Abstract
Dynamic [1]Rotaxanes via Reversible Covalent Bond
and Host-Guest Anion Recognition
Arico Del Mauro, 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 a type of compound that is widely
used in the construction of artificial molecular machines.1 Among MIMs, the rotaxane
and pseudorotaxane classes are particularly intriguing, consisting of a macrocyclic
wheel threaded by the axle and having numerous applications.2 We recently reported
a novel [2]rotaxane system3 that combines a reversible hypervalent iodine covalent
bond with anion recognition properties of bambus[6]uril macrocycles.
We present racemic mono-functionalized bambus[6]uril appended with a single
aliphatic carboxylate arm [1]rotaxanes(Fig. 1). The arm is forming a
bis(acyloxy)iodate(I) anionic moiety that is threading through the bambus[6]uril cavity.
We investigated the possibility of component exchange to facilitate carboxylic acid
triggered release.4 Furthmore, we create a new enantiomerically pure monofunctionalized
bambus[6]uril and the first enantiomerically pure [1]rotaxanes based
on hypervalent iodine axle. Following that, the [1]rotaxanes will be tested for chiral
carboxylic acid recognition.
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. Chem. Rev. 2015, 115 (18), 10081–10206.
(2) Xue, M.; Yang, Y.; Chi, X.; Yan, X.; Huang, F. Development of
Pseudorotaxanes and Rotaxanes: From Synthesis to Stimuli-Responsive Motions to
Applications. Chem. Rev. 2015, 115 (15), 7398–7501.
(3) Kandrnálová, M.; Kokan, Z.; Havel, V.; Nečas, M.; Šindelář, V. Hypervalent
Iodine Based Reversible Covalent Bond in Rotaxane Synthesis. Angewandte Chemie
International Edition 2019, 58 (50), 18182–18185.
(4) Mauro, A. D.; Kokan, Z.; Šindelář, V. Dynamic [1]Rotaxanes via a Reversible
Covalent Bond and Host–Guest Anion Recognition. Chem. Commun. 2022, 58 (23),
3815-3818.