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

Andrea Brugnara, Luca Fusaro, Michel Luhmer, Thierry Prange, Benoit Colasson, Olivia. Reinaud

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)2754-2760
Number of pages7
JournalOrganic & Biomolecular Chemistry
Volume12
Issue number17
DOIs
Publication statusPublished - 2014
Externally publishedYes

Keywords

  • host guest chem calixarene aza cryptand crystallog NMR
  • conformational inversion host guest chem calixarene aza cryptand heat

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