Dicationic Acridinium/Carbene Hybrids as Strongly Oxidizing Photocatalysts
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Samaresh C Sau
- Matthias Schmitz
- Chris Burdenski
- Marcel Baumert
- Patrick W Antoni
- Christoph Kerzig
- Max M Hansmann
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:001158839100001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/jacs.3c12766
- eISSN
- 1520-5126
- Externe Identifier
- Clarivate Analytics Document Solution ID: HI3Z0
- PubMed Identifier: 38266168
- ISSN
- 0002-7863
- Ausgabe der Veröffentlichung
- 5
- Zeitschrift
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Paginierung
- 3416 - 3426
- Datum der Veröffentlichung
- 2024
- Status
- Published
- Titel
- Dicationic Acridinium/Carbene Hybrids as Strongly Oxidizing Photocatalysts
- Sub types
- Article
- Ausgabe der Zeitschrift
- 146
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Samaresh C Sau
- Matthias Schmitz
- Chris Burdenski
- Marcel Baumert
- Patrick W Antoni
- Christoph Kerzig
- Max M Hansmann
- DOI
- 10.1021/jacs.3c12766
- eISSN
- 1520-5126
- ISSN
- 0002-7863
- Ausgabe der Veröffentlichung
- 5
- Zeitschrift
- Journal of the American Chemical Society
- Sprache
- en
- Online publication date
- 2024
- Paginierung
- 3416 - 3426
- Datum der Veröffentlichung
- 2024
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/jacs.3c12766
- Datum der Datenerfassung
- 2024
- Titel
- Dicationic Acridinium/Carbene Hybrids as Strongly Oxidizing Photocatalysts
- Ausgabe der Zeitschrift
- 146
Datenquelle: Crossref
- Abstract
- A new design concept for organic, strongly oxidizing photocatalysts is described based upon dicationic acridinium/carbene hybrids. A highly modular synthesis of such hybrids is presented, and the dications are utilized as novel, tailor-made photoredox catalysts in the direct oxidative C-N coupling. Under optimized conditions, benzene and even electron-deficient arenes can be oxidized and coupled with a range of <i>N</i>-heterocycles in high to excellent yields with a single low-energy photon per catalytic turnover, while commonly used acridinium photocatalysts are not able to perform the challenging oxidation step. In contrast to traditional photocatalysts, the hybrid photocatalysts reported here feature a reversible two-electron redox system with regular or inverted redox potentials for the two-electron transfer. The different oxidation states could be isolated and structurally characterized supported by NMR, EPR, and X-ray analysis. Mechanistic experiments employing time-resolved emission and transient absorption spectroscopy unambiguously reveal the outstanding excited-state potential of our best-performing catalyst (+2.5 V vs SCE), and they provide evidence for mechanistic key steps and intermediates.
- Addresses
- Fakultät für Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Str. 6, Dortmund 44227, Germany.
- Autoren
- Samaresh C Sau
- Matthias Schmitz
- Chris Burdenski
- Marcel Baumert
- Patrick W Antoni
- Christoph Kerzig
- Max M Hansmann
- DOI
- 10.1021/jacs.3c12766
- eISSN
- 1520-5126
- Externe Identifier
- PubMed Identifier: 38266168
- Funding acknowledgements
- Fonds der Chemischen Industrie:
- Deutsche Forschungsgemeinschaft: HA 8832/1-1
- Open access
- false
- ISSN
- 0002-7863
- Zeitschrift
- Journal of the American Chemical Society
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2024
- Datum der Veröffentlichung
- 2024
- Status
- Published
- Datum der Datenerfassung
- 2024
- Titel
- Dicationic Acridinium/Carbene Hybrids as Strongly Oxidizing Photocatalysts.
- Sub types
- Journal Article
Datenquelle: Europe PubMed Central
- Abstract
- A new design concept for organic, strongly oxidizing photocatalysts is described based upon dicationic acridinium/carbene hybrids. A highly modular synthesis of such hybrids is presented, and the dications are utilized as novel, tailor-made photoredox catalysts in the direct oxidative C-N coupling. Under optimized conditions, benzene and even electron-deficient arenes can be oxidized and coupled with a range of N-heterocycles in high to excellent yields with a single low-energy photon per catalytic turnover, while commonly used acridinium photocatalysts are not able to perform the challenging oxidation step. In contrast to traditional photocatalysts, the hybrid photocatalysts reported here feature a reversible two-electron redox system with regular or inverted redox potentials for the two-electron transfer. The different oxidation states could be isolated and structurally characterized supported by NMR, EPR, and X-ray analysis. Mechanistic experiments employing time-resolved emission and transient absorption spectroscopy unambiguously reveal the outstanding excited-state potential of our best-performing catalyst (+2.5 V vs SCE), and they provide evidence for mechanistic key steps and intermediates.
- Autoren
- Samaresh C Sau
- Matthias Schmitz
- Chris Burdenski
- Marcel Baumert
- Patrick W Antoni
- Christoph Kerzig
- Max M Hansmann
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/38266168
- DOI
- 10.1021/jacs.3c12766
- eISSN
- 1520-5126
- Ausgabe der Veröffentlichung
- 5
- Zeitschrift
- J Am Chem Soc
- Sprache
- eng
- Country
- United States
- Paginierung
- 3416 - 3426
- Datum der Veröffentlichung
- 2024
- Status
- Published
- Titel
- Dicationic Acridinium/Carbene Hybrids as Strongly Oxidizing Photocatalysts.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 146
Datenquelle: PubMed
- Beziehungen:
- Eigentum von