Regio-, Stereo-, and Atropselective Synthesis of C60 Fullerene Bisadducts by Supramolecular-Directed Functionalization
Corresponding Author
Dr. Giovanni Bottari
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain
IMDEA-Nanociencia, Campus de Cantoblanco, 28049 Madrid, Spain
Search for more papers by this authorDr. Olga Trukhina
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain
IMDEA-Nanociencia, Campus de Cantoblanco, 28049 Madrid, Spain
Search for more papers by this authorDr. Axel Kahnt
Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany
Search for more papers by this authorDr. Michael Frunzi
Department of Chemistry, Columbia University, New York, NY, 10027 USA
Search for more papers by this authorProf. Dr. Yasujiro Murata
Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011 Japan
Search for more papers by this authorDr. Antonio Rodríguez-Fortea
Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, 43007 Tarragona, Spain
Search for more papers by this authorProf. Dr. Josep M. Poblet
Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, 43007 Tarragona, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Dirk M. Guldi
Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Tomás Torres
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain
IMDEA-Nanociencia, Campus de Cantoblanco, 28049 Madrid, Spain
Search for more papers by this authorCorresponding Author
Dr. Giovanni Bottari
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain
IMDEA-Nanociencia, Campus de Cantoblanco, 28049 Madrid, Spain
Search for more papers by this authorDr. Olga Trukhina
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain
IMDEA-Nanociencia, Campus de Cantoblanco, 28049 Madrid, Spain
Search for more papers by this authorDr. Axel Kahnt
Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany
Search for more papers by this authorDr. Michael Frunzi
Department of Chemistry, Columbia University, New York, NY, 10027 USA
Search for more papers by this authorProf. Dr. Yasujiro Murata
Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011 Japan
Search for more papers by this authorDr. Antonio Rodríguez-Fortea
Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, 43007 Tarragona, Spain
Search for more papers by this authorProf. Dr. Josep M. Poblet
Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, 43007 Tarragona, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Dirk M. Guldi
Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Tomás Torres
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain
IMDEA-Nanociencia, Campus de Cantoblanco, 28049 Madrid, Spain
Search for more papers by this authorAbstract
The regio- and stereocontrolled synthesis of fullerene bisadducts is a topic of increasing interest in fullerene chemistry and a key point for the full exploitation of these derivatives in materials science. In this context, while the tether-directed remote functionalization strategy offers a valid approach to this synthetic challenge, no examples of such control have yet been reported using nontethered species. Presented here is a conceptually novel, supramolecular-directed functionalization approach in which noncovalent interactions between untethered residues have been used, for the first time, to amplify (>2800-fold) the regio-, stereo-, and atropselective formation of a C60 fullerene bisadduct racemate from a complex mixture of 130 bisadducts. Remarkably, both enantiomers, which present a sterically demanding cis-1 C60 addition pattern, represent the first examples of fullerene derivatives which combine central, axial, and helical chirality.
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