New Polyamide Cryptand for Anion Binding

Kang, Sung Ok; Llinares, José M.; Powell, Douglas R.; VanderVelde, David; Bowman‐James, Kristin

doi:10.1021/ja034969+

Cited by 229 publications

(166 citation statements)

References 17 publications

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“…We have isolated and structurally characterized a number of fluoride complexes with both monocyclic and bicyclic amine-based [4] and amide-based [5] anion receptors. Despite finding bifluoride in the crystal lattice in a number of the amine-based macrocycles and cryptands, we had not encountered an encapsulated bifluoride.…”

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confidence: 99%

“…[9] Although the isolation of a bifluoride complex was not necessarily anticipated, fluoride is known to be a strong base in organic solvents; for example, it abstracts a b-hydrogen atom from anhydrous tetra-n-butylammonium salts to yield 1-butene, tri-n-butylamine, and tetra-n-butylammonium bifluoride. [10] Fluoride has also been observed to abstract hydrogen from amide-based macrocycles [11] and cryptands, [5] as well as urea-, [12] thiourea-, [13] and pyrrole-based [14] acyclic anion hosts, often with the observation of bifluoride in the 1 H NMR spectra. Even pure tetra-n-butylammonium fluoride contains small amounts of bifluoride.…”

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Trapped Bifluoride

et al. 2006

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The quest is over: A tricyclic amide‐based anion receptor has been synthesized by connecting two monocyclic precursors. The receptor is highly selective for the binding of the elusive bifluoride anion HF2−, and the adduct represents the first structural example of an encapsulated bifluoride. The bifluoride lies midway between the two macrocycles making up the tricycle and is held by four hydrogen‐bonding contacts with the macrocyclic amides.

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“…[41] In diesem Zusammenhang erwähnenswert ist die Arbeit von Bowman-James und Mitarbeitern; sie untersuchten neutrale Kryptanden (hergestellt durch Reaktion von Tri(2-aminoethyl)amin (kurz "Tren") mit Di(isophthaloylchloriden), die Fluorid mit K a > 10 5 m À1 in konkurrierendem [D 6 ]DMSO binden kçnnen (Abbildung 6 a). [42] Vor kurzem beschrieben Mani et al die Fähigkeit von Polypyrrol-Kryptanden, in [D 6 ]DMSO ebenfalls Fluorid zu binden (Abbildung 6 b). [43] Eine bemerkenswerte Errungenschaft auf diesem Gebiet ist die selektive Erkennung des radioaktiven Schadstoffs 99 TcO 4 À durch einen protonierten Kryptanden in saurem Wasser (Abbildung 6 c).…”

Section: Neue N-h- O-h-und C-h-haltige Rezeptorenunclassified

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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“…Some of them have a closed polycyclic structure that forms a cage. [13] In others, arms containing the interacting groups are appended to a defined platform. For instance, amide derivatives of the tripodal tetramine tren have been used as trifurcate anion receptors.…”

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confidence: 99%

What Anions Do Inside a Receptor's Cavity: A Trifurcate Anion Receptor Providing Both Electrostatic and Hydrogen‐Bonding Interactions

Amendola¹,

Boiocchi²,

Fabbrizzi³

et al. 2005

Chemistry A European J

111

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The trifurcate receptor 1(3+) forms stable 1:1 complexes with halide and oxo anions in MeCN solution, as shown by spectrophotometric and 1H NMR experiments, and selectively recognizes chloride (lg K(ass) > 7) in the presence of fluoride and bromide. The high stability reflects the receptor's ability to donate up to six hydrogen bonds (from three pyrrole N-H and three C-H fragments, polarized by the proximate positive charge) to the included anion. Addition of an excess of more basic anions (F- and CH3COO-) induces stepwise deprotonation of the N-H groups, an event signalled by the appearance of a bright yellow color. Crystal and molecular structures are reported for the complex with NO3(-) and a capsule consisting of two interconnected trifurcate subunits, one of which includes an H-bound Br- ion, while the other is doubly deprotonated and includes an H-bound water molecule. Finally, evidence is given for the formation in solution of an authentic complex of OH-, in which H-bound hydroxide is included within the cavity of 1(3+).

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New Polyamide Cryptand for Anion Binding

Cited by 229 publications

References 17 publications

Trapped Bifluoride

Trapped Bifluoride

Supramolekulare Chemie von Anionen: von der Erkennung zur chemischen Anwendung

What Anions Do Inside a Receptor's Cavity: A Trifurcate Anion Receptor Providing Both Electrostatic and Hydrogen‐Bonding Interactions

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