Abstract
Dynamic [1]Rotaxanes via Reversible Covalent Bond
and Host-Guest Anion Recognition
Arico Del Mauro, Zoran Kokan, and Vladimír Šindelář*
Department of Chemistry and RECETOX, Faculty of Science, Masaryk University,
Kamenice 5, 625 00 Brno, Czech Republic.
e-mail: 503620@mail.muni.cz
Mechanically interlocked molecules (MIMs) are an important class of compounds
used for the construction of artificial molecular machines.1 Within MIMs, rotaxane and
pseudorotaxane classes are especially interesting, comprising a macrocyclic wheel
threaded by the axle, with numerous applications.2 Recently, we have reported a
novel [2]rotaxane system3 coupling hypervalent iodine reversible covalent bond with
anion recognition properties of bambus[6]uril macrocycles.
Herein, we report the [1]rotaxanes consisted of racemic mono-functionalized
bambus[6]uril appended with a single aliphatic carboxylate arm (Fig. 1). The arm is
engaged in the formation of a bis(acyloxy)iodate(I) anionic moiety threading through
the bambus[6]uril cavity. We investigated the possibility of component exchange to
facilitate triggered release of carboxylic acids.
Fig. 1 Representation of the prepared [1]rotaxanes.
This work was supported by the Czech Science Foundation (No. GA20-13922S).
1 Erbas-Cakmak, S.; Leigh, D. A.; McTernan, C. T.; Nussbaumer, A. L. Artificial
Molecular Machines. Chemical Reviews 2015, 115 (18), 10081–10206.
https://doi.org/10.1021/acs.chemrev.5b00146.
2 Xue, M.; Yang, Y.; Chi, X.; Yan, X.; Huang, F. Development of
Pseudorotaxanes and Rotaxanes: From Synthesis to Stimuli-Responsive Motions to
Applications. Chemical Reviews 2015, 115 (15), 7398–7501.
https://doi.org/10.1021/cr5005869.
3 Kandrnálová, M.; Kokan, Z.; Havel, V.; Nečas, M.; Šindelář, V. Hypervalent
Iodine Based Reversible Covalent Bond in Rotaxane Synthesis. Angew. Chem. Int.
Ed. 2019, 58 (50), 18182–18185. https://doi.org/10.1002/anie.201908953.