Modular Synthesis of Triarylamines and Poly(triarylamine)s through a Radical Mechanism

The modular synthesis of triarylamines and poly(triarylamine)s has been achieved by using diarylamines and electron-rich arenes as the building blocks. Through the modulation of reaction temperatures, the stepwise assembly of bis-triarylamines could be realized efficiently. Furthermore, the multiple aminated polyphenols were rapidly constructed by a single step. This method should find applications in the synthesis of triarylamine-type photocatalysts and optoelectronic materials.

Abstract

A modular protocol for the triarylamine synthesis has been developed using diarylamines and electron-rich arenes, such as phenols, as the building blocks. The KI/KIO₄ system proves to be highly efficient for the cross-dehydrogenative coupling of phenothiazines/phenoxazines with phenols/anilines. A wide range of functional groups attached to both coupling partners were well tolerated. Through the manipulation of reaction temperatures, the sequential assembly of bis-triarylamines could be achieved to provide the unsymmetrically bis-aminated phenols efficiently. Furthermore, the multiple aminated polyphenols were rapidly constructed in good to high yields by a single operation.

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