Synthesis and properties of tetracyanoquinodimethane derivatives

Lei Zhu, Haizhen Chang, Christopher L. Vavallo, Jianhui Jiang, Zebing Zeng, Junliang Yang, Mark D. Smith, Shaobin Miao

Research output: Contribution to journalArticle


Two new aza-acenequinone derivatives 4 and 5 were prepared by cyclocondensation of diamines 2 and 3 with bis(triisopropylsilyl)-dialkynyl-l,2-dione 1. Further reactions of compounds 4 and 5 with malononitrile using the Lehnert reagent afforded corresponding tetracyanoquinodimethane (TCNQ) derivatives 6 and 7. Compounds 4, 6 and 7 were characterized by single crystal X-ray diffraction techniques. Compounds 6 and 7 were studied electrochemically and photochemically. Density functional theory (DFT) calculations on compounds 6 and 7 indicate that both compounds have the potential to be candidates for organic semiconductor materials.

Original languageEnglish (US)
Pages (from-to)249-254
Number of pages6
JournalHeterocyclic Communications
Issue number5
Publication statusPublished - Oct 25 2018
Externally publishedYes



  • Lehnert reagent
  • TCNQ derivatives
  • organic semiconductor
  • single crystal X-ray structure

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Zhu, L., Chang, H., Vavallo, C. L., Jiang, J., Zeng, Z., Yang, J., ... Miao, S. (2018). Synthesis and properties of tetracyanoquinodimethane derivatives. Heterocyclic Communications, 24(5), 249-254.