Facile access to functional building blocks of C60 involving C3-symmetrical addition patterns

Gmehling A, Hirsch A (2013)


Publication Type: Journal article, Original article

Publication year: 2013

Journal

Original Authors: Gmehling A., Hirsch A.

Publisher: Wiley-VCH Verlag

Pages Range: 5093-5105

Journal Issue: 23

DOI: 10.1002/ejoc.201300482

Abstract

A new class of C-symmetrical fullerene building blocks with a well-defined spatial arrangement of addends has been developed. They comprise compounds with a e,e,e-trisaddition pattern and a mixed octahedral hexakisaddition pattern. Fullerenophosphates with a e,e,e-addition pattern were used for the spatial preorganization of the addends. After deprotection seven different trisbromides (12-16, 15a, 16a) with varying chain lengths and orientation of the functional groups were obtained. Acetylenes could be coupled to these compounds by click chemistry through an intermediate trisazide. For the synthesis of mixed hexakisadducts 19-21 a template system based on a central benzyl moiety was attached to the free hemisphere of the trisadduct fullerenophosphates. It was shown that the phosphate and the benzyl template can be removed independently. Fully deprotected building block 24 bearing both terminal bromide and hydroxy moieties was prepared. In addition, rather complex hybrid architecture 29 bearing three porphyrin units in the polar addend zone was successfully synthesized. A strategy that exploits the C- symmetrical preorganization of fullerenophosphates to create fullerenes that may be functionalized is described. Both e,e,e-trisadducts and mixed hexakisadducts are presented. The fullerenophosphates can easily be transferred into bromides, azides and triazolines by using click chemistry. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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How to cite

APA:

Gmehling, A., & Hirsch, A. (2013). Facile access to functional building blocks of C60 involving C3-symmetrical addition patterns. European Journal of Organic Chemistry, 23, 5093-5105. https://dx.doi.org/10.1002/ejoc.201300482

MLA:

Gmehling, Alexander, and Andreas Hirsch. "Facile access to functional building blocks of C60 involving C3-symmetrical addition patterns." European Journal of Organic Chemistry 23 (2013): 5093-5105.

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