Next Article in Journal
Fabrication and Cytotoxicity of Gemcitabine-Functionalized Magnetite Nanoparticles
Next Article in Special Issue
Facile Synthesis of Novel Coumarin Derivatives, Antimicrobial Analysis, Enzyme Assay, Docking Study, ADMET Prediction and Toxicity Study
Previous Article in Journal
Spectroscopic Investigation of the Interaction of the Anticancer Drug Mitoxantrone with Sodium Taurodeoxycholate (NaTDC) and Sodium Taurocholate (NaTC) Bile Salts
Previous Article in Special Issue
Microwave-Assisted Facile Synthesis, Anticancer Evaluation and Docking Study of N-((5-(Substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) Benzamide Derivatives
Article Menu
Issue 7 (July) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(7), 1078;

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,, 1–30 November 2016, paper d003.
Authors to whom correspondence should be addressed.
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)
Full-Text   |   PDF [2042 KB, uploaded 28 June 2017]   |  


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

Graphical abstract

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).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top