Straightforward metal-free synthesis of an azacalix[6]arene forming a host–guest complex with fullerene C 60

Zhongrui Chen (1) , Gabriel Canard (1) , Cloé Azarias (2) , Denis Jacquemin (2) , Olivier Siri (1)

1 CINaM - Centre Interdisciplinaire de Nanoscience de Marseille
2 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

Electronic Supplementary Information (ESI) available: Details of the TD-DFT calculations, NMR spectra of 3b and 4b, preliminary spectrophotometric titration experiments. See a Contrasting with the well mastered azacalix[4]arene, the synthesis and characterization of azacalix[6]arene derivatives remains a challenge for chemists. In this framework, bulky n-octylamino groups appended on the 1,3-meta-diaminobenzene 2b can lead to the concomittant and straightforward one-pot formation of the azacalix[6]arene 4b and of the thermodynamically favoured azacalix[4]arene 3b through simple consecutive nucleophlic aromatic substitutions. The conformations of 3b and 4b were studied in solution and in the solid state using their molecular structures, their NMR and UV-visible spectra combined with first principle TD-DFT calculations. Preliminay solution experiments show that 4b can form a 1:1 host-guest complex with C60.

Domains: Chemical Sciences; Coordination chemistry

Zhongrui Chen, Gabriel Canard, Cloé Azarias, Denis Jacquemin, Olivier Siri. Straightforward metal-free synthesis of an azacalix[6]arene forming a host–guest complex with fullerene C 60. New Journal of Chemistry, 2017, 41 (13), pp.5284 - 5290. ⟨10.1039/c7nj00697g⟩. ⟨hal-01783783⟩