Ferrocenyl iron as a donor group for complexed silver in ferrocenyldimethyl[2.2]cryptand: a redox-switched receptor effective in water

Medina, Julio C.; Goodnow, Timothy T.; Rojas, Maria T.; Atwood, Jerry L.; Lynn, Bert C.; Kaifer, Ángel E.; Gokel, George W.

doi:10.1021/ja00052a064

Cited by 213 publications

(110 citation statements)

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“…29,30 These ligands were formed by a central skeleton of one or two metallocenes carrying a crown ether substructure on each cyclopentadienyl moiety. The resulting ligand structure is three-dimensional and can accommodate one29,30 or two30 metal cations inside its cavity (see Fig.…”

Section: Investigation Of Solution Equilibria : Fab and Electrospray mentioning

confidence: 99%

Special feature: Perspective. Host–guest chemistry in the mass spectrometer

Vincenti

1995

J. Mass Spectrom.

122

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The study of host-guest chemistry in the gas phase has been pursued systematically only in the last 5 years, after sporadic interest in the 1980s, despite extensive investigation of this chemistry in the condensed phase and the success encountered in several Ðelds of application. Most gas-phase studies have been performed under the controlled conditions that can be achieved inside a mass spectrometer, where solvent e †ects are not present. At this point, the Ðrst evaluation of the achievements and knowledge emerging from these mass spectrometric investigations can be attempted. At the same time, it is possible to evaluate the most promising subjects for future research. This review undertakes these tasks, by presenting (i) applications where mass spectrometry was used to investigate condensed phase equilibria and, more extensively, (ii) experiments where host-guest complexes were formed directly in the gas phase. The latter processes are discussed in detail in relation to the structural and electronic e †ects, the energetic requirements and the dependence on size, rigidity, spatial geometry and functional groups of both hosts and guests. All these e †ects combined are likely to contribute to the strength and multiplicity of the non-covalent bonds that allow the complex to be formed. The macro(poly)cyclic hosts considered include crown ethers, cryptands, cyclodextrins, calixarenes, cryptophanes, cavitands, carcerands and macrolides. The guests are either metal cations or organic molecules and ions.

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Section: Investigation Of Solution Equilibria : Fab and Electrospray mentioning

confidence: 99%

Special feature: Perspective. Host–guest chemistry in the mass spectrometer

Vincenti

1995

J. Mass Spectrom.

122

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“…[4] On the other hand, there are a few precedents for ironmetal-ion interactions in several complexes of transitionmetal ions in which a ferrocenyl group acts as a donor in the coordination sphere of the metal ion. [5] In this context, it has been reported that ferrocene behaves as a moderately strong base towards the Li + cation to form complexes.…”

Section: Introductionmentioning

confidence: 99%

Selective Metal‐Cation Recognition by [2.2]Ferrocenophanes: The Cases of Zinc‐ and Lithium‐Sensing

Otón

Ratera

Espinosa

et al. 2010

Chemistry A European J

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The synthesis, electrochemical, optical, and cation-sensing properties of [2.2]ferrocenophanes, in which the two ferrocene subunits are linked through two aldiminic or iminophosphorane moieties, are reported. The new compounds show remarkably selective cation-sensing properties due to the presence of redox-active units (ferrocene) and aza-unsaturated functionalities that are able to act as putative cation-binding sites. In this structural motif, the aldimine groups act as a highly selective binding site for Zn(2+) cations, whereas the iminophosphorane bridges display an unusually strong binding affinity towards Li(+) cations, which could be explained by an additional LiFe interaction. The X-ray structure of the complex 4Li(+) as well as detailed NMR spectroscopic studies, both in solution and in the solid state, support this assessment. Experimental data and conclusions about the cation-sensing capabilities of this family of compounds are supported by DFT calculations.

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“…However, quantitative accounts of these phenomena are rare in the literature, [6,[13][14][15][16][17][18][19][20][21] possibly due to the difficulty to experimentally probe individual molecules, and also to the belief that intramolecular electrostatic interactions are complicated (particularly in macromolecules) and that they hence deviate inevitably from Coulomb's law. Through a combined electrochemical and supramolecular approach, we demonstrate herein that Coulomb's law can be quantitatively followed in macromolecules.…”

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confidence: 99%

“…[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Generally, in these redox-active receptor molecules, the ion binding at the receptor site induces a potential shift, DE 1/2 , in the adjacent redox center. The electron transfer at the redox center also changes the complexation ability of the neighboring macrocycle.…”

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confidence: 99%