Calix[6]arene-based atropoisomeric pseudo[2]rotaxanes
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Published on: March 14, 2025
Carmine Gaeta1, Carmen Talotta1, Placido Neri1
1Dipartimento di Chimica e Biologia " A. Zambelli", Università di Salerno, Via Giovanni Paolo II 132, 84084 Fisciano (Salerno), Italy.
Abstract:
Some examples of atropoisomeric pseudorotaxanes in which the isomerism arises by the different conformations adopted by the wheel are reported here. Upon threading hexahexyloxycalix[6]arene 1 with ammonium axles 2+ or 3+ , bearing biphenyl or trifluoromethylbenzyl moieties, respectively, two atropoisomeric pseudorotaxanes were formed in which the calix[6]-wheel 1 adopts the 1,2,3-alternate and cone conformations. The interconversion between them cannot be obtained by simple rotation around the ArCH2Ar bonds of the calixarene wheel, which is blocked by the presence of the axle inside its cavity. Therefore, it can only be obtained through a mechanism of de-threading/re-threading of the axle. In all the examined cases, the 1,2,3-alternate and cone atropoisomers are, respectively, the kinetic and the thermodynamic ones.
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