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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, Advance Article
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, Advance Article , DOI: 10.1039/D0OB01085E

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