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Issue 27, 2020
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An electrochemically controlled supramolecular zip tie based on host–guest chemistry of CB[8]

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Abstract

Three molecular threads incorporating two viologen units attached by an oligo-ethylene glycol chain of variable length and an electron rich naphthalene moiety were prepared. The internal viologen unit is connected to the naphthalene by a rigid linker that prevents the simultaneous complexation of these systems. The axle with the shortest chain (14+) in the presence of CB[8] placed the chain inside the macrocycle in aqueous media. In contrast, the longer chains in 24+ and 34+ allow locating the terminal viologen and the electron rich unit inside the cavity. Upon reduction of the bipyridinium salts, the system behaves like a zip tie relaxing the chain as a consequence of the insertion of both radical cation moieties within the CB[8] and making these switches as potential components for molecular machinery.

Graphical abstract: An electrochemically controlled supramolecular zip tie based on host–guest chemistry of CB[8]

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Article information


Submitted
26 May 2020
Accepted
22 Jun 2020
First published
22 Jun 2020

Org. Biomol. Chem., 2020,18, 5228-5233
Article type
Paper

An electrochemically controlled supramolecular zip tie based on host–guest chemistry of CB[8]

I. Neira, O. Domarco, J. L. Barriada, P. Franchi, M. Lucarini, M. D. García and C. Peinador, Org. Biomol. Chem., 2020, 18, 5228
DOI: 10.1039/D0OB01085E

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