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Issue 13, 2017
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Straightforward metal-free synthesis of an azacalix[6]arene forming a host–guest complex with fullerene C60

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Abstract

Contrasting with the well mastered azacalix[4]arene, the synthesis and characterization of azacalix[6]arene derivatives remain a challenge for chemists. In this framework, bulky n-octylamino groups appended on 1,3-meta-diaminobenzene 2b can lead to the concomitant and straightforward one-pot formation of azacalix[6]arene 4b and of the thermodynamically favoured azacalix[4]arene 3b through simple consecutive nucleophilic aromatic substitutions. The conformations of 3b and 4b were studied in solution and in the solid state using their X-ray molecular structures, their NMR and UV-Visible spectra combined with first principles TD-DFT calculations. Preliminary solution experiments show that 4b can form a 1 : 1 host–guest complex with C60.

Graphical abstract: Straightforward metal-free synthesis of an azacalix[6]arene forming a host–guest complex with fullerene C60

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Publication details

The article was received on 28 Feb 2017, accepted on 23 May 2017 and first published on 23 May 2017


Article type: Paper
DOI: 10.1039/C7NJ00697G
Citation: New J. Chem., 2017,41, 5284-5290
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    Straightforward metal-free synthesis of an azacalix[6]arene forming a host–guest complex with fullerene C60

    Z. Chen, G. Canard, C. Azarias, D. Jacquemin and O. Siri, New J. Chem., 2017, 41, 5284
    DOI: 10.1039/C7NJ00697G

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