2,7-Disubstituted 1,3,6,8-tetraazabenzopyrenes: Synthesis, characterization, optical and electrochemical properties

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Abstract

The syntheses of 2,7-diamino-1,3,6,8-tetraazabenzopyrene framework was achieved through CuI-catalyzed double annulation of 1,4-diiodoanthraquinone with guanidine. In addition, the preparation of series of 2,7-disubstituted 1,3,6,8-tetraazabenzopyrenes functionalized by NR 2 , C[dbnd]O, Cl, alkoxy and phenoxy groups with good yields was achieved through the simple transformations such as diazotization, alkylation and nucleophilic aromatic substitution. The properties of 1,3,6,8-tetraazabenzopyrenes synthesized were studied by DFT-calculations, optical and photoluminescence spectroscopy, cyclic voltammetry and light-induced EPR spectroscopy. The luminescence of amino derivatives is quenched in acidic solutions depending on the degree of protonation.

Original languageEnglish
Pages (from-to)219-227
Number of pages9
JournalDyes and Pigments
Volume168
DOIs
Publication statusPublished - 1 Sep 2019

Keywords

  • Alkylation
  • Double peri-annulation
  • Nucleophilic substitution
  • Photophysical properties
  • Tetraazabenzopyrenes
  • PERFORMANCE
  • HETEROACENES
  • MOLECULAR DESIGN
  • TRANSISTORS
  • FLUORESCENCE
  • NITROGEN
  • BASIS-SETS
  • EMISSION
  • PROBE
  • ORGANIC PHOTOVOLTAICS

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