10-(3,5-Di-tert-butylphenyl)-9-Mesitylacridinium Tetrafluoroborate

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Authors: Yuki Itabashi, Kei Ohkubo
Cited by: 1

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 ir-radiation. 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. The target compound was obtained in high overall yield starting from a 9(10H)-acridinone precursor 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 structural modification of mesitylacridinium derivatives directed toward enhanced solubility and stability, and provides a useful synthetic plat-form for the preparation of structurally diverse acridinium salts.

Fields of Study & Subjects

Radical Photochemical Reactions Photochromic and Fluorescence Chemistry Luminescence and Fluorescent Materials

Publication details

Journal / source
Preprints.org
Publisher
MDPI AG
Publication date
6 March 2026
Document type
Preprint