Polysubstituted ferrocenes as tunable redox mediators
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Sven D Waniek
- Jan Klett
- Christoph Foerster
- Katja Heinze
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000431950200001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.3762/bjoc.14.86
- Externe Identifier
- Clarivate Analytics Document Solution ID: GF4RF
- PubMed Identifier: 29977372
- ISSN
- 1860-5397
- Zeitschrift
- BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
- Schlüsselwörter
- cyclic voltammetry
- ferrocene
- paramagnetic NMR spectroscopy
- redox mediator
- spectroelectrochemistry
- Paginierung
- 1004 - 1015
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Titel
- Polysubstituted ferrocenes as tunable redox mediators
- Sub types
- Article
- Ausgabe der Zeitschrift
- 14
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Abstract
- <jats:p>A series of four ferrocenyl ester compounds, 1-methoxycarbonyl- (<jats:bold>1</jats:bold>), 1,1’-bis(methoxycarbonyl)- (<jats:bold>2</jats:bold>), 1,1’,3-tris(methoxycarbonyl)- (<jats:bold>3</jats:bold>) and 1,1’,3,3’-tetrakis(methoxycarbonyl)ferrocene (<jats:bold>4</jats:bold>), has been studied with respect to their potential use as redox mediators. The impact of the number and position of ester groups present in <jats:bold>1</jats:bold>–<jats:bold>4</jats:bold> on the electrochemical potential <jats:italic>E</jats:italic><jats:sub>1/2</jats:sub> is correlated with the sum of Hammett constants. The <jats:bold>1</jats:bold>/<jats:bold>1</jats:bold><jats:bold><jats:sup>+</jats:sup></jats:bold>–<jats:bold>4</jats:bold>/<jats:bold>4</jats:bold><jats:bold><jats:sup>+</jats:sup></jats:bold> redox couples are chemically stable under the conditions of electrolysis as demonstrated by IR and UV–vis spectroelectrochemical methods. The energies of the C=O stretching vibrations of the ester moieties and the energies of the UV–vis absorptions of <jats:bold>1</jats:bold>–<jats:bold>4</jats:bold> and <jats:bold>1</jats:bold><jats:bold><jats:sup>+</jats:sup></jats:bold>–<jats:bold>4</jats:bold><jats:bold><jats:sup>+</jats:sup></jats:bold> correlate with the number of ester groups. Paramagnetic <jats:sup>1</jats:sup>H NMR redox titration experiments give access to the chemical shifts of <jats:bold>1</jats:bold><jats:bold><jats:sup>+</jats:sup></jats:bold>–<jats:bold>4</jats:bold><jats:bold><jats:sup>+</jats:sup></jats:bold> and underline the fast electron self-exchange of the ferrocene/ferrocenium redox couples, required for rapid redox mediation in organic electrosynthesis.</jats:p>
- Date of acceptance
- 2018
- Autoren
- Sven D Waniek
- Jan Klett
- Christoph Förster
- Katja Heinze
- DOI
- 10.3762/bjoc.14.86
- eISSN
- 1860-5397
- Zeitschrift
- Beilstein Journal of Organic Chemistry
- Sprache
- en
- Online publication date
- 2018
- Paginierung
- 1004 - 1015
- Status
- Published online
- Herausgeber
- Beilstein Institut
- Herausgeber URL
- http://dx.doi.org/10.3762/bjoc.14.86
- Datum der Datenerfassung
- 2021
- Titel
- Polysubstituted ferrocenes as tunable redox mediators
- Ausgabe der Zeitschrift
- 14
Datenquelle: Crossref
- Abstract
- A series of four ferrocenyl ester compounds, 1-methoxycarbonyl- (<b>1</b>), 1,1'-bis(methoxycarbonyl)- (<b>2</b>), 1,1',3-tris(methoxycarbonyl)- (<b>3</b>) and 1,1',3,3'-tetrakis(methoxycarbonyl)ferrocene (<b>4</b>), has been studied with respect to their potential use as redox mediators. The impact of the number and position of ester groups present in <b>1</b>-<b>4</b> on the electrochemical potential <i>E</i><sub>1/2</sub> is correlated with the sum of Hammett constants. The <b>1</b>/<b>1</b><b><sup>+</sup></b> -<b>4</b>/<b>4</b><b><sup>+</sup></b> redox couples are chemically stable under the conditions of electrolysis as demonstrated by IR and UV-vis spectroelectrochemical methods. The energies of the C=O stretching vibrations of the ester moieties and the energies of the UV-vis absorptions of <b>1</b>-<b>4</b> and <b>1</b><b><sup>+</sup></b> -<b>4</b><b><sup>+</sup></b> correlate with the number of ester groups. Paramagnetic <sup>1</sup>H NMR redox titration experiments give access to the chemical shifts of <b>1</b><b><sup>+</sup></b> -<b>4</b><b><sup>+</sup></b> and underline the fast electron self-exchange of the ferrocene/ferrocenium redox couples, required for rapid redox mediation in organic electrosynthesis.
- Addresses
- Institute of Inorganic Chemistry and Analytical Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany.
- Autoren
- Sven D Waniek
- Jan Klett
- Christoph Förster
- Katja Heinze
- DOI
- 10.3762/bjoc.14.86
- eISSN
- 1860-5397
- Externe Identifier
- PubMed Identifier: 29977372
- PubMed Central ID: PMC6009500
- Open access
- true
- ISSN
- 1860-5397
- Zeitschrift
- Beilstein journal of organic chemistry
- Sprache
- eng
- Medium
- Electronic-eCollection
- Online publication date
- 2018
- Open access status
- Open Access
- Paginierung
- 1004 - 1015
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Publisher licence
- CC BY
- Datum der Datenerfassung
- 2018
- Titel
- Polysubstituted ferrocenes as tunable redox mediators.
- Sub types
- research-article
- Journal Article
- Ausgabe der Zeitschrift
- 14
Files
https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-14-86.pdf https://europepmc.org/articles/PMC6009500?pdf=render
Datenquelle: Europe PubMed Central
- Abstract
- A series of four ferrocenyl ester compounds, 1-methoxycarbonyl- (1), 1,1'-bis(methoxycarbonyl)- (2), 1,1',3-tris(methoxycarbonyl)- (3) and 1,1',3,3'-tetrakis(methoxycarbonyl)ferrocene (4), has been studied with respect to their potential use as redox mediators. The impact of the number and position of ester groups present in 1-4 on the electrochemical potential E1/2 is correlated with the sum of Hammett constants. The 1/1+ -4/4+ redox couples are chemically stable under the conditions of electrolysis as demonstrated by IR and UV-vis spectroelectrochemical methods. The energies of the C=O stretching vibrations of the ester moieties and the energies of the UV-vis absorptions of 1-4 and 1+ -4+ correlate with the number of ester groups. Paramagnetic 1H NMR redox titration experiments give access to the chemical shifts of 1+ -4+ and underline the fast electron self-exchange of the ferrocene/ferrocenium redox couples, required for rapid redox mediation in organic electrosynthesis.
- Date of acceptance
- 2018
- Autoren
- Sven D Waniek
- Jan Klett
- Christoph Förster
- Katja Heinze
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/29977372
- DOI
- 10.3762/bjoc.14.86
- Externe Identifier
- PubMed Central ID: PMC6009500
- ISSN
- 1860-5397
- Zeitschrift
- Beilstein J Org Chem
- Schlüsselwörter
- cyclic voltammetry
- ferrocene
- paramagnetic NMR spectroscopy
- redox mediator
- spectroelectrochemistry
- Sprache
- eng
- Country
- Germany
- Paginierung
- 1004 - 1015
- Datum der Veröffentlichung
- 2018
- Status
- Published online
- Titel
- Polysubstituted ferrocenes as tunable redox mediators.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 14
Datenquelle: PubMed
- Beziehungen:
-