence of ZnII (see picture). The approach relied on dynamic covalent chemistry and metal templation.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| anie_201302425_sm_miscellaneous_information.pdf9.8 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
- 1R. S. Forgan, J.-P. Sauvage, J. F. Stoddart, Chem. Rev. 2011, 111, 5434–5464.
- 2“Templates in Chemistry II”: C. Dietrich-Buchecker, B. Colasson, J.-P. Sauvage, Topics in Current Chemistry, Vol. 249, Springer, Berlin, 2005, pp. 261–283.
- 3J.-F. Ayme, J. E. Beves, C. J. Campbell, D. A. Leigh, Chem. Soc. Rev. 2013, 42, 1700–1712.
- 4E. E. Fenlon, Eur. J. Org. Chem. 2008, 5023–5035.
- 5O. Lukin, F. Vögtle, Angew. Chem. 2005, 117, 1480–1501;
10.1002/ange.200460312 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 1456–1477.
- 6J.-M. Lehn, Chem. Soc. Rev. 2007, 36, 151–160.
- 7C. Dietrich-Buchecker, G. Rapenne, J.-P. Sauvage, Molecular Catenanes, Rotaxanes and Knots, Wiley-VCH, Weinheim, 2007, pp. 107–142.
- 8J. F. Stoddart, Chem. Soc. Rev. 2009, 38, 1802–1820.
- 9
- 9aN. Ponnuswamy, F. B. L. Cougnon, J. M. Clough, G. D. Pantoş, J. K. M. Sanders, Science 2012, 338, 783–785;
- 9bF. Davis, S. Higson, Macrocycles: Construction, Chemistry and Nanotechnology Applications, Wiley, Chichester, 2011, pp. 381–517.
10.1002/9780470980200.ch9 Google Scholar
- 10J. D. Crowley, S. M. Goldup, A.-L. Lee, D. A. Leigh, R. T. McBurney, Chem. Soc. Rev. 2009, 38, 1530–1541.
- 11C. O. Dietrich-Buchecker, J.-P. Sauvage, J. M. Kern, J. Am. Chem. Soc. 1984, 106, 3043–3045.
- 12S. Durot, F. Reviriego, J.-P. Sauvage, Dalton Trans. 2010, 39, 10557–10570.
- 13F. M. Raymo, J. F. Stoddart, Molecular Catenanes, Rotaxanes and Knots, Wiley-VCH, Weinheim, 2007, pp. 143–176.
- 14
- 14aH. Y. Au-Yeung, F. B. L. Cougnon, S. Otto, D. Pantos, J. K. M. Sanders, Chem. Sci. 2010, 1, 567–574;
- 14bF. B. L. Cougnon, J. K. M. Sanders, Acc. Chem. Res. 2012, 45, 2211–2221.
- 15
- 15aL. F. Liu, L. Perkocha, R. Calendar, J. C. Wang, Proc. Natl. Acad. Sci. USA 1981, 78, 5498–5502;
- 15bL. F. Liu, R. E. Depew, J. C. Wang, J. Mol. Biol. 1976, 106, 439–452;
- 15cS. Kamitori, J. Am. Chem. Soc. 1996, 118, 8945–8946;
- 15dC. Liang, K. Mislow, J. Am. Chem. Soc. 1994, 116, 11189–11190;
- 15eW. R. Taylor, Nature 2000, 406, 916–919.
- 16C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1989, 101, 192–194; Angew. Chem. Int. Ed. Engl. 1989, 28, 189–192.
- 17
- 17aL.-E. Perret-Aebi, A. von Zelewsky, C. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 2004, 116, 4582–4585;
10.1002/ange.200460250 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 4482–4485;
- 17bP. R. Ashton, O. A. Matthews, S. Menzer, F. M. Raymo, N. Spencer, J. F. Stoddart, D. J. Williams, Liebigs Ann. 1997, 2485–2494;
- 17cP. E. Barran, H. L. Cole, S. M. Goldup, D. A. Leigh, P. R. McGonigal, M. D. Symes, J. Wu, M. Zengerle, Angew. Chem. 2011, 123, 12488–12492;
10.1002/ange.201105012 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 12280–12284;
- 17dC. O. Dietrich-Buchecker, J. Guilhem, C. Pascard, J.-P. Sauvage, Angew. Chem. 1990, 102, 1202–1204; Angew. Chem. Int. Ed. Engl. 1990, 29, 1154–1156;
- 17eC. O. Dietrich-Buchecker, J.-P. Sauvage, A. De Cian, J. Fischer, J. Chem. Soc. Chem. Commun. 1994, 2231–2232;
- 17fC. O. Ditrich-Buchecker, J. F. Nierengarten, J. P. Sauvage, Tetrahedron Lett. 1992, 33, 3625–3628.
10.1016/S0040-4039(00)92519-X Google Scholar
- 18
- 18aJ. F. Nierengarten, C. O. Dietrich-Buchecker, J. P. Sauvage, J. Am. Chem. Soc. 1994, 116, 375–376;
- 18bC. P. McArdle, J. J. Vittal, R. J. Puddephatt, Angew. Chem. 2000, 112, 3977–3980;
10.1002/1521-3757(20001103)112:21<3977::AID-ANGE3977>3.0.CO;2-E Google ScholarAngew. Chem. Int. Ed. 2000, 39, 3819–3822;10.1002/1521-3773(20001103)39:21<3819::AID-ANIE3819>3.0.CO;2-6 CAS PubMed Web of Science® Google Scholar
- 18cC. D. Pentecost, K. S. Chichak, A. J. Peters, G. W. V. Cave, S. J. Cantrill, J. F. Stoddart, Angew. Chem. 2007, 119, 222–226;
10.1002/ange.200603521 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 218–222;
- 18dC. Peinador, V. C. Blanco, J. M. Quintela, J. Am. Chem. Soc. 2009, 131, 920–921;
- 18eC. P. McArdle, M. C. Jennings, J. J. Vittal, R. J. Puddephatt, Chem. Eur. J. 2001, 7, 3572–3583.
10.1002/1521-3765(20010817)7:16<3572::AID-CHEM3572>3.0.CO;2-C CAS PubMed Web of Science® Google Scholar
- 19
- 19aD. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586–1591;
10.1002/1521-3757(20010417)113:8<1586::AID-ANGE1586>3.0.CO;2-3 Google ScholarAngew. Chem. Int. Ed. 2001, 40, 1538–1543;10.1002/1521-3773(20010417)40:8<1538::AID-ANIE1538>3.0.CO;2-F CAS PubMed Web of Science® Google Scholar
- 19bL. Hogg, D. A. Leigh, P. J. Lusby, A. Morelli, S. Parsons, J. K. Y. Wong, Angew. Chem. 2004, 116, 1238–1241;
10.1002/ange.200353186 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 1218–1221;
- 19cM. E. Belowich, J. F. Stoddart, Chem. Soc. Rev. 2012, 41, 2003–2024.
- 20K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart, Science 2004, 304, 1308–1312.
- 21C. D. Meyer, R. S. Forgan, K. S. Chichak, A. J. Peters, N. Tangchaivang, G. W. V. Cave, S. I. Khan, S. J. Cantrill, J. F. Stoddart, Chem. Eur. J. 2010, 16, 12570–12581.
- 22
- 22aS. J. Cantrill, K. S. Chichak, A. J. Peters, J. F. Stoddart, Acc. Chem. Res. 2005, 38, 1–9;
- 22bK. S. Chichak, A. J. Peters, S. J. Cantrill, J. F. Stoddart, J. Org. Chem. 2005, 70, 7956–7962;
- 22cK. S. Chichak, S. J. Cantrill, J. F. Stoddart, Chem. Commun. 2005, 3391–3393.
- 23
- 23aJ.-M. Lehn, Science 2002, 295, 2400–2403;
- 23bD. H. Busch, Coord. Chem. Rev. 1990, 100, 119–154;
- 23cD. A. Leigh, A. Venturini, A. J. Wilson, J. K. Y. Wong, F. Zerbetto, Chem. Eur. J. 2004, 10, 4960–4969.
