Anion‐Dependent Switching: Dynamically Controlling the Conformation of Hydrogen‐Bonded Diphenylacetylenes

Jones, Ian M.; Hamilton, Andrew D.

doi:10.1002/ange.201100144

Cited by 25 publications

(11 citation statements)

References 41 publications

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“…Jones and Hamilton have documented the ability of halide ions to control the conformation of hydrogen-bonded diphenylacetylenes. [243] In chloroform, the free diphenylacetylene derivative (Figure 97) exists mainly (ca. 9:1) in the conformation where the ester carbonyl group can hydrogen bond to one of the NÀH groups of the acidic urea functionality.…”

Section: Anion-responsive Complexes and Moleculesmentioning

confidence: 99%

Advances in Anion Supramolecular Chemistry: From Recognition to Chemical Applications

2014

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Since the start of this millennium, remarkable progress in the binding and sensing of anions has been taking place, driven in part by discoveries in the use of hydrogen bonding, as well as the previously under-exploited anion-π interactions and halogen bonding. However, anion supramolecular chemistry has developed substantially beyond anion recognition, and now encompasses a diverse range of disciplines. Dramatic advance has been made in the anion-templated synthesis of macrocycles and interlocked molecular architectures, while the study of transmembrane anion transporters has flourished from almost nothing into a rapidly maturing field of research. The supramolecular chemistry of anions has also found real practical use in a variety of applications such as catalysis, ion extraction, and the use of anions as stimuli for responsive chemical systems.

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Section: Anion-responsive Complexes and Moleculesmentioning

confidence: 99%

Advances in Anion Supramolecular Chemistry: From Recognition to Chemical Applications

2014

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“…As for the anion [47] and pH-dependent [32] switches described previously, the conformational bias can be determined by comparison of the 1 H-NMR spectrum of 3 with a set of control compounds. para-Substituted benzoic ester 5, which is incapable of intramolecular H-bonding, was synthesized via amide coupling of aniline 4 [31] with ferrocenoyl chloride (Scheme 2).…”

Section: Determining the Solution Phase Conformational Biasmentioning

confidence: 99%

Redox-Dependent Conformational Switching of Diphenylacetylenes

et al. 2014

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Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1 H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.

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“…[243] In Chloroform liegt das freie Diphenylacetylen hauptsächlich (ca. 9:1) in der Konformation vor, in der die Carbonylgruppe des Esters Wasserstoffbrücken zu einer der N-H-Gruppen der sauren Harnstoff-Funktion bilden kann.…”

Section: Anionen Als Template In Der Synthese Katalytischer Nanopartikelunclassified

“…Hamilton dokumentierte die Fähigkeit von Halogenidionen zur Kontrolle der Konformation von über Wasserstoffbrücken gebundenen Diphenylacetylenderivaten (Abbildung 97). [243] In Chloroform liegt das freie Diphenylacetylen hauptsächlich (ca. 9:1) in der Konformation vor, in der die Carbonylgruppe des Esters Wasserstoffbrücken zu einer der N-H-Gruppen der sauren Harnstoff-Funktion bilden kann.…”

Section: Auf Anionen Reagierende Komplexe Und Moleküleunclassified

Supramolekulare Chemie von Anionen: von der Erkennung zur chemischen Anwendung

Evans

Beer

2014

Angewandte Chemie

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Seit der Jahrtausendwende fanden bemerkenswerte Fortschritte bei der Bindung und dem Nachweis von Anionen statt, die teilweise von den Erkenntnissen zur Ausnutzung von Wasserstoffbrücken ebenso wie den zuvor selten eingesetzten Anionen‐π‐Wechselwirkungen und Halogenbrücken angetrieben wurden. Die supramolekulare Chemie von Anionen wurde indes substantiell über die Anionenerkennung hinaus weiterentwickelt und umfasst nun verschiedene Disziplinen. Große Fortschritte wurden bei der Synthese von Makrocyclen und ineinandergreifenden molekularen Architekturen mit Anionen als Templaten erzielt, während die Untersuchung von anionischen Transmembrantransportern aus dem Nichts heraus zu einem rasch wachsenden Forschungsgebiet erblühte. Die supramolekulare Chemie der Anionen kam außerdem in verschiedenen Anwendungsbereichen wie der Katalyse, der Ionenextraktion und der Verwendung von Anionen als Impuls für molekulare Systeme zum praktischen Einsatz.

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Anion‐Dependent Switching: Dynamically Controlling the Conformation of Hydrogen‐Bonded Diphenylacetylenes

Cited by 25 publications

References 41 publications

Advances in Anion Supramolecular Chemistry: From Recognition to Chemical Applications

Advances in Anion Supramolecular Chemistry: From Recognition to Chemical Applications

Redox-Dependent Conformational Switching of Diphenylacetylenes

Supramolekulare Chemie von Anionen: von der Erkennung zur chemischen Anwendung

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