Résumé
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+) assocd. 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 mech. motion of the corresponding arom. 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 supramol. stress. [on SciFinder(R)]
langue originale | Anglais |
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Pages (de - à) | 2754-2760 |
Nombre de pages | 7 |
journal | Organic & Biomolecular Chemistry |
Volume | 12 |
Numéro de publication | 17 |
Les DOIs | |
Etat de la publication | Publié - 2014 |
Modification externe | Oui |
Empreinte digitale
Examiner les sujets de recherche de « An induced-fit process through mechanical pivoting of aromatic walls in host-guest chemistry of calix[6]arene aza-cryptands. ». Ensemble, ils forment une empreinte digitale unique.Ensembles de données
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CCDC 985920: Experimental Crystal Structure Determination
Brugnara, A. (Contributeur), Colasson, B. (Contributeur), Fusaro, L. (Contributeur), Luhmer, M. (Contributeur), Prangé, T. (Contributeur) & Reinaud, O. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2014
DOI: 10.5517/cc122xwy, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc122xwy&sid=DataCite
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