Synthesis and Characterization of an Air-Stable Tin(IV) β-Tetracyanoisophlorin Complex: Enhanced Antiaromaticity through Metal Complexation.

Sugimura, Haruna; Nakajima, Kana; Yamashita, Ken-ichi

Asian Journal of Organic Chemistry, 2025, e202400550

アクセス数:336件（2025-07-22 14:34 集計）

固定URL: https://hdl.handle.net/11094/100185

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タイトル
Synthesis and Characterization of an Air-Stable Tin(IV) β-Tetracyanoisophlorin Complex: Enhanced Antiaromaticity through Metal Complexation.
著者
ORCID
0000-0002-7394-2838 0000-0002-7394-2838
著者名
Sugimura, Haruna
著者名
Nakajima, Kana
NRID
1000040468145 1000040468145
ORCID
0000-0001-7270-1234 0000-0001-7270-1234
researchmap permalink
ken1-yamashi ken1-yamashi
Scopus Author ID
35792834600 35792834600
著者名
Yamashita, Ken-ichi
キーワード等
Antiaromaticity
Isophlorins
Porphyrinoids
Tin complexes
X-ray crystallography
内容
Sugimura H., Nakajima K., Yamashita K.i. Synthesis and Characterization of an Air-Stable Tin(IV) β-Tetracyanoisophlorin Complex: Enhanced Antiaromaticity through Metal Complexation.. Asian Journal of Organic Chemistry , (2025); https://doi.org/10.1002/ajoc.202400550.
抄録
Isophlorins, which are two-electron reduced porphyrins, have garnered significant interest because of their potential antiaromaticity and unique electronic properties. However, the isolation of stable antiaromatic isophlorins remains challenging because they are prone to oxidation or reduction to the corresponding aromatic molecules, or are structurally distorted, resulting in loss of antiaromaticity. Here, we report the synthesis and characterization of a Sn(IV) β-tetracyanoisophlorin complex obtained through two-electron reduction of the corresponding Sn(IV) β-tetracyanoporphyrin complex. This Sn(IV) complex exhibits enhanced antiaromaticity owing to its highly planar structure, facilitated by the central Sn atom. X-ray crystal diffraction analysis revealed that the Sn(IV) isophlorin complex contains two methoxy groups as axial ligands and that it exists as a divalent anion, demonstrating the oxophilic nature of the Sn(IV) isophlorin complexes. Notably, this Sn(IV) isophlorin complex is stable under air, distinguishing it from previously reported Si(IV) and Ge(IV) isophlorin complexes without cyano groups. This study thus presents the first isolation of an air-stable metal complex of antiaromatic isophlorin, opening new possibilities for exploring the unique properties of antiaromatic porphyrinoids for various applications, including catalysis and materials science.
出版者
John Wiley and Sons Inc
収録物名
Asian Journal of Organic Chemistry
ページ
e202400550
刊行年月
2025-01-08
言語
英語
ハンドルURL
https://hdl.handle.net/11094/100185
eISSN
21935815
関連情報 (isIdenticalTo)
DOI (出版社版)
https://doi.org/10.1002/ajoc.202400550
アクセス権
open access
権利情報
This article is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
出版タイプ
Version of Record
カテゴリ
学術雑誌論文 Journal Article