Synthesis and characterization of oxadisilole-fused 1H-benzo[f]indazoles and 1H-naphtho[2,3-f]indazoles

Yajuan Zhang, Xuyan Ma, Yali Chen*, Xuanming Chen, Lei Guo, Weiguo Cao, Jie Chen, Ricky M S WONG

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Oxadisilole-fused 1H-benzo[f]- and 1H-naphtho[2,3-f]indazoles have been synthesized by the 1,3-dipolar cycloaddition reactions of benzo- or naphtho-oxabicycloalkenes with nitrile imines generated in situ from N-arylhydrazonoyl chlorides followed by deoxygenation and aromatization. The photophysical, redox and thermal properties of these compounds have been characterized. Some of the indazoles show potential as deep-blue emitters for OLED applications as a result of their high fluorescence quantum yields and good thermal stabilities. Oxadisilole-fused 1H-benzo[f]- and 1H-naphtho[2,3-f] indazoles have been synthesized by the 1,3-dipolar cycloaddition of benzo- or naphtho-oxabicycloalkenes with nitrile imines followed by deoxygenation and aromatization. Their photophysical, redox and thermal properties show that some of the indazoles show potential as deep-blue emitters for OLED applications.

Original languageEnglish
Pages (from-to)3005-3012
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number15
DOIs
Publication statusPublished - May 2013

Scopus Subject Areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

User-Defined Keywords

  • Cyclic voltammetry
  • Cycloaddition
  • Fluorescence
  • Fused-ring systems
  • Heterocycles

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