Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis
The photophysical properties and photocatalysis of tris(pentafluorophenyl)borane [B(C6F5)3], known as a strong Lewis acid, were revealed. The excited-state B(C6F5)3 exerts single-electron oxidation capability with an oxidation potential (Ered* = 2.02 V vs SCE) close to those of electronically unbias...
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| Format: | Article |
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Elsevier
2023-12-01
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| Series: | Journal of Photochemistry and Photobiology |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666469023000477 |
| _version_ | 1797405367441817600 |
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| author | Yoshitaka Aramaki Yuki Uchida Ryo Ishikawa Takashi Ooi |
| author_facet | Yoshitaka Aramaki Yuki Uchida Ryo Ishikawa Takashi Ooi |
| author_sort | Yoshitaka Aramaki |
| collection | DOAJ |
| description | The photophysical properties and photocatalysis of tris(pentafluorophenyl)borane [B(C6F5)3], known as a strong Lewis acid, were revealed. The excited-state B(C6F5)3 exerts single-electron oxidation capability with an oxidation potential (Ered* = 2.02 V vs SCE) close to those of electronically unbiased toluene derivatives (Eox = 2.01 to 2.29 V). This property was experimentally proven by the direct observation of the radical cation of the toluene dimer by the transient absorption spectroscopy of a mixture of B(C6F5)3 and toluene. In cooperation with a suitable Brønsted base catalyst, B(C6F5)3 catalytically generated benzylic radicals from toluene derivatives under photoirradiation for subsequent carbon-carbon bond-forming reactions. |
| first_indexed | 2024-03-09T03:09:00Z |
| format | Article |
| id | doaj.art-603f3b90729b4d9281a4f286eef7a42c |
| institution | Directory Open Access Journal |
| issn | 2666-4690 |
| language | English |
| last_indexed | 2024-03-09T03:09:00Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Photochemistry and Photobiology |
| spelling | doaj.art-603f3b90729b4d9281a4f286eef7a42c2023-12-04T05:24:13ZengElsevierJournal of Photochemistry and Photobiology2666-46902023-12-0118100206Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysisYoshitaka Aramaki0Yuki Uchida1Ryo Ishikawa2Takashi Ooi3Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, JapanInstitute of Transformative Bio-Molecules (WPI-ITbM) and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, JapanInstitute of Transformative Bio-Molecules (WPI-ITbM) and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, JapanCorresponding author.; Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, JapanThe photophysical properties and photocatalysis of tris(pentafluorophenyl)borane [B(C6F5)3], known as a strong Lewis acid, were revealed. The excited-state B(C6F5)3 exerts single-electron oxidation capability with an oxidation potential (Ered* = 2.02 V vs SCE) close to those of electronically unbiased toluene derivatives (Eox = 2.01 to 2.29 V). This property was experimentally proven by the direct observation of the radical cation of the toluene dimer by the transient absorption spectroscopy of a mixture of B(C6F5)3 and toluene. In cooperation with a suitable Brønsted base catalyst, B(C6F5)3 catalytically generated benzylic radicals from toluene derivatives under photoirradiation for subsequent carbon-carbon bond-forming reactions.http://www.sciencedirect.com/science/article/pii/S2666469023000477PhotooxidantBoraneRadical cationTransient absorption spectroscopyCarbon-carbon bond formation |
| spellingShingle | Yoshitaka Aramaki Yuki Uchida Ryo Ishikawa Takashi Ooi Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis Journal of Photochemistry and Photobiology Photooxidant Borane Radical cation Transient absorption spectroscopy Carbon-carbon bond formation |
| title | Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis |
| title_full | Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis |
| title_fullStr | Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis |
| title_full_unstemmed | Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis |
| title_short | Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis |
| title_sort | excited state tris pentafluorophenyl borane as a strong single electron oxidant photophysical properties and catalysis |
| topic | Photooxidant Borane Radical cation Transient absorption spectroscopy Carbon-carbon bond formation |
| url | http://www.sciencedirect.com/science/article/pii/S2666469023000477 |
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