Regio-, Stereo-, and Atropselective Synthesis of C60Fullerene Bisadducts by Supramolecular-Directed Functionalization

Bottari G, Trukhina O, Kahnt A, Frunzi M, Murata Y, Rodriguez-Fortea A, Poblet JM, Guldi DM, Torres T (2016)

Publication Type: Journal article

Publication year: 2016

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 55

Pages Range: 11020-11025

Journal Issue: 37

DOI: 10.1002/anie.201602713

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 C60fullerene bisadduct racemate from a complex mixture of 130 bisadducts. Remarkably, both enantiomers, which present a sterically demanding cis-1 C60addition pattern, represent the first examples of fullerene derivatives which combine central, axial, and helical chirality.

Authors with CRIS profile

Axel Kahnt Lehrstuhl für Physikalische Chemie I Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Universidad Autónoma de Madrid (UAM) ES Spain (ES) Columbia University US United States (USA) (US) Kyoto University / 京都大学 Kyōto daigaku JP Japan (JP) Universitat Rovira i Virgili (URV) ES Spain (ES)

How to cite

APA:

Bottari, G., Trukhina, O., Kahnt, A., Frunzi, M., Murata, Y., Rodriguez-Fortea, A.,... Torres, T. (2016). Regio-, Stereo-, and Atropselective Synthesis of C60Fullerene Bisadducts by Supramolecular-Directed Functionalization. Angewandte Chemie International Edition, 55(37), 11020-11025. https://doi.org/10.1002/anie.201602713

MLA:

Bottari, Giovanni, et al. "Regio-, Stereo-, and Atropselective Synthesis of C60Fullerene Bisadducts by Supramolecular-Directed Functionalization." Angewandte Chemie International Edition 55.37 (2016): 11020-11025.

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