Gram-Scale Synthesis of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane (F2-TCNQ)

En Chih Liu; Joseph J. Topczewski

doi:10.1021/acs.joc.0c00053

Gram-Scale Synthesis of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane (F₂-TCNQ)

En Chih Liu
, Joseph J. Topczewski

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The molecule 2,5-difluoro-7,7,8,8-tetracyanoquinodimethane (F₂-TCNQ) is an organic semiconductor with many promising properties, including high charge mobility (μ). However, an efficient gram-scale synthesis of F₂-TCNQ has not been fully documented. Herein, we report a synthesis of F₂-TCNQ via a three-step sequence that affords F₂-TCNQ in 58% cumulative yield. This synthesis was used to prepare more than 1 g of F₂-TCNQ.

Original language	English (US)
Pages (from-to)	4560-4564
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	85
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.0c00053
State	Published - Mar 20 2020

Bibliographical note

Funding Information:
We thank Prof. Aaron Massari (UMN) for suggesting this target. This work was supported by the University of Minnesota.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

Publisher link

10.1021/acs.joc.0c00053

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Cite this

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title = "Gram-Scale Synthesis of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane (F2-TCNQ)",

abstract = "The molecule 2,5-difluoro-7,7,8,8-tetracyanoquinodimethane (F2-TCNQ) is an organic semiconductor with many promising properties, including high charge mobility (μ). However, an efficient gram-scale synthesis of F2-TCNQ has not been fully documented. Herein, we report a synthesis of F2-TCNQ via a three-step sequence that affords F2-TCNQ in 58\% cumulative yield. This synthesis was used to prepare more than 1 g of F2-TCNQ.",

author = "Liu, \{En Chih\} and Topczewski, \{Joseph J.\}",

note = "Funding Information: We thank Prof. Aaron Massari (UMN) for suggesting this target. This work was supported by the University of Minnesota. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

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AB - The molecule 2,5-difluoro-7,7,8,8-tetracyanoquinodimethane (F2-TCNQ) is an organic semiconductor with many promising properties, including high charge mobility (μ). However, an efficient gram-scale synthesis of F2-TCNQ has not been fully documented. Herein, we report a synthesis of F2-TCNQ via a three-step sequence that affords F2-TCNQ in 58% cumulative yield. This synthesis was used to prepare more than 1 g of F2-TCNQ.

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