Nitrogen Directs Multiple Radical Additions to the 9,9′-Bi-1-aza(C60-Ih)[5,6]fullerene: X-ray Structure of 6,9,12,15,18-C59N(CF3)5†
Dr. Natalia B. Shustova
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorDr. Igor V. Kuvychko
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorCorresponding Author
Dr. Alexey A. Popov
Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Alexey A. Popov, Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Andreas Hirsch, Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Steven H. Strauss, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Olga V. Boltalina, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorMax von Delius
Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Search for more papers by this authorProf. Lothar Dunsch
Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Search for more papers by this authorProf. Oren P. Anderson
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorCorresponding Author
Prof. Dr. Andreas Hirsch
Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Alexey A. Popov, Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Andreas Hirsch, Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Steven H. Strauss, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Olga V. Boltalina, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorCorresponding Author
Prof. Steven H. Strauss
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Alexey A. Popov, Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Andreas Hirsch, Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Steven H. Strauss, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Olga V. Boltalina, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorCorresponding Author
Dr. Olga V. Boltalina
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Alexey A. Popov, Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Andreas Hirsch, Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Steven H. Strauss, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Olga V. Boltalina, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorDr. Natalia B. Shustova
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorDr. Igor V. Kuvychko
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorCorresponding Author
Dr. Alexey A. Popov
Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Alexey A. Popov, Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Andreas Hirsch, Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Steven H. Strauss, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Olga V. Boltalina, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorMax von Delius
Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Search for more papers by this authorProf. Lothar Dunsch
Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Search for more papers by this authorProf. Oren P. Anderson
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorCorresponding Author
Prof. Dr. Andreas Hirsch
Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Alexey A. Popov, Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Andreas Hirsch, Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Steven H. Strauss, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Olga V. Boltalina, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorCorresponding Author
Prof. Steven H. Strauss
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Alexey A. Popov, Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Andreas Hirsch, Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Steven H. Strauss, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Olga V. Boltalina, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorCorresponding Author
Dr. Olga V. Boltalina
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Alexey A. Popov, Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)
Andreas Hirsch, Friedrich-Alexander-Universität Erlangen-Nürnberg, Lehrstuhl für Organische Chemie II, Henkestrasse 42, 91054 Erlangen (Germany)
Steven H. Strauss, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Olga V. Boltalina, Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1) 970-491-1801
Search for more papers by this authorThis research was supported by the U.S. National Science Foundation (grant no. CHE-1012468).
Graphical Abstract
Gestapelt wie Pappbecher: Moleküle des ersten strukturell aufgeklärten (C59N)2-Derivats, das Trifluormethyl-Gruppen trägt, stapeln mit einem Abstand von 10.179 Å senkrecht aufeinander und bilden so eine seltene, nicht dicht gepackte Anordnung (AAA…︁; siehe Bild). Die Gegenwart von Stickstoff im Fulleren-Grundgerüst führt zu einzigartigen Additionsmustern in C59N(CF3)7/9/11.
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References
- 1J. C. Hummelen, B. Knight, J. Pavlovich, R. Gonzalez, F. Wudl, Science 1995, 269, 1554–1556.
- 2B. Nuber, A. Hirsch, Chem. Commun. 1996, 1421–1422.
- 3O. Vostrowsky, A. Hirsch, Chem. Rev. 2006, 106, 5191–5207.
- 4M. M. Roubelakis, G. C. Vougioukalakis, L. C. Nye, T. Drewello, M. Orfanopoulos, Tetrahedron 2010, 66, 9363–9369.
- 5A. A. Popov, I. E. Kareev, N. B. Shustova, E. B. Stukalin, S. F. Lebedkin, K. Seppelt, S. H. Strauss, O. V. Boltalina, L. Dunsch, J. Am. Chem. Soc. 2007, 129, 11551–11568.
- 6I. E. Kareev, N. B. Shustova, I. V. Kuvychko, S. F. Lebedkin, S. M. Miller, O. P. Anderson, A. A. Popov, S. H. Strauss, O. V. Boltalina, J. Am. Chem. Soc. 2006, 128, 12268–12280.
- 7U. Reuther, A. Hirsch, Chem. Commun. 1998, 1401–1402.
- 8Crystal data for C59N(CF3)5: Mr=1067.65 g mol−1, orthorhombic, Pbca, a=20.0148(5), b=17.3007(5), c=20.3568(5) Å, V=7048.9(3) Å, Z=8, T=100(2) K, 50 290 reflections, 10 755 independent reflections, 726 parameters, R1(I>2s(I))=0.0505, wR2=0.1492, Bruker KappaAPEX II CCD diffractometer (MoKa=0.71073 Å; graphite monochromator). A semiempirical absorption correction was applied using SADABS. The structure was refined using SHELTXL (see also the Supporting Information). CCDC 794474 contains the supplementary crystallographic data for C59N(CF3)5. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- 9A. F. Wells, Structural Inorganic Chemistry, Clarendon Press / Oxford University Press, Oxford, 1984.
- 10S. I. Troyanov, A. A. Popov, N. I. Denisenko, O. V. Boltalina, L. N. Sidorov, E. Kemnitz, Fullerenes Nanotubes Carbon Nanostruct. 2003, 11, 61–77.
- 11I. V. Kuvychko, A. A. Streletskii, N. B. Shustova, K. Seppelt, T. Drewello, A. A. Popov, S. H. Strauss, O. V. Boltalina, J. Am. Chem. Soc. 2010, 132, 6443–6462.
- 12H.-B. Bürgi, E. Blanc, D. Schwarzenbach, S. Liu, Y. Lu, M. M. Kappes, J. A. Ibers, Angew. Chem. 1992, 104, 667–669; Angew. Chem. Int. Ed. Engl. 1992, 31, 640–643.
- 13F. M. Bashilov, B. L. Tumanskii, P. V. Petrovskii, V. I. Sokolov, Tetrahedron 2008, 64, 11291–11293.
- 14R. D. Kennedy, A. L. Ayzner, D. D. Wanger, C. T. Day, M. Halim, S. I. Khan, S. H. Tolbert, B. J. Schwartz, Y. Rubin, J. Am. Chem. Soc. 2008, 130, 17290–17291.
- 15M. Sawamura, K. Kawai, Y. Matsuo, K. Kanie, T. Kato, E. Nakamura, Nature 2002, 419, 702–705.
- 16C.-Z. Li, Y. Matsuo, T. Niinomi, Y. Sato, E. Nakamura, Chem. Commun. 2010, 46, 8582–8584.
- 17R. Rapta, A. Bartl, A. Gromov, A. Stasko, L. Dunsch, ChemPhysChem 2002, 3, 351–356.
10.1002/1439-7641(20020415)3:4<351::AID-CPHC351>3.0.CO;2-W CAS PubMed Web of Science® Google Scholar
- 18N. A. Omelyanyuk, A. A. Goryunkov, N. B. Tamm, S. M. Avdoshenko, I. N. Ioffe, L. N. Sidorov, E. Kemnitz, S. Troyanov, Chem. Commun. 2007, 4794–4796.
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