Issue 3, 2022
From the journal:

Organic Chemistry Frontiers

Vinyl sulfonyl chemistry-driven unidirectional transport of a macrocycle through a [2]rotaxane†

Arthur H. G. David, ORCID logo a   Pablo García–Cerezo, ORCID logo a   Araceli G. Campaña, ORCID logo a   Francisco Santoyo–González ORCID logo *a  and  Victor Blanco ORCID logo *a  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Ciencias, Unidad de Excelencia de Química Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada (UGR), Avda. Fuente Nueva S/N, 18071 Granada, Spain
E-mail: fsantoyo@ugr.es, victorblancos@ugr.es

Abstract

By applying a combination of the coupling-and-decoupling (CAD) chemistry of the vinyl sulfonate group with the click thia-Michael addition to the vinyl sulfone group (MAVS) we performed the irreversible unidirectional transportation of the ring through the linear component in a [2]rotaxane by a chemically and pH-driven flashing energy ratchet mechanism. The design is based on a monostoppered thread precursor bearing a sulfonate stopper, a vinyl sulfone group on the unstoppered end and a dibenzylammonium unit as recognition site for the dibenzo-24-crown-8 macrocycle. First, the ring enters from the vinyl sulfone side and the rotaxane is capped through a thia-Michael addition reaction. Then, the cleavage of the sulfonate group of the opposite stopper using MgBr2 as chemical stimulus and subsequent addition of base (Et3N) promoted the controlled and directional release of the macrocycle into the bulk under mild conditions. The efficiency of the system allowed the in situ operation as demonstrated by NMR and HRMS techniques.

Graphical abstract: Vinyl sulfonyl chemistry-driven unidirectional transport of a macrocycle through a [2]rotaxane

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Article information

DOI
https://doi.org/10.1039/D1QO01491A
Article type
Research Article
Submitted
05 Oct 2021
Accepted
25 Nov 2021
First published
26 Nov 2021
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2022,9, 633-642

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Vinyl sulfonyl chemistry-driven unidirectional transport of a macrocycle through a [2]rotaxane

A. H. G. David, P. García–Cerezo, A. G. Campaña, F. Santoyo–González and V. Blanco, Org. Chem. Front., 2022, 9, 633 DOI: 10.1039/D1QO01491A

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