Catalyst-free reaction of ethynyl-p-extended electron acceptors with amines

Atsuro Takai, Masayuki Takeuchi

研究成果: Article査読

9 被引用数 (Scopus)

抄録

Imide- or amide-based p-systems, as represented by naphthalenediimides (NDIs), perylenediimides (PDIs), or diketopyrrolopyrroles (DPPs), have been extensively studied owing to their characteristic optical properties, their electronic structures, and so forth. Here, we present syntheses of NDIs, a PDI, and a DPP with ethynyl substituents, and their use as new building blocks for the synthesis of amino-functionalized electron-accepting p-conjugated systems. The reaction between the ethynyl group of the electron acceptor and an amine proceeds almost quantitatively, without a catalyst, to give a Michael-addition-type product that shows remarkable changes in its optical properties, redox properties, and dipole moment. The progress of the reaction can be visually monitored in various media. On the basis of a kinetic analysis of the amineaddition reaction, various amino-functionalized asymmetric and symmetric p-systems were obtained in a designed manner.

本文言語English
ページ(範囲)44-51
ページ数8
ジャーナルBulletin of the Chemical Society of Japan
91
1
DOI
出版ステータスPublished - 2018
外部発表はい

ASJC Scopus subject areas

  • 化学 (全般)

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