Synthesis of Thiophene-annulated Naphthalene Diimide-based Small-Molecular Acceptors via Two-step C−H Activation

Rukiya Matsidik, Kazuo Takimiya

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Thiophene-annulated naphthalene diimide (NTI)-based molecules have recently emerged as an important class of n-type electronic materials. However, their synthesis has predominantly been achieved by Stille or Suzuki coupling reactions despite the presence of a potential C−H bond in NTI. Additionally, the synthesis of NTI or more generally mono-functionalization of naphthalene diimide (NDI) starts with a cumbersome bromination that results in a low yield, is unselective, and requires tedious purification. We herein thus address these issues via a two-step C−H activation: a rhodium-catalyzed direct C−H iodinization is first presented for NDI, followed by establishing an efficient direct arylation protocol for NTI with high yield and robustness. Coupling of up to four NTI units on a benzene or pyrene core is demonstrated along with other aryl bromide substrates. All the herein reported NTI-based small molecules showed n-type semiconductor behavior under air.

Original languageEnglish
Pages (from-to)1651-1656
Number of pages6
JournalChemistry - An Asian Journal
Volume14
Issue number10
DOIs
Publication statusPublished - 2019 May 15

Keywords

  • C−H activation
  • arylation
  • mono-halogenation
  • naphthalene diimides
  • rhodium catalysts

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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