In:
Angewandte Chemie, Wiley, Vol. 128, No. 37 ( 2016-09-05), p. 11186-11191
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 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.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v128.37
DOI:
10.1002/ange.201602713
Language:
English
Publisher:
Wiley
Publication Date:
2016
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