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

Abstract

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
Volume24
Issue number5
DOIs
StatePublished - Oct 25 2018
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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  • Cite this

    Zhu, L., Chang, H., Vavallo, C. L., Jiang, J., Zeng, Z., Yang, J., Smith, M. D., & Miao, S. (2018). Synthesis and properties of tetracyanoquinodimethane derivatives. Heterocyclic Communications, 24(5), 249-254. https://doi.org/10.1515/hc-2018-0136