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Regio‐, Stereo‐, and Atropselective Synthesis of C 60 Fullerene Bisadducts by Supramolecular‐Directed Functionalization
Author(s) -
Bottari Giovanni,
Trukhina Olga,
Kahnt Axel,
Frunzi Michael,
Murata Yasujiro,
RodríguezFortea Antonio,
Poblet Josep M.,
Guldi Dirk M.,
Torres Tomás
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602713
Subject(s) - surface modification , supramolecular chemistry , fullerene , enantiomer , chirality (physics) , context (archaeology) , chemistry , steric effects , non covalent interactions , combinatorial chemistry , nanotechnology , stereochemistry , materials science , organic chemistry , molecule , physics , biology , paleontology , quark , hydrogen bond , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics
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 C 60 fullerene bisadduct racemate from a complex mixture of 130 bisadducts. Remarkably, both enantiomers, which present a sterically demanding cis ‐1 C 60 addition pattern, represent the first examples of fullerene derivatives which combine central, axial, and helical chirality.