title: Regio-, Stereo-, and Atropselective Synthesis of C60 Fullerene Bisadducts by Supramolecular-Directed Functionalization.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049, Madrid, Spain. giovanni.bottari@uam.es.|IMDEA-Nanociencia, Campus de Cantoblanco, 28049, Madrid, Spain. giovanni.bottari@uam.es.
authors.forename: Giovanni
authors.identifier: 0000-0001-6141-7027
authors.initials: G
authors.lastname: Bottari
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049, Madrid, Spain.|IMDEA-Nanociencia, Campus de Cantoblanco, 28049, Madrid, Spain.
authors.forename: Olga
authors.initials: O
authors.lastname: Trukhina
authors.affiliation: Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058, Erlangen, Germany.
authors.forename: Axel
authors.initials: A
authors.lastname: Kahnt
authors.affiliation: Department of Chemistry, Columbia University, New York, NY, 10027, USA.
authors.forename: Michael
authors.initials: M
authors.lastname: Frunzi
authors.affiliation: Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011, Japan.
authors.forename: Yasujiro
authors.initials: Y
authors.lastname: Murata
authors.affiliation: Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, 43007, Tarragona, Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Rodríguez-Fortea
authors.affiliation: Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, 43007, Tarragona, Spain.
authors.forename: Josep M
authors.initials: JM
authors.lastname: Poblet
authors.affiliation: Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058, Erlangen, Germany. dirk.guldi@fau.de.
authors.forename: Dirk M
authors.initials: DM
authors.lastname: Guldi
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049, Madrid, Spain. tomas.torres@uam.es.|IMDEA-Nanociencia, Campus de Cantoblanco, 28049, Madrid, Spain. tomas.torres@uam.es.
authors.forename: Tomás
authors.initials: T
authors.lastname: Torres
keywords: atropisomerism; cycloaddition; fullerenes; phthalocyanines; supramolecular chemistry