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A Musclelike [2](2)Rotaxane: Synthesis, Performance, and Molecular Dynamics Simulations
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1763-9383
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2014 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 79, no 15, 6996-7004 p.Article in journal (Refereed) Published
Abstract [en]

A novel bistable symmetric [2](2)rotaxane was prepared by a threading-followed-by-stoppering strategy and characterized with H-1, C-13, and 2D ROESY NMR spectroscopy and HR-ESI spectrometry. The symmetric [2] (2)rotaxane system consists of an anthracene-based bis(crown ether) as macrocycles, and each of the two dibenzo[24]crown-8 (DB24C8) rings is threaded by the pendant substituents a symmetrically substituted central rotatable ferrocene subunit that possesses two distinguishable recognition sites for the DB24C8 ring: namely, a dibenzylammonium site and an N-methyltriazolium site. The uniform shuttling motion of the thread relative to the two DB24C8 rings in [2](2)rotaxane can be driven by external acid base stimuli, which was evidenced by H-1 and 2D ROESY NMR spectroscopy. Furthermore, molecular dynamics simulations of the [2](2)rotaxane were carried out both in protonated (stretched) and in neutral (contracted) forms. The calculated percentage change in molecular length of the [2](2)rotaxane between the two end-capping bis(methoxyl)phenyl groups is about 48% in the two different states (in acetone), which is much larger than the percentage change (similar to 27%) in human muscle. Moreover, in the two states, the C*-Cp-Cp-C* dihedral angles are computed as -177 degrees in the stretched state and -112 degrees in the contracted state, indicating a correlation between the translational and rotational motions of the [2](2)rotaxane.

Place, publisher, year, edition, pages
2014. Vol. 79, no 15, 6996-7004 p.
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Chemical Sciences
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URN: urn:nbn:se:kth:diva-150527DOI: 10.1021/jo501127hISI: 000339983300022Scopus ID: 2-s2.0-84905383823OAI: oai:DiVA.org:kth-150527DiVA: diva2:746294
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QC 20140912

Available from: 2014-09-12 Created: 2014-09-05 Last updated: 2017-12-05Bibliographically approved

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Li, XinÅgren, Hans

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