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  1. B200 工学部/工学研究科
  2. B200a 雑誌掲載論文
  3. 学術雑誌

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/2237/00032315
f3e80685-d96f-4a5a-891c-1eed5de1ccb4
名前 / ファイル ライセンス アクション
manuscript.pdf manuscript (2.4 MB)
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

WEKO 99456

en Chia, Wen Xi

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Nishijo, Mayu

× Nishijo, Mayu

WEKO 99457

en Nishijo, Mayu

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Kang, Seongsoo

× Kang, Seongsoo

WEKO 99458

en Kang, Seongsoo

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Oh, Juwon

× Oh, Juwon

WEKO 99459

en Oh, Juwon

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Nishimura, Tsubasa

× Nishimura, Tsubasa

WEKO 99460

en Nishimura, Tsubasa

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Omori, Hiroto

× Omori, Hiroto

WEKO 99461

en Omori, Hiroto

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Longevial, Jean‐François

× Longevial, Jean‐François

WEKO 99462

en Longevial, Jean‐François

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Miyake, Yoshihiro

× Miyake, Yoshihiro

WEKO 99463

en Miyake, Yoshihiro

Search repository
Kim, Dongho

× Kim, Dongho

WEKO 99464

en Kim, Dongho

Search repository
Shinokubo, Hiroshi

× Shinokubo, Hiroshi

WEKO 99465

en Shinokubo, Hiroshi

Search repository
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 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
内容記述タイプ Abstract
内容記述
内容記述 ファイル公開:2021-02-26
言語 ja
内容記述タイプ Other
出版者
言語 en
出版者 Wiley
言語
言語 eng
資源タイプ
資源タイプresource http://purl.org/coar/resource_type/c_6501
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
著者版フラグ
値 author
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