Issue 9, 2024

Tetra-azobenzene extended calix[4]pyrroles: influence of photo-isomerization on chloride binding and its transport through liposomal membranes

Abstract

In this work, we report the synthesis of three tetra-azobenzene extended calix[4]pyrroles and describe their photo-isomerization behavior in dichloromethane monitored by UV-Vis and NMR spectroscopies. We study and compare the binding properties of the receptors in their all-trans form and their corresponding photo-stationary state (PSS) cis-enriched mixtures with methyl trioctylammonium chloride (MTOA·Cl) in dichloromethane. Using 1H NMR spectroscopy we probe that all the receptors form 1 : 1 : 1 ion-paired complexes with MTOA·Cl featuring a receptor separated geometry. Moreover, isothermal titration calorimetry (ITC) experiments enabled the accurate determination of the binding constants. Finally, we assess the chloride transport activity of the receptors by pre-inserting them in large unilamellar vesicles. We compare the results derived from the transport experiments with those of the binding studies in solution.

Graphical abstract: Tetra-azobenzene extended calix[4]pyrroles: influence of photo-isomerization on chloride binding and its transport through liposomal membranes

Supplementary files

Article information

Article type
Research Article
Submitted
01 Mar 2024
Accepted
13 Mar 2024
First published
22 Mar 2024
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2024,11, 2468-2476

Tetra-azobenzene extended calix[4]pyrroles: influence of photo-isomerization on chloride binding and its transport through liposomal membranes

P. Ferreira, G. Aragay and P. Ballester, Org. Chem. Front., 2024, 11, 2468 DOI: 10.1039/D4QO00399C

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