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

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

Find It

Find It at U of M Libraries

Cite this

@article{ce3f7d3963c94fbf9b8979c20d4eded1,

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.",

year = "2020",

month = mar,

day = "20",

doi = "10.1021/acs.joc.0c00053",

language = "English (US)",

volume = "85",

pages = "4560--4564",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Gram-Scale Synthesis of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane (F2-TCNQ)

AU - Liu, En Chih

AU - Topczewski, Joseph J.

N1 - 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.

PY - 2020/3/20

Y1 - 2020/3/20

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85082143669&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85082143669&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.0c00053

DO - 10.1021/acs.joc.0c00053

M3 - Article

C2 - 32118430

AN - SCOPUS:85082143669

SN - 0022-3263

VL - 85

SP - 4560

EP - 4564

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -