A covalent organic cage compound acting as a supramolecular shadow mask for the regioselective functionalization of C60

Viktoria Leonhardt; Stefanie Fimmel; Ana-Maria Krause; Florian Beuerle

doi:10.1039/D0SC03131C

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A covalent organic cage compound acting as a supramolecular shadow mask for the regioselective functionalization of C₆₀†‡

Viktoria Leonhardt,^ab Stefanie Fimmel,^b Ana-Maria Krause^ab and Florian Beuerle

*^ab

Author affiliations

* Corresponding authors

^a Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg, Germany
E-mail: florian.beuerle@uni-wuerzburg.de

^b Universität Würzburg, Center for Nanosystems Chemistry (CNC), Bavarian Polymer Institute (BPI), Theodor-Boveri-Weg, 97074 Würzburg, Germany

Abstract

A trigonal-bipyramidal covalent organic cage compound serves as an efficient host to form stable 1 : 1-complexes with C₆₀ and C₇₀. Fullerene encapsulation has been comprehensively studied by NMR and UV/Vis spectroscopy, mass spectrometry as well as single-crystal X-ray diffraction. Exohedral functionalization of encapsulated C₆₀via threefold Prato reaction revealed high selectivity for the symmetry-matched all-trans-3 addition pattern.

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Article information

DOI: https://doi.org/10.1039/D0SC03131C
Article type: Edge Article
Submitted: 04 Jun 2020
Accepted: 06 Jul 2020
First published: 07 Jul 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2020,11, 8409-8415

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A covalent organic cage compound acting as a supramolecular shadow mask for the regioselective functionalization of C₆₀

V. Leonhardt, S. Fimmel, A. Krause and F. Beuerle, Chem. Sci., 2020, 11, 8409 DOI: 10.1039/D0SC03131C

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