Two Cationic Antiaromatic Free-Base Corroles

The synthesis of free-base antiaromatic porphyrinoids remains a challenging task. Herein we report the first preparation of two cationic free-base antiaromatic corroles, <b>BC(H</b><sub><b>2</b></sub><b>)</b><sup><b>+</b></sup> (containing two NH moieties, slightly saddle-shaped) and <b>BC(H</b><sub><b>4</b></sub><b>)</b><sup><b>3+</b></sup> (containing four NH moieties, severely distorted saddle-shaped), utilizing a strategy of β-annulated benzene rings to suppress side reactions. The antiaromatic character of <b>BC(H</b><sub><b>2</b></sub><b>)</b><sup><b>+</b></sup> and <b>BC(H</b><sub><b>4</b></sub><b>)</b><sup><b>3+</b></sup> is robustly supported by crystallographic analysis, spectroscopic evidence, and theoretical calculations.

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Publication Details

Journal
Organic Letters
Published
2025-09-19
DOI
https://doi.org/10.1021/acs.orglett.5c03111
Primary Topic
Porphyrin and Phthalocyanine Chemistry
Type
article
Field-Weighted Citation Impact
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article

Two Cationic Antiaromatic Free-Base Corroles

Fan Wu, Chulin Qu, Hidemitsu Uno, Zhen Shen et al.
Organic Letters
Porphyrin and Phthalocyanine Chemistry
article

Two Cationic Antiaromatic Free-Base Corroles

Fan Wu, Chulin Qu, Hidemitsu Uno, Zhen Shen, Pengfei Li
article en

Abstract

The synthesis of free-base antiaromatic porphyrinoids remains a challenging task. Herein we report the first preparation of two cationic free-base antiaromatic corroles, <b>BC(H</b><sub><b>2</b></sub><b>)</b><sup><b>+</b></sup> (containing two NH moieties, slightly saddle-shaped) and <b>BC(H</b><sub><b>4</b></sub><b>)</b><sup><b>3+</b></sup> (containing four NH moieties, severely distorted saddle-shaped), utilizing a strategy of β-annulated benzene rings to suppress side reactions. The antiaromatic character of <b>BC(H</b><sub><b>2</b></sub><b>)</b><sup><b>+</b></sup> and <b>BC(H</b><sub><b>4</b></sub><b>)</b><sup><b>3+</b></sup> is robustly supported by crystallographic analysis, spectroscopic evidence, and theoretical calculations.

Organic LettersVol. 27(39)
Nanjing Normal University (CN), Collaborative Innovation Center of Advanced Microstructures (CN), Ehime University (JP), Graduate School USA (US), Nanjing University (CN)
Openalex Percentile: Top 80%
Porphyrin and Phthalocyanine Chemistry
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