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Molecules 2017, 22(7), 1078; doi:10.3390/molecules22071078

Effects on Rotational Dynamics of Azo and Hydrazodicarboxamide-Based Rotaxanes

Departamento de Química Orgánica, Facultad de Química, Regional Campus of International Excellence “Campus Mare Nostrum”, Universidad de Murcia, 30100 Murcia, Spain
Initial data presented at the 20th International Electronic Conference on Synthetic Organic Chemistry, ECSOC-20, https://sciforum.net/conference/ecsoc-20/paper/3554, 1–30 November 2016, paper d003.
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Received: 1 June 2017 / Revised: 26 June 2017 / Accepted: 26 June 2017 / Published: 28 June 2017
(This article belongs to the Special Issue ECSOC-20)
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Abstract

The synthesis of novel hydrogen-bonded [2]rotaxanes having two pyridine rings in the macrocycle and azo- and hydrazodicarboxamide-based templates decorated with four cyclohexyl groups is described. The different affinity of the binding sites for the benzylic amide macrocycle and the formation of programmed non-covalent interactions between the interlocked components have an important effect on the dynamic behavior of these compounds. Having this in mind, the chemical interconversion between the azo and hydrazo forms of the [2]rotaxane was investigated to provide a chemically-driven interlocked system enable to switch its circumrotation rate as a function of the oxidation level of the binding site. Different structural modifications were carried out to further functionalize the nitrogen of the pyridine rings, including oxidation, alkylation or protonation reactions, affording interlocked azo-derivatives whose rotation dynamics were also analyzed. View Full-Text
Keywords: template synthesis; hydrogen bonded rotaxanes; pirouetting motion; NMR studies template synthesis; hydrogen bonded rotaxanes; pirouetting motion; NMR studies
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Saura-Sanmartin, A.; Martinez-Espin, J.S.; Martinez-Cuezva, A.; Alajarin, M.; Berna, J. Effects on Rotational Dynamics of Azo and Hydrazodicarboxamide-Based Rotaxanes. Molecules 2017, 22, 1078.

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