Issue 17, 2014

An induced-fit process through mechanical pivoting of aromatic walls in host–guest chemistry of calix[6]arene aza-cryptands

Abstract

The per-ipso-nitration of a TMPA-capped calix[6]arene has been achieved. The substitution of the six bulky tBu substituents for nitro groups has a strong impact on the behavior of the ligand during guest recognition. The complexation of the aza cap (by H+ or Cu+) associated with the encapsulation of a guest triggers an induced-fit process leading to the loss of the cone conformation of the host in favor of alternate conformations. Such a “pivoting” response of one or two walls of the calixarene core induces a large mechanical motion of the corresponding aromatic units. This stands in strong contrast with the “breathing” phenomena previously identified with other calix[6]arene-based complexes that expand or shrink the size of their cone as a function of the guest. Because of the covalently attached rigid TMPA cap, three arene units of this new calixarene host have a restricted mobility, which forces it to respond in a different manner to a supramolecular stress.

Graphical abstract: An induced-fit process through mechanical pivoting of aromatic walls in host–guest chemistry of calix[6]arene aza-cryptands

Supplementary files

Article information

Article type
Paper
Submitted
10 Feb 2014
Accepted
27 Feb 2014
First published
27 Feb 2014

Org. Biomol. Chem., 2014,12, 2754-2760

Author version available

An induced-fit process through mechanical pivoting of aromatic walls in host–guest chemistry of calix[6]arene aza-cryptands

A. Brugnara, L. Fusaro, M. Luhmer, T. Prangé, B. Colasson and O. Reinaud, Org. Biomol. Chem., 2014, 12, 2754 DOI: 10.1039/C4OB00304G

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