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Site‐Selective N‐Methylation of 5,15‐Diazaporphyrins: Reactive Cationic Porphyrinoids that Provide Isoporphyrin Analogues
http://hdl.handle.net/2237/00032315
http://hdl.handle.net/2237/00032315f3e80685-d96f-4a5a-891c-1eed5de1ccb4
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
manuscript (2.4 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2020-06-09 | |||||
| タイトル | ||||||
| タイトル | Site‐Selective N‐Methylation of 5,15‐Diazaporphyrins: Reactive Cationic Porphyrinoids that Provide Isoporphyrin Analogues | |||||
| 言語 | en | |||||
| 著者 |
Chia, Wen Xi
× Chia, Wen Xi× Nishijo, Mayu× Kang, Seongsoo× Oh, Juwon× Nishimura, Tsubasa× Omori, Hiroto× Longevial, Jean‐François× Miyake, Yoshihiro× Kim, Dongho× Shinokubo, Hiroshi |
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| アクセス権 | ||||||
| アクセス権 | open access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||
| 権利 | ||||||
| 言語 | en | |||||
| 権利情報 | This is the peer reviewed version of the following article: [W. X. Chia, M. Nishijo, S. Kang, J. Oh, T. Nishimura, H. Omori, J.-F. Longevial, Y. Miyake, D. Kim, H. Shinokubo, Chem. Eur. J. 2020 , 26 , 2754.], which has been published in final form at [https://doi.org/10.1002/chem.201905402]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | aromaticity | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | conjugation | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | cycloaddition | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | methylation | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | porphyrinoids | |||||
| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | N‐Alkylation significantly changes the electronic and optical properties, as well as the reactivity of nitrogen‐containing π‐conjugated molecules. In this study, it is found that treating 5,15‐diazaporphyrins with methyl triflate selectively affords the corresponding N ‐methyl‐5,15‐diazaporphyrinium cations in good yield. N‐Methylation substantially alters the electronic properties and reactivity of diazaporphyrins. The electron‐accepting properties of the N ‐methyl‐5,15‐diazaporphyrinium cations are enhanced due to their lowered LUMO level. Stabilization of the LUMO energy enables regio‐ and stereoselective Diels–Alder reactions of the cationic diazaporphyrin with cyclopentadiene. N‐Methylation also enhances the acidity of the inner NH protons, and thus, allows facile deprotonation to provide nitrogen‐substituted isoporphyrin analogues with only one NH group in the central cavity. | |||||
| 言語 | en | |||||
| 内容記述 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | ファイル公開：2021-02-26 | |||||
| 言語 | ja | |||||
| 出版者 | ||||||
| 出版者 | Wiley | |||||
| 言語 | en | |||||
| 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 | |||||
| 出版タイプ | ||||||
| 出版タイプ | AM | |||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
| DOI | ||||||
| 関連タイプ | isVersionOf | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | https://doi.org/10.1002/chem.201905402 | |||||
| ISSN（print） | ||||||
| 収録物識別子タイプ | PISSN | |||||
| 収録物識別子 | 0947-6539 | |||||
| 書誌情報 |
en : Chemistry–A European Journal 巻 26, 号 12, p. 2754-2760, 発行日 2020-02-26 |
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| 著者版フラグ | ||||||
| 値 | author | |||||
