Catalyst-Free Reaction of Ethynyl-π-Extended Electron Acceptors with Amines

Access this Article

Search this Article

Author(s)

Abstract

<p>Imide- or amide-based π-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 π-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 amine-addition reaction, various amino-functionalized asymmetric and symmetric π-systems were obtained in a designed manner.</p>

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 91(1), 44-51, 2018

    The Chemical Society of Japan

Codes

  • NII Article ID (NAID)
    130006309057
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • ISSN
    0009-2673
  • NDL Article ID
    028756706
  • NDL Call No.
    Z53-B35
  • Data Source
    NDL  J-STAGE 
Page Top