Laser-Induced Wurtz-Type Syntheses with a Metal-Free Photoredox Catalytic Source of Hydrated Electrons
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Tim Kohlmann
- Christoph Kerzig
- Martin Goez
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000476918500027&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1002/chem.201901618
- eISSN
- 1521-3765
- Externe Identifier
- Clarivate Analytics Document Solution ID: IK9MF
- PubMed Identifier: 31059596
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 42
- Zeitschrift
- CHEMISTRY-A EUROPEAN JOURNAL
- Schlüsselwörter
- hydrated electrons
- laser chemistry
- photocatalysis
- radical reactions
- sustainable chemistry
- Paginierung
- 9991 - 9996
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Titel
- Laser-Induced Wurtz-Type Syntheses with a Metal-Free Photoredox Catalytic Source of Hydrated Electrons
- Sub types
- Article
- Ausgabe der Zeitschrift
- 25
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Abstract
- <jats:title>Abstract</jats:title><jats:p>Upon irradiation with ns laser pulses at 355 nm, 2‐aminoanthracene in SDS micelles readily produces hydrated electrons. These “super‐reductants” rapidly attack substrates such as chloro‐organics and convert them into carbon‐centred radicals through dissociative electron transfer. For a catalytic cycle, the aminoanthracene needs to be restored from its photoionization by‐product, the radical cation, by a sacrificial donor. The ascorbate monoanion can only achieve this across the micelle–water interface, but the monoanion of ascorbyl palmitate results in a fully micelle‐contained regenerative electron source. The shielding by the micelle in the latter case not only increases the life of the catalyst but also strongly suppresses the interception of the carbon‐centred radicals by the hydrogen‐donating ascorbate moiety; and in conjunction with the high local concentrations effected by the pulsed laser, termination by radical dimerization thus dominates. We have obtained a complete and consistent picture through monitoring the individual steps and the assembled system by flash photolysis on fast and slow timescales, from microseconds to minutes; and in preparative studies on a variety of substrates, we have achieved up to quantitative dimerization with a turnover on the order of 1 mmol per hour.</jats:p>
- Autoren
- Tim Kohlmann
- Christoph Kerzig
- Martin Goez
- DOI
- 10.1002/chem.201901618
- eISSN
- 1521-3765
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 42
- Zeitschrift
- Chemistry – A European Journal
- Sprache
- en
- Online publication date
- 2019
- Paginierung
- 9991 - 9996
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Herausgeber
- Wiley
- Herausgeber URL
- http://dx.doi.org/10.1002/chem.201901618
- Datum der Datenerfassung
- 2023
- Titel
- Laser‐Induced Wurtz‐Type Syntheses with a Metal‐Free Photoredox Catalytic Source of Hydrated Electrons
- Ausgabe der Zeitschrift
- 25
Data source: Crossref
- Abstract
- Upon irradiation with ns laser pulses at 355 nm, 2-aminoanthracene in SDS micelles readily produces hydrated electrons. These "super-reductants" rapidly attack substrates such as chloro-organics and convert them into carbon-centred radicals through dissociative electron transfer. For a catalytic cycle, the aminoanthracene needs to be restored from its photoionization by-product, the radical cation, by a sacrificial donor. The ascorbate monoanion can only achieve this across the micelle-water interface, but the monoanion of ascorbyl palmitate results in a fully micelle-contained regenerative electron source. The shielding by the micelle in the latter case not only increases the life of the catalyst but also strongly suppresses the interception of the carbon-centred radicals by the hydrogen-donating ascorbate moiety; and in conjunction with the high local concentrations effected by the pulsed laser, termination by radical dimerization thus dominates. We have obtained a complete and consistent picture through monitoring the individual steps and the assembled system by flash photolysis on fast and slow timescales, from microseconds to minutes; and in preparative studies on a variety of substrates, we have achieved up to quantitative dimerization with a turnover on the order of 1 mmol per hour.
- Addresses
- Martin-Luther-Universität Halle-Wittenberg, Institut für Chemie, Kurt-Mothes-Str. 2, 06120, Halle (Saale), Germany.
- Autoren
- Tim Kohlmann
- Christoph Kerzig
- Martin Goez
- DOI
- 10.1002/chem.201901618
- eISSN
- 1521-3765
- Externe Identifier
- PubMed Identifier: 31059596
- Open access
- false
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 42
- Zeitschrift
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2019
- Paginierung
- 9991 - 9996
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Datum der Datenerfassung
- 2019
- Titel
- Laser-Induced Wurtz-Type Syntheses with a Metal-Free Photoredox Catalytic Source of Hydrated Electrons.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 25
Data source: Europe PubMed Central
- Abstract
- Upon irradiation with ns laser pulses at 355 nm, 2-aminoanthracene in SDS micelles readily produces hydrated electrons. These "super-reductants" rapidly attack substrates such as chloro-organics and convert them into carbon-centred radicals through dissociative electron transfer. For a catalytic cycle, the aminoanthracene needs to be restored from its photoionization by-product, the radical cation, by a sacrificial donor. The ascorbate monoanion can only achieve this across the micelle-water interface, but the monoanion of ascorbyl palmitate results in a fully micelle-contained regenerative electron source. The shielding by the micelle in the latter case not only increases the life of the catalyst but also strongly suppresses the interception of the carbon-centred radicals by the hydrogen-donating ascorbate moiety; and in conjunction with the high local concentrations effected by the pulsed laser, termination by radical dimerization thus dominates. We have obtained a complete and consistent picture through monitoring the individual steps and the assembled system by flash photolysis on fast and slow timescales, from microseconds to minutes; and in preparative studies on a variety of substrates, we have achieved up to quantitative dimerization with a turnover on the order of 1 mmol per hour.
- Autoren
- Tim Kohlmann
- Christoph Kerzig
- Martin Goez
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/31059596
- DOI
- 10.1002/chem.201901618
- eISSN
- 1521-3765
- Ausgabe der Veröffentlichung
- 42
- Zeitschrift
- Chemistry
- Schlüsselwörter
- hydrated electrons
- laser chemistry
- photocatalysis
- radical reactions
- sustainable chemistry
- Sprache
- eng
- Country
- Germany
- Paginierung
- 9991 - 9996
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Titel
- Laser-Induced Wurtz-Type Syntheses with a Metal-Free Photoredox Catalytic Source of Hydrated Electrons.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 25
Data source: PubMed
- Beziehungen:
- Property of