Fluoride binding by an anionic receptor: tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition

Claudia Caltagirone; Riccardo Montis; Vito Lippolis; Andrea Bencini; Luca Conti; Claudia Giorgi; Peter Horton; Simon Coles; Lucy K Mapp; Philip A. Gale; Luca Fusaro

doi:10.1039/c8cc09962f

Fluoride binding by an anionic receptor: tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition

Claudia Caltagirone, Riccardo Montis, Vito Lippolis, Andrea Bencini, Luca Conti, Claudia Giorgi, Peter Horton, Simon Coles, Lucy K Mapp, Philip A. Gale, Luca Fusaro

Namur Institute of Structured Matter

Research output: Contribution to journal › Article › peer-review

Abstract

Here we report a family of bis-amide receptors for anion binding that contain carboxylic acid groups vicinal to the amide function. Deprotonation of the carboxylic acids decreases the acidity of amide NHs, switching on the anion binding ability of the deprotonated receptors with selectivity for fluoride complexation. The proposed systems represent a unique example of anionic receptors able to bind anions via H-bonding.

Original language	English
Pages (from-to)	2745-2748
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	19
DOIs	https://doi.org/10.1039/c8cc09962f
Publication status	Published - 1 Jan 2019

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10.1039/c8cc09962f

http://dx.doi.org/10.1039/C8CC09962F

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title = "Fluoride binding by an anionic receptor: tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition",

abstract = "Here we report a family of bis-amide receptors for anion binding that contain carboxylic acid groups vicinal to the amide function. Deprotonation of the carboxylic acids decreases the acidity of amide NHs, switching on the anion binding ability of the deprotonated receptors with selectivity for fluoride complexation. The proposed systems represent a unique example of anionic receptors able to bind anions via H-bonding.",

author = "Claudia Caltagirone and Riccardo Montis and Vito Lippolis and Andrea Bencini and Luca Conti and Claudia Giorgi and Peter Horton and Simon Coles and Mapp, {Lucy K} and Gale, {Philip A.} and Luca Fusaro",

note = "Funding Information: The authors thank Fondazione Banco di Sardegna and Regione Autonoma della Sardegna (Progetti Biennali di Ateneo Annualit{\`a}2016; Master and Back program). PAG thanks the Australian Research Council (DP180100612) for funding. Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2019",

month = jan,

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doi = "10.1039/c8cc09962f",

language = "English",

volume = "55",

pages = "2745--2748",

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T1 - Fluoride binding by an anionic receptor

T2 - tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition

AU - Caltagirone, Claudia

AU - Montis, Riccardo

AU - Lippolis, Vito

AU - Bencini, Andrea

AU - Conti, Luca

AU - Giorgi, Claudia

AU - Horton, Peter

AU - Coles, Simon

AU - Mapp, Lucy K

AU - Gale, Philip A.

AU - Fusaro, Luca

N1 - Funding Information: The authors thank Fondazione Banco di Sardegna and Regione Autonoma della Sardegna (Progetti Biennali di Ateneo Annualità2016; Master and Back program). PAG thanks the Australian Research Council (DP180100612) for funding. Publisher Copyright: © 2019 The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Here we report a family of bis-amide receptors for anion binding that contain carboxylic acid groups vicinal to the amide function. Deprotonation of the carboxylic acids decreases the acidity of amide NHs, switching on the anion binding ability of the deprotonated receptors with selectivity for fluoride complexation. The proposed systems represent a unique example of anionic receptors able to bind anions via H-bonding.

AB - Here we report a family of bis-amide receptors for anion binding that contain carboxylic acid groups vicinal to the amide function. Deprotonation of the carboxylic acids decreases the acidity of amide NHs, switching on the anion binding ability of the deprotonated receptors with selectivity for fluoride complexation. The proposed systems represent a unique example of anionic receptors able to bind anions via H-bonding.

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U2 - 10.1039/c8cc09962f

DO - 10.1039/c8cc09962f

M3 - Article

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EP - 2748

JO - Chemical Communications

JF - Chemical Communications

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Fluoride binding by an anionic receptor: tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition

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Fluoride binding by an anionic receptor: tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition

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