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

Fingerprint

Derivatives
Semiconducting organic compounds
Diamines
Density functional theory
Single crystals
Semiconductor materials
X ray diffraction
tetracyanoquinodimethane
dicyanmethane

Keywords

  • 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. https://doi.org/10.1515/hc-2018-0136

Synthesis and properties of tetracyanoquinodimethane derivatives. / Zhu, Lei; Chang, Haizhen; Vavallo, Christopher L.; Jiang, Jianhui; Zeng, Zebing; Yang, Junliang; Smith, Mark D.; Miao, Shaobin.

In: Heterocyclic Communications, Vol. 24, No. 5, 25.10.2018, p. 249-254.

Research output: Contribution to journalArticle

Zhu, L, Chang, H, Vavallo, CL, Jiang, J, Zeng, Z, Yang, J, Smith, MD & Miao, S 2018, 'Synthesis and properties of tetracyanoquinodimethane derivatives', Heterocyclic Communications, vol. 24, no. 5, pp. 249-254. https://doi.org/10.1515/hc-2018-0136
Zhu L, Chang H, Vavallo CL, Jiang J, Zeng Z, Yang J et al. Synthesis and properties of tetracyanoquinodimethane derivatives. Heterocyclic Communications. 2018 Oct 25;24(5):249-254. https://doi.org/10.1515/hc-2018-0136
Zhu, Lei ; Chang, Haizhen ; Vavallo, Christopher L. ; Jiang, Jianhui ; Zeng, Zebing ; Yang, Junliang ; Smith, Mark D. ; Miao, Shaobin. / Synthesis and properties of tetracyanoquinodimethane derivatives. In: Heterocyclic Communications. 2018 ; Vol. 24, No. 5. pp. 249-254.
@article{506a11c889d24708a0681e45998a6e43,
title = "Synthesis and properties of tetracyanoquinodimethane derivatives",
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.",
keywords = "Lehnert reagent, TCNQ derivatives, organic semiconductor, single crystal X-ray structure",
author = "Lei Zhu and Haizhen Chang and Vavallo, {Christopher L.} and Jianhui Jiang and Zebing Zeng and Junliang Yang and Smith, {Mark D.} and Shaobin Miao",
year = "2018",
month = "10",
day = "25",
doi = "10.1515/hc-2018-0136",
language = "English (US)",
volume = "24",
pages = "249--254",
journal = "Heterocyclic Communications",
issn = "0793-0283",
publisher = "Walter de Gruyter GmbH & Co. KG",
number = "5",

}

TY - JOUR

T1 - Synthesis and properties of tetracyanoquinodimethane derivatives

AU - Zhu, Lei

AU - Chang, Haizhen

AU - Vavallo, Christopher L.

AU - Jiang, Jianhui

AU - Zeng, Zebing

AU - Yang, Junliang

AU - Smith, Mark D.

AU - Miao, Shaobin

PY - 2018/10/25

Y1 - 2018/10/25

N2 - 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.

AB - 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.

KW - Lehnert reagent

KW - TCNQ derivatives

KW - organic semiconductor

KW - single crystal X-ray structure

UR - http://www.scopus.com/inward/record.url?scp=85054395945&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85054395945&partnerID=8YFLogxK

U2 - 10.1515/hc-2018-0136

DO - 10.1515/hc-2018-0136

M3 - Article

AN - SCOPUS:85054395945

VL - 24

SP - 249

EP - 254

JO - Heterocyclic Communications

JF - Heterocyclic Communications

SN - 0793-0283

IS - 5

ER -