Issue 40, 2022

The role of indolyl substituents in squaramide-based anionophores

Abstract

A new family of squaramide-based anionophores (L1–L8) have been synthesised and fully characterised with the aim to investigate the effect of indolyl substituents on their anion binding and transmembrane transport properties. L1, L2, L6, and L8, bearing a 7-indolyl/indol-7-yl moiety as the substituent, were found to be the most efficient of the series in binding chloride with high stability constants. L1, L6, and L8 were also found to be the most potent anionophores of the series, able to mediate transmembrane anion transport. In particular, L6 bearing the 3,5-bis(trifluoromethyl)phenyl group was found to be the most active transporter, and its efficiency as an anionophore/anion transporter was favourably compared with that of their symmetrically-substituted squaramide analogues L9 and L10, previously reported in the literature.

Graphical abstract: The role of indolyl substituents in squaramide-based anionophores

Supplementary files

Article information

Article type
Paper
Submitted
08 Aug 2022
Accepted
23 Sep 2022
First published
23 Sep 2022
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2022,20, 7981-7986

The role of indolyl substituents in squaramide-based anionophores

G. Picci, I. Carreira-Barral, D. Alonso-Carrillo, C. Busonera, J. Milia, R. Quesada and C. Caltagirone, Org. Biomol. Chem., 2022, 20, 7981 DOI: 10.1039/D2OB01444K

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