Publication: Modulating the shuttling motion of [2]rotaxanes built of p-xylylenediamine units through permethylation at the benzylic positions of the ring
Authors
Puigcerver, Julio ; Alajarín, Mateo ; Berna, José ; Martínez Cuezva, Alberto
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Publisher
Royal Society of Chemistry
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Description
© The Royal Society of Chemistry 2023. This manuscript version is made available under the CC-BY-NC 4.0 license http://creativecommons.org/licenses/by-nc/4.0/. This document is the Published version of a Published Work that appeared in final form in Organic and Biomolecular Chemistry. To access the final edited and published work see https://doi.org/10.1039/D3OB01611K
Abstract
In this study, we show the effect of the gem-dimethyl substitution at the four benzylic carbons of the ring on the internal dynamics of two-station [2]rotaxanes. Such structural modification of the polyamide macrocycles promotes a drastic change of the internal dynamics as shown by variable-temperature (VT) 1H NMR experiments. We determined that the shuttling rates of the octamethylated macrocycle along a series of symmetrical threads were significantly faster compared to the non-substituted ring. This effect was particulary pronounced in the -based system, in which the rate was 27 times faster than that of the model system.
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