Ferrocene-Substituted Naphthalenediimide with Broad Absorption and Electron-Transport Properties in the Segregated-Stack Structure

Atsuro Takai, Daisuke Sakamaki, Shu Seki, Yoshitaka Matsushita, Masayuki Takeuchi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

A new naphthalenediimide (NDI) molecule, where two ferrocene (Fc) units were directly attached to both imide nitrogens (Fc-NDI-Fc), was synthesized. The Fc units provide high crystallinity to Fc-NDI-Fc with good solubility to conventional organic solvents. The Fc units also work as electron-donating substituents, in contrast to the electron-deficient NDI unit, resulting in broad charge-transfer absorption of Fc-NDI-Fc from the UV region to 1500 nm in the solid state. The crystal structure analysis revealed that Fc-NDI-Fc formed a segregated-stack structure. The DFT calculation based on the crystal structure showed that the NDI π-orbitals extended over two axes. The extended π-network of the NDI units led to the electron-transport properties of Fc-NDI-Fc, which was confirmed using a flash-photolysis time-resolved microwave conductivity technique.

Original languageEnglish
Pages (from-to)7385-7388
Number of pages4
JournalChemistry - A European Journal
Volume22
Issue number22
DOIs
Publication statusPublished - 2016 May 23
Externally publishedYes

Keywords

  • charge transfer
  • electron transport
  • electronic structure
  • ferrocene
  • stacking interactions

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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