Abstract
The threading of a double-calix[6]arene system (4) with dialkylammonium axles (2 and 3) has been investigated in the presence of the ‘superweak’ tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (TFPB) anion. NMR and ESI(+)-mass spectrometry analyses showed that singly and doubly threaded pseudorotaxanes can be stepwise formed under appropriate conditions. The directional threading of an alkylbenzylammonium axle with double-calix[6]arene 4 occurs with an endo-alkyl preference in accordance with the ‘endo-alkyl rule’. DFT calculations confirmed this preference and evidenced that the pseudo[3]rotaxane complexes are characterised by an anti-conformation around the bonds, which led to a spatial divergence of the two calix-cavities.
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