A Bulky Aryl–Substituted Acridinium Salt: 10-(3,5-Di-tert-butylphenyl)-9-mesitylacridinium Tetrafluoroborate

9-Mesitylacridinium salts are widely recognized as efficient organic photoredox catalysts owing to their strong excited-state oxidizing power and stability under visible-light irradiation. In this study, a new mesityl acridinium derivative bearing a di-tert-butylphenyl substituent on the nitrogen atom was synthesized. The introduction of tert-butyl groups on the N-aryl moiety was primarily aimed at improving solubility and chemical stability of the acridinium salt. Starting from a 9(10H)-acridinone precursor, the target compound was obtained in high overall yield through a concise synthetic sequence. The synthesis consists of a copper-catalyzed C–N coupling reaction to install the aryl substituent on the nitrogen atom, followed by a Grignard reaction and subsequent acid treatment to afford the corresponding acridinium salt. All transformations proceeded smoothly, providing efficient access to the desired novel acridinium derivative. This work presents a practical example of the structural modification of mesitylacridinium derivatives directed toward enhanced solubility and stability, and provides a useful synthetic platform for the preparation of structurally diverse acridinium salts.

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Publication Details

Journal
Molbank
Published
2026-04-14
DOI
https://doi.org/10.3390/m2164
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

A Bulky Aryl–Substituted Acridinium Salt: 10-(3,5-Di-tert-butylphenyl)-9-mesitylacridinium Tetrafluoroborate

Yuki Itabashi, Kei Ohkubo
Molbank
Radical Photochemical Reactions
article

A Bulky Aryl–Substituted Acridinium Salt: 10-(3,5-Di-tert-butylphenyl)-9-mesitylacridinium Tetrafluoroborate

Yuki Itabashi, Kei Ohkubo
article en

Abstract

9-Mesitylacridinium salts are widely recognized as efficient organic photoredox catalysts owing to their strong excited-state oxidizing power and stability under visible-light irradiation. In this study, a new mesityl acridinium derivative bearing a di-tert-butylphenyl substituent on the nitrogen atom was synthesized. The introduction of tert-butyl groups on the N-aryl moiety was primarily aimed at improving solubility and chemical stability of the acridinium salt. Starting from a 9(10H)-acridinone precursor, the target compound was obtained in high overall yield through a concise synthetic sequence. The synthesis consists of a copper-catalyzed C–N coupling reaction to install the aryl substituent on the nitrogen atom, followed by a Grignard reaction and subsequent acid treatment to afford the corresponding acridinium salt. All transformations proceeded smoothly, providing efficient access to the desired novel acridinium derivative. This work presents a practical example of the structural modification of mesitylacridinium derivatives directed toward enhanced solubility and stability, and provides a useful synthetic platform for the preparation of structurally diverse acridinium salts.

MolbankVol. 2026(2)
The University of Osaka (JP)
Japan Society for the Promotion of Science
Openalex Percentile: Top 25%
Radical Photochemical Reactions
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A Bulky Aryl–Substituted Acridinium Salt: 10-(3,5-Di-tert-butylphenyl)-9-mesitylacridinium Tetrafluoroborate — Yuki Itabashi, Kei Ohkubo · Molbank (2026) | TGRS Research Map | TGRS