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In order to get more insights into the spin-density distribution of 1?+, the bis- and tetra-15N-labelled species 1a?+, 1b?+ and 1c?+ were synthesized and investigated by EPR and 15N as well as 14N ENDOR spectroscopy, revealing that the largest N hyperfine coupling constants are due to the nitrogen atoms of the central bridge. According to 1H ENDOR there seems to be a small coupling with the protons of both phenyl rings which cannot be resolved in the EPR spectrum.The electrochemical properties of the related mesoionic compounds 5-10 were also investigated in Py or DCM solutions. In the cathodic process, a reduction peak of 9 and 10 was observed due to their reversible one-electron reduction to the corresponding radical anions. The radical obtained on reduction of 10 was characterized by EPR spectroscopy. On the other hand, 5-8 can be reduced by a formal two-electron transfer up to the corresponding dianions which are re-oxidizable to the neutral state. 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Synthesis, electrochemical investigation and EPR spectroscopy of a reversible four-stage redox system based on mesoionic 5,5'-azinobis(1,3-diphenyltetrazole) and related mesoionic compounds
https://nitech.repo.nii.ac.jp/records/4613
https://nitech.repo.nii.ac.jp/records/4613148c55bc-4bd3-47bd-87ec-5a1f006aa3d4
名前 / ファイル | ライセンス | アクション |
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本文_fulltext (374.2 kB)
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J. Chem. Soc., Perkin Trans. 2, 1999, 985-995 -Reproduced by permission of The Royal Society of Chemistry (RSC)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2012-11-06 | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | Synthesis, electrochemical investigation and EPR spectroscopy of a reversible four-stage redox system based on mesoionic 5,5'-azinobis(1,3-diphenyltetrazole) and related mesoionic compounds | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Araki, Shuki
× Araki, Shuki× Yamamoto, Kaori× Inoue, Tomoko× Fujimoto, Koji× Yamamura, Hatsuo× Kawai, Masao× Butsugan, Yasuo× Zhou, Jinkui× Eichhorn, Emerich× Rieker, Anton× Huber, Martina |
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著者別名 | ||||||
姓名 | 荒木, 修喜 | |||||
著者別名 | ||||||
姓名 | 山村, 初雄 | |||||
書誌情報 |
Journal of the Chemical Society. Perkin transactions 2 巻 1999, 号 5, p. 985-995, 発行日 1999-01-01 |
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出版者 | ||||||
出版者 | Royal Society of Chemistry | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 03009580 | |||||
書誌レコードID(NCID) | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AA00695145 | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | http://dx.doi.org/10.1039/A809386E | |||||
関連名称 | 10.1039/A809386E | |||||
内容記述 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Mesoionic 5,5′-azinobis(1,3-diphenyltetrazole) 1 was prepared, and its chemical oxidation gave stable crystals of the corresponding radical cation 1?+ and dication 12+, which reversibly gave back azine 1 on reduction with zinc. Electrochemical investigations of 1 using cyclovoltammetry and differential pulse voltammetry in pyridine (Py) or dichloromethane (DCM) also revealed the two reversible successive one-electron oxidations leading to dication 12+via radical cation 1?+, both of which can be reduced to the neutral state 1. In the cathodic process, 1 was reduced by two consecutive one-electron transfers at only slightly different potentials up to the corresponding dianion 12? which could be re-oxidized to the neutral state; thus constituting a reversible four-stage redox system. Radical cation 1?+ and anion 1?- were characterized by EPR spectroscopy. In order to get more insights into the spin-density distribution of 1?+, the bis- and tetra-15N-labelled species 1a?+, 1b?+ and 1c?+ were synthesized and investigated by EPR and 15N as well as 14N ENDOR spectroscopy, revealing that the largest N hyperfine coupling constants are due to the nitrogen atoms of the central bridge. According to 1H ENDOR there seems to be a small coupling with the protons of both phenyl rings which cannot be resolved in the EPR spectrum.The electrochemical properties of the related mesoionic compounds 5-10 were also investigated in Py or DCM solutions. In the cathodic process, a reduction peak of 9 and 10 was observed due to their reversible one-electron reduction to the corresponding radical anions. The radical obtained on reduction of 10 was characterized by EPR spectroscopy. On the other hand, 5-8 can be reduced by a formal two-electron transfer up to the corresponding dianions which are re-oxidizable to the neutral state. In the anodic process, 9/10 undergo irreversible one-electron oxidations whereas 5/6 (in DCM) and 7/8 (in Py) experience reversible or irreversible step by step two-electron oxidations leading to the dications. In Py the oxidation products of 5/6 react to further species revealing two more oxidation and several rereduction peaks. On the other hand, the oxidation products of 7/8 are instable in DCM (one main oxidation and rereduction peak). The electrochemical data are discussed in terms of delocalization in the cations and conjugation in the dications. | |||||
フォーマット | ||||||
内容記述タイプ | Other | |||||
内容記述 | application/pdf |