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

Number of Access:345（2025-08-28 17:32 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/100185

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Title
Synthesis and Characterization of an Air-Stable Tin(IV) β-Tetracyanoisophlorin Complex: Enhanced Antiaromaticity through Metal Complexation.
Creator
ORCID
0000-0002-7394-2838 0000-0002-7394-2838
CreatorName
Sugimura, Haruna
CreatorName
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
CreatorName
Yamashita, Ken-ichi
Subject
Antiaromaticity
Isophlorins
Porphyrinoids
Tin complexes
X-ray crystallography
Description
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.
Abstract
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.
Publisher
John Wiley and Sons Inc
Source Title
Asian Journal of Organic Chemistry
Page
e202400550
Date of Issued
2025-01-08
Language
English
Handle URL
https://hdl.handle.net/11094/100185
eISSN
21935815
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1002/ajoc.202400550
Access Rights
open access
CopyRight
This article is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
oaire:version
Version of Record
Category
学術雑誌論文 Journal Article