The first quantitative detection of silver ion at micromolar levels in water using a redox-switchable ligand

Rojas, Maria T.; Medina, Julio C.; Gokel, George W.; Kaifer, Ángel E.

doi:10.1080/10610279308027500

Cited by 5 publications

(1 citation statement)

References 11 publications

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“…Loss of an electron affords the ferrocenium cation [Cp 2 Fe − e → Cp 2 Fe + ]. This type of switching has been used to advantage in ferrocenyl cryptands that selectively capture and release a variety of metals . It was thought that oxidation of the two ferrocene residues might permit the use of these compounds to function as anion binders, an application unrealized thus far in the present work.…”

Section: Resultsmentioning

confidence: 95%

Neutral Molecule Receptor Systems Using Ferrocene's “Atomic Ball Bearing” Character as the Flexible Element

Medina

Maguire

et al. 1997

J. Am. Chem. Soc.

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Fourteen novel ferrocene derivatives have been designed to serve as receptors for low molecular weight diamines. The compounds that have been prepared and fully characterized possess two ferrocenedicarboxylic acid residues bridged by amide formation in their respective 1‘-positions by 4,4‘-benzidinyl (15), 3,3‘-dimethoxy-4,4‘-benzidinyl (16), 2,7-fluorenyl (17), 3-methoxy-2,7-fluorenyl (18), 4-N-piperazinoanilinyl (19), N,N‘-4,4‘-bipiperdinyl (20), and 4,13-diaza-18-crown-6 (21). In two cases, ferrocenecarboxylic acid was bridged by spacers attached using 1-methylene groups. The bridges in these cases were 4,13-diaza-18-crown-6 (22) and 1,5-diaminoanthraquinone (24). In a single case, ferrocenecarboxylic acid was bridged by 1,5-dicarbonylnaphthalene (25). In one additional case, the bridge was created by formation of an imine followed by hydrogenation, but both compounds (26, 27) proved to be relatively unstable. Attempts to increase solubility afforded the N-ethylated derivative 28 of 15 and the derivative 29 of 27 having carboxamides in the 1‘-positions. A solid state structure of the diethyl ester of 20 confirms the design criteria. Complexation constants were determined in THF-d 8 or CDCl3 for combinations of receptors 18, 19, and 20 with 4-aminopyridine, N,N,N‘,N‘-tetramethylethylenediamine, N,N,N‘,N‘-tetramethylpropylenediamine, DABCO, 3-propyladenine, and benzimidazole and were in the range 102−104. The anticipated complexation mechanism for 20 with N,N,N‘,N‘-tetramethylpropylenediamine was confirmed by observation of an NOE between host and guest.

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Section: Resultsmentioning

confidence: 95%

Neutral Molecule Receptor Systems Using Ferrocene's “Atomic Ball Bearing” Character as the Flexible Element

Medina

Maguire

et al. 1997

J. Am. Chem. Soc.

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Redox-Switched Amphiphiles: Oxidized Ferrocene Derivatives Form Stable Vesicles When Either One or Two Alkyl Tails Are Present

Wang

Gokel

1997

J. Phys. Org. Chem.

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Thirty ferrocene derivatives were prepared and their ability to form vesicles in aqueous solution when oxidized was assessed. The compounds included alkyl ferrocenylmethyl ether derivatives of the form C 10 H 9 FeCH 2 OR in which R = octyl, dodecyl, tetradecyl, hexadecyl, octadecyl and eicosanyl. One single-tailed amine derivative, C 10 H 9 FeCH 2 NR 2 , R = octadecyl, was studied. Alkylferrocene derivatives had the form C 10 H 9 FeR in which R = butyl, decyl, tetradecyl, hexadecyl, octadecyl, eicosanyl and docosanyl. Sixteen symmetrical 1,1Ј-disubstituted ferrocenes were also studied. Three ethers were of the form C 10 H 8 Fe-1,1Ј-(CH 2 OR), 2 , R = tetradecyl, hexadecyl and octadecyl. Four corresponding dialkyl derivatives of the form C 10 H 8 Fe-1,1Ј-R 2 , R = decyl, tetradecyl, hexadecyl and octadecyl, were assessed. Finally, a range of 1,1Ј-disubstituted ferrocene derivatives were analyzed. These all had the form C 10 H 8 Fe-1,1Ј-(COR) 2 , for which R has the following identities: octyl, tridecyl, pentadecyl and heptadecyl (ketones); heptadecyloxy, 3-cholesteryl and 3-cholestanyl (esters); and two amides, R = NHC 18 H 37 and N(C 18 H 37 ) 2 . The alkyl and ether derivatives could be readily oxidized and formed vesicular aggregates upon sonication. The ketones, esters and amides could be oxidized but the ferricenium derivatives did not form stable aggregates. An interesting observation is that the aggregates formed were vesicular whether the ferrocene derivative had one or two alkyl tails.

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Supramolekulare Elektrochemie

1998

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Welche Möglichkeiten bietet die Elektrochemie der supramolekularen Chemie? Einerseits liefert sie Informationen, die mit spektroskopischen und massenspektrometrischen Methoden nicht zugänglich sind, andererseits lassen sich mit ihr supramolekulare Wechselwirkungen beeinflussen. Rechts ist exemplarisch das Cyclovoltammogramm des gezeigten Lanthan‐Kryptats abgebildet; nur die ersten drei Reduktionen werden registriert, obwohl insgesamt sechs Elektronen auf die Bipyridineinheiten übertragen werden können (E in V gegen Ferrocen/Ferrocenium).

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The first quantitative detection of silver ion at micromolar levels in water using a redox-switchable ligand

Cited by 5 publications

References 11 publications

Neutral Molecule Receptor Systems Using Ferrocene's “Atomic Ball Bearing” Character as the Flexible Element

Neutral Molecule Receptor Systems Using Ferrocene's “Atomic Ball Bearing” Character as the Flexible Element

Redox-Switched Amphiphiles: Oxidized Ferrocene Derivatives Form Stable Vesicles When Either One or Two Alkyl Tails Are Present

Supramolekulare Elektrochemie

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