The role of indolyl substituents in squaramide-based anionophores

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 sub...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-10, Vol.2 (4), p.7981-7986
Main Authors: Picci, Giacomo, Carreira-Barral, Israel, Alonso-Carrillo, Daniel, Busonera, Chiara, Milia, Jessica, Quesada, Roberto, Caltagirone, Claudia
Format: Article
Language:English
Subjects:
Anions
Binding
Stability constants
Transport properties
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Summary: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. 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01444k