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+) 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)]
Original language | English |
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Pages (from-to) | 2754-2760 |
Number of pages | 7 |
Journal | Organic & Biomolecular Chemistry |
Volume | 12 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2014 |
Externally published | Yes |
Keywords
- host guest chem calixarene aza cryptand crystallog NMR
- conformational inversion host guest chem calixarene aza cryptand heat
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CCDC 985920: Experimental Crystal Structure Determination
Brugnara, A. (Contributor), Colasson, B. (Contributor), Fusaro, L. (Contributor), Luhmer, M. (Contributor), Prangé, T. (Contributor) & Reinaud, O. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 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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