Fused Pyrazine- and Carbazole-Containing Azaacenes: Synthesis and Properties

Hailiang Liao, Chengyi Xiao, Mahesh Kumar Ravva, Liping Yao, Yaping Yu, Yinghe Yang, Weimin Zhang, Lei Zhang, Zhengke Li, Iain McCulloch, Wan Yue

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A new family of azaacenes has been designed and synthesized by incorporating the electron-withdrawing sp2-hybridized nitrogen of pyrazine and electron-donating nitrogen of carbazole in a molecular skeleton. Two different conjugated lengths of 8-ring aza-nonacene and 10-ring aza-undecene have been achieved by an efficient condensation reaction. The unique optoelectronic properties of these molecules were investigated using both experimental and theoretical techniques. The azaacenes show visible-region absorption and near-infrared (NIR) fluorescence. These compounds can serve as hole-transport semiconductors for solution-processed organic field-effect transistors (OFETs). Single-crystal transistor devices of one of the aza-nonacenes exhibit hole charge transport behavior with a hole mobility of 0.07 cm2/Vs and an on/off current ratio of 1.3x106.

Original languageEnglish (US)
Pages (from-to)1257-1262
Number of pages6
JournalChemPlusChem
Volume84
Issue number9
DOIs
StatePublished - Sep 1 2019
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry

Keywords

  • azaacenes
  • carbazole
  • fused systems
  • pyrazines
  • semiconductor materials

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