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

Atsuro Takai, Masayuki Takeuchi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)44-51
Number of pages8
JournalBulletin of the Chemical Society of Japan
Issue number1
Publication statusPublished - 2018


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