ABSTRACT
The synthesis of a [2]rotaxane, comprising a calix[6]arene-wheel and a dibenzyl-ammonium axle, is here reported. By virtue of its inherent directionality, the calix-wheel makes non-degenerate two equivalent stations of the symmetrical axle. In this way, the neutral rotaxane shows two co-conformations, named endo-alkyl and endo-benzyl, in which an alkyl or benzyl moiety of the axle are included inside the calix-cavity, respectively. NMR and DFT studies showed that the co-conformation preferred by the neutral mechanomolecule is the ‘endo-alkyl’ one, which is more stabilized by C-H···π interactions between the included alkyl chain and the aromatic wall of the calix-cavity.
Graphical Abstract
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Acknowledgments
The authors acknowledge the Regione Campania (POR CAMPANIA FESR 2007/2013 O.O.2.1, CUP B46D14002660009) for the FT-ICR mass spectrometer facilities, Farma-BioNet (CUP B25C13000230007), the Centro di Tecnologie Integrate per la Salute” (CITIS) (project PONa3_00138) for the 600 MHz NMR facilities and Università di Salerno for financial support.
Disclosure statement
No potential conflict of interest was reported by the authors.
Supplementary material
Supplemental data for this article can be accessed here.