Intertwined Detection and Recognition Roles of Tetrazine in Synergistic Anion‐π and H‐bond Based Anion Receptor

Plais, Romain; Gouarin, Guy; Gaucher, Anne; Haldys, Violette; Brosseau, Arnaud; Clavier, Gilles; Salpin, Jean‐Yves; Prim, Damien

doi:10.1002/cphc.202000289

Cited by 8 publications

(47 citation statements)

References 33 publications

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“…Note that such doubly-charged complexes could not be observed with the smaller anion receptor 1. 27 We then tried to obtain structural information about the [(2) n -X] À anions. Starting with [(2) 2 -X] À species, their unimolecular dissociation upon collision induced dissociation (CID) is solely characterized by the elimination of the intact receptor 2 (presently illustrated by Fig.…”

Section: Tandem Mass Spectrometrymentioning

confidence: 99%

“…These results are in line with our previous publications. 23,27 UV-visible spectra measured during the titration of 2 with chloride anion are reported in Fig. 5.…”

Section: Photophysical Analysis: Excited State Binding Studiesmentioning

confidence: 99%

“…35,36 Only one aliphatic mono-substituted tetrazine receptor has been recently reported by us. 27 The impact of a double substitution on receptor properties was therefore evaluated based on descriptors such as (a) geometrical parameters (b) NMR shis (c) photophysical properties and (d) association constants determined by NMR experiments.…”

Section: Impact Of Double-substitution On Receptor Propertiesmentioning

confidence: 99%

“…25,26 We recently showed that photophysical properties are particularly useful to characterize anion complexes in solution in a new anion receptor (1) combining a tetrazine and an urea subunits linked by a short exible arm. 27 Examination of the receptor 1 shows that an extra position is available at the tetrazine core for installing an additional urea motif (Scheme 1). We hypothesized that a second nucleophilic aromatic substitution (S N Ar) would enable access to a new family of anion receptors.…”

Section: Introductionmentioning

confidence: 99%

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Design and property investigation on a five-interaction-based fluorescent anion receptor clip

et al. 2021

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Section: Tandem Mass Spectrometrymentioning

confidence: 99%

“…These results are in line with our previous publications. 23,27 UV-visible spectra measured during the titration of 2 with chloride anion are reported in Fig. 5.…”

Section: Photophysical Analysis: Excited State Binding Studiesmentioning

confidence: 99%

Section: Impact Of Double-substitution On Receptor Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design and property investigation on a five-interaction-based fluorescent anion receptor clip

et al. 2021

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“…In the quest for more efficient anion receptors, several studies have employed the use of hydrogen bonding donor molecules in conjunction with other functional systems, like polysubstituted benzene rings. For instance, squaramides, [5] urea, [6,7] pyrrole, [8] and other nitrogen heterocycle compounds [9] are among the most common building blocks to construct anion receptors.…”

Section: Introductionmentioning

confidence: 99%

Understanding the Chloride Affinity of Barbiturates for Anion Receptor Design

et al. 2021

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Due to their potential binding sites, barbituric acid (BA) and its derivatives have been used in metal coordination chemistry. Yet their abilities to recognize anions remain unexplored. In this work, we were able to identify four structural features of barbiturates that are responsible for a certain anion affinity. The set of coordination interactions can be finely tuned with covalent decorations at the methylene group. DFT‐D computations at the BLYP‐D3(BJ)/aug‐cc‐pVDZ level of theory show that the C−H bond is as effective as the N−H bond to coordinate chloride. An analysis of the electron charge density at the C−H⋅⋅⋅Cl− and N−H⋅⋅⋅Cl− bond critical points elucidates their similarities in covalent character. Our results reveal that the special acidity of the C−H bond shows up when the methylene group moves out of the ring plane and it is mainly governed by the orbital interaction energy. The amide and carboxyl groups are the best choices to coordinate the ion when they act together with the C−H bond. We finally show how can we use this information to rationally improve the recognition capability of a small cage‐like complex that is able to coordinate NaCl.

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Chloride Binding Modulated by Anion Receptors Bearing Tetrazine and Urea

et al. 2022

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Modulation and fine‐tuning of the strength of weak interactions to bind anions are described in a series of synthetic receptors. The general design of the receptors includes both a urea motif and a tetrazine motif. The synthetic sequence towards three receptors is detailed. Impacts of H‐bond strength and linker length between urea and tetrazine on chloride complexation are studied. Binding properties of the chloride anion are examined in both the ground and excited states using a panel of analytical methods (NMR spectroscopy, mass spectrometry, UV/Visible spectroscopies, and fluorescence). A ranking of the receptors by complexation strength has been determined, allowing a better understanding of the structure‐properties relationship on these compounds.

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Intertwined Detection and Recognition Roles of Tetrazine in Synergistic Anion‐π and H‐bond Based Anion Receptor

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 8 publications

References 33 publications

Design and property investigation on a five-interaction-based fluorescent anion receptor clip

Design and property investigation on a five-interaction-based fluorescent anion receptor clip

Understanding the Chloride Affinity of Barbiturates for Anion Receptor Design

Chloride Binding Modulated by Anion Receptors Bearing Tetrazine and Urea

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