Host–Guest-Induced Electron Transfer Triggers Radical-Cation Catalysis
Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone “co-factors” by a simple Pd2L4 capsule promotes a range of bulk-phase, radical-cation cycloadditio...
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| Published in | Journal of the American Chemical Society Vol. 142; no. 5; pp. 2134 - 2139 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
05.02.2020
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone “co-factors” by a simple Pd2L4 capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host–guest-induced release of an “electron hole” will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species. |
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| AbstractList | Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone "co-factors" by a simple Pd2L4 capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host-guest-induced release of an "electron hole" will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species.Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone "co-factors" by a simple Pd2L4 capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host-guest-induced release of an "electron hole" will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species. Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone “co-factors” by a simple Pd2L4 capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host–guest-induced release of an “electron hole” will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species. Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone "co-factors" by a simple Pd L capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host-guest-induced release of an "electron hole" will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species. Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone “co-factors” by a simple Pd₂L₄ capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host–guest-induced release of an “electron hole” will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species. |
| Author | Stergiou, Athanasios D Young, Tom A Lusby, Paul J Symes, Mark D Spicer, Rebecca L Duarte, Fernanda |
| AuthorAffiliation | Chemistry Research Laboratory EaStCHEM School of Chemistry WestCHEM, School of Chemistry |
| AuthorAffiliation_xml | – name: Chemistry Research Laboratory – name: WestCHEM, School of Chemistry – name: EaStCHEM School of Chemistry |
| Author_xml | – sequence: 1 givenname: Rebecca L surname: Spicer fullname: Spicer, Rebecca L organization: EaStCHEM School of Chemistry – sequence: 2 givenname: Athanasios D surname: Stergiou fullname: Stergiou, Athanasios D organization: WestCHEM, School of Chemistry – sequence: 3 givenname: Tom A orcidid: 0000-0002-8432-7769 surname: Young fullname: Young, Tom A organization: Chemistry Research Laboratory – sequence: 4 givenname: Fernanda orcidid: 0000-0002-6062-8209 surname: Duarte fullname: Duarte, Fernanda email: fernanda.duartegonzalez@chem.ox.ac.uk organization: Chemistry Research Laboratory – sequence: 5 givenname: Mark D orcidid: 0000-0001-8067-5240 surname: Symes fullname: Symes, Mark D email: mark.symes@glasgow.ac.uk organization: WestCHEM, School of Chemistry – sequence: 6 givenname: Paul J orcidid: 0000-0001-8418-5687 surname: Lusby fullname: Lusby, Paul J email: paul.lusby@ed.ac.uk organization: EaStCHEM School of Chemistry |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31935091$$D View this record in MEDLINE/PubMed |
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| Snippet | Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein... |
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| SubjectTerms | catalytic activity Chemistry Chemistry, Multidisciplinary cycloaddition reactions electron transfer encapsulation oxidants Physical Sciences protonation quinones redox potential Science & Technology stoichiometry voltammetry |
| Title | Host–Guest-Induced Electron Transfer Triggers Radical-Cation Catalysis |
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