Multisite Inclusion Complexation of Redox Active Dendrimer Guests

Castro, René; Cuadrado, Isabel; Alonso, Beatriz; Casado, Carmen M.; Morán, Moisés; Kaifer, Ángel E.

doi:10.1021/ja970922a

Cited by 170 publications

(130 citation statements)

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“…15 The 1:1 complexation of compound I (MW 273 Da) with b-or DM--CD (MW 1331 u) in the solution phase was reported to be specific. 12 For example, proton NMR experiments revealed a binding constant of 1230 M À1 for the inclusion complex of I with b-CD. 12 Likewise, the mass spectrum of an equimolar mixture of b-or DM-b-CD with I exhibited signals corresponding to a putative 1:1 inclusion complex, whose identity was examined by CID experiments.…”

Section: Resultsmentioning

confidence: 99%

“…12 For example, proton NMR experiments revealed a binding constant of 1230 M À1 for the inclusion complex of I with b-CD. 12 Likewise, the mass spectrum of an equimolar mixture of b-or DM-b-CD with I exhibited signals corresponding to a putative 1:1 inclusion complex, whose identity was examined by CID experiments. For instance, CID (collision energy = 28 eV) of m/z 1425 yielded the loss of the b-CD moiety as the predominant dissociation pathway (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…All the ferrocene derivatives were prepared according to the method reported previously, 12 and characterized by proton NMR, elemental analysis and mass spectrometry. All other chemicals were commercially available.…”

Section: An Api IIImentioning

confidence: 99%

“…11 Recently, Kaifer and co-workers reported evidence in support of inclusion complexation between b-CD and dimethyl-b-CD (DM-b-CD) and a series of redox active dendrimer guests bearing ferrocene moieties. 12 Multimetallic dendrimers with electron mobility capability may provide interesting electrical, optical and magnetic properties. Thus, it was intriguing to extend these abovementioned aqueous molecular recognition studies to the gas phase, to compare and to better understand the role of water and its effect on the importance of noncovalent interactions which control the host-guest processes.…”

mentioning

confidence: 99%

“…Future studies could involve studies on noncovalent complexation between multisite ferrocene containing dendrimers 12 with CDs in the gas phase.…”

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confidence: 99%

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Mass spectrometry studies on the complexation of several organometallic complexes by α- and β-cyclodextrins

Bakhtiar

Kaifer

1998

Rapid Commun. Mass Spectrom.

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The complexation of ferrocene and several ferrocene derivatives with the hosts a-cyclodextrin (a-CD) and b-cyclodextrin (b-CD) was investigated by electrospray mass spectrometry. A 2:1 complex was detected between a-CD and ferrocene while a 1:1 complex was observed with b-CD and this organometallic guest. All the remaining ferrocene derivatives surveyed in this work exhibited mass spectrometry signals corresponding to 1:1 complexes with either host. In contrast to previous electrochemical and proton NMR spectroscopic studies, no evidence was found for ternary or quaternary complexes in these host-guest systems. These results demonstrate for the first time that complexes between cyclodextrins and organometallic compounds are detected in the gas phase. # 1998 John Wiley & Sons, Ltd. Received 8 December 1997; Accepted 9 December 1997Rapid Commun. Mass Spectrom. 12, 111-114 (1998) Enzymes such as cyclodextrin-glycosyltransferases produce the cyclic dextrins, which are referred to as Schardinger dextrins or cyclodextrins (CDs). By virtue of steric reasons, CDs are formed in only three significant forms as a-, b-and g-cyclodextrins. CDs have the ability to selectively include a range of guest species in their hydrophobic cavities. The formation of an inclusion complex potentially alters the physical and chemical properties of the guest molecule. The binding forces associated with the CD-guest inclusion formation are attributed to a number of factors such as hydrophobic forces, hydrogen binding, size of the cavity, shape of the guest molecule and electrostatic interactions.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: An Api IIImentioning

confidence: 99%

mentioning

confidence: 99%

“…Future studies could involve studies on noncovalent complexation between multisite ferrocene containing dendrimers 12 with CDs in the gas phase.…”

mentioning

confidence: 99%

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Mass spectrometry studies on the complexation of several organometallic complexes by α- and β-cyclodextrins

Bakhtiar

Kaifer

1998

Rapid Commun. Mass Spectrom.

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Cyclic siloxanes and silsesquioxanes as cores and frameworks for the construction of ferrocenyl dendrimers and polymers

Casado

Cuadrado

Morán

et al. 1999

Appl. Organometal. Chem.

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Starting from 1,3,5,7‐tetramethylcyclotetrasiloxane as core, novel ferrocenyl silicon‐containing dendrimers have been constructed up to the third generation, which contains 16 peripheral ferrocene moieties. As precursors of these ferrocenyl dendritic molecules, SiCl‐ and Siallyl‐terminated cyclotetrasiloxane‐based dendrimers were also built step by step, by the repetition of hydrosilylation and alkenylation reactions as growing steps. The dendritic structures have been confirmed by 1H, 13C and 29Si NMR, infrared spectroscopy, elemental analysis, mass spectrometry and vapor‐pressure osmometry. Solution electrochemical studies showed that all the ferrocenyl redox centers attached to the dendritic surface behave as independent, electronically isolated units, so that the dendrimers exchange all the electrons simultaneously at the same potential. We also describe the application of the first redox‐active ferrocenyl polymer containing an octakis(dimethylsiloxy)octasilsesquioxane framework, as a mediator in the electrocatalytic oxidation of ascorbic acid. Copyright © 1999 John Wiley & Sons, Ltd.

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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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Multisite Inclusion Complexation of Redox Active Dendrimer Guests

Cited by 170 publications

References 18 publications

Mass spectrometry studies on the complexation of several organometallic complexes by α- and β-cyclodextrins

Mass spectrometry studies on the complexation of several organometallic complexes by α- and β-cyclodextrins

Cyclic siloxanes and silsesquioxanes as cores and frameworks for the construction of ferrocenyl dendrimers and polymers

Supramolekulare Elektrochemie

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