Benzo[d][1,2,3]thiadiazole (isoBT)

Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers

Zhihua Chen, Jennifer Brown, Martin Drees, Mark Seger, Yan Hu, Yu Xia, Damien Boudinet, Meko McCray, Massimiliano Delferro, Tobin J Marks, Chuang Yi Liao, Chung Wen Ko, Yi Ming Chang, Antonio Facchetti

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Benzo[d][2,1,3]thiadiazole (BT) is a markedly electron-deficient heterocycle widely employed in the realization of organic semiconductors for applications spanning transistors, solar cells, photodetectors, and thermoelectrics. In this contribution, we implement the corresponding isomer, benzo[d][1,2,3]thiadiazole (isoBT), along with new 6-fluoro-isoBT and 5,6-difluoro-isoBT units as synthons for constructing alternating copolymers with tetrathiophene (P1-P3). New isoBT-based small molecules as well as the corresponding BT-quaterthiophene based polymers (P4-P6) are synthesized and characterized to probe architectural, electronic structural, and device performance differences between the two families. The results demonstrate that isoBT complements BT in enabling high-performance optoelectronic semiconductors with P3 exhibiting hole mobilities surpassing 0.7 cm2/(V s) in field-effect transistors and power conversion efficiencies of 9% in bulk-heterojunction solar cells.

Original languageEnglish
Pages (from-to)6390-6400
Number of pages11
JournalChemistry of Materials
Volume28
Issue number17
DOIs
Publication statusPublished - Sep 13 2016

Fingerprint

Thiadiazoles
Semiconducting polymers
Structural analysis
Solar cells
Hole mobility
Semiconducting organic compounds
Field effect transistors
Photodetectors
Isomers
Optoelectronic devices
Conversion efficiency
Heterojunctions
Polymers
Transistors
Copolymers
Semiconductor materials
Molecules
Electrons

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

Cite this

Benzo[d][1,2,3]thiadiazole (isoBT) : Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers. / Chen, Zhihua; Brown, Jennifer; Drees, Martin; Seger, Mark; Hu, Yan; Xia, Yu; Boudinet, Damien; McCray, Meko; Delferro, Massimiliano; Marks, Tobin J; Liao, Chuang Yi; Ko, Chung Wen; Chang, Yi Ming; Facchetti, Antonio.

In: Chemistry of Materials, Vol. 28, No. 17, 13.09.2016, p. 6390-6400.

Research output: Contribution to journalArticle

Chen, Z, Brown, J, Drees, M, Seger, M, Hu, Y, Xia, Y, Boudinet, D, McCray, M, Delferro, M, Marks, TJ, Liao, CY, Ko, CW, Chang, YM & Facchetti, A 2016, 'Benzo[d][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers', Chemistry of Materials, vol. 28, no. 17, pp. 6390-6400. https://doi.org/10.1021/acs.chemmater.6b02813
Chen, Zhihua ; Brown, Jennifer ; Drees, Martin ; Seger, Mark ; Hu, Yan ; Xia, Yu ; Boudinet, Damien ; McCray, Meko ; Delferro, Massimiliano ; Marks, Tobin J ; Liao, Chuang Yi ; Ko, Chung Wen ; Chang, Yi Ming ; Facchetti, Antonio. / Benzo[d][1,2,3]thiadiazole (isoBT) : Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers. In: Chemistry of Materials. 2016 ; Vol. 28, No. 17. pp. 6390-6400.
@article{9a6fd86498c54ed792caeac3dcf317bb,
title = "Benzo[d][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers",
abstract = "Benzo[d][2,1,3]thiadiazole (BT) is a markedly electron-deficient heterocycle widely employed in the realization of organic semiconductors for applications spanning transistors, solar cells, photodetectors, and thermoelectrics. In this contribution, we implement the corresponding isomer, benzo[d][1,2,3]thiadiazole (isoBT), along with new 6-fluoro-isoBT and 5,6-difluoro-isoBT units as synthons for constructing alternating copolymers with tetrathiophene (P1-P3). New isoBT-based small molecules as well as the corresponding BT-quaterthiophene based polymers (P4-P6) are synthesized and characterized to probe architectural, electronic structural, and device performance differences between the two families. The results demonstrate that isoBT complements BT in enabling high-performance optoelectronic semiconductors with P3 exhibiting hole mobilities surpassing 0.7 cm2/(V s) in field-effect transistors and power conversion efficiencies of 9{\%} in bulk-heterojunction solar cells.",
author = "Zhihua Chen and Jennifer Brown and Martin Drees and Mark Seger and Yan Hu and Yu Xia and Damien Boudinet and Meko McCray and Massimiliano Delferro and Marks, {Tobin J} and Liao, {Chuang Yi} and Ko, {Chung Wen} and Chang, {Yi Ming} and Antonio Facchetti",
year = "2016",
month = "9",
day = "13",
doi = "10.1021/acs.chemmater.6b02813",
language = "English",
volume = "28",
pages = "6390--6400",
journal = "Chemistry of Materials",
issn = "0897-4756",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Benzo[d][1,2,3]thiadiazole (isoBT)

T2 - Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers

AU - Chen, Zhihua

AU - Brown, Jennifer

AU - Drees, Martin

AU - Seger, Mark

AU - Hu, Yan

AU - Xia, Yu

AU - Boudinet, Damien

AU - McCray, Meko

AU - Delferro, Massimiliano

AU - Marks, Tobin J

AU - Liao, Chuang Yi

AU - Ko, Chung Wen

AU - Chang, Yi Ming

AU - Facchetti, Antonio

PY - 2016/9/13

Y1 - 2016/9/13

N2 - Benzo[d][2,1,3]thiadiazole (BT) is a markedly electron-deficient heterocycle widely employed in the realization of organic semiconductors for applications spanning transistors, solar cells, photodetectors, and thermoelectrics. In this contribution, we implement the corresponding isomer, benzo[d][1,2,3]thiadiazole (isoBT), along with new 6-fluoro-isoBT and 5,6-difluoro-isoBT units as synthons for constructing alternating copolymers with tetrathiophene (P1-P3). New isoBT-based small molecules as well as the corresponding BT-quaterthiophene based polymers (P4-P6) are synthesized and characterized to probe architectural, electronic structural, and device performance differences between the two families. The results demonstrate that isoBT complements BT in enabling high-performance optoelectronic semiconductors with P3 exhibiting hole mobilities surpassing 0.7 cm2/(V s) in field-effect transistors and power conversion efficiencies of 9% in bulk-heterojunction solar cells.

AB - Benzo[d][2,1,3]thiadiazole (BT) is a markedly electron-deficient heterocycle widely employed in the realization of organic semiconductors for applications spanning transistors, solar cells, photodetectors, and thermoelectrics. In this contribution, we implement the corresponding isomer, benzo[d][1,2,3]thiadiazole (isoBT), along with new 6-fluoro-isoBT and 5,6-difluoro-isoBT units as synthons for constructing alternating copolymers with tetrathiophene (P1-P3). New isoBT-based small molecules as well as the corresponding BT-quaterthiophene based polymers (P4-P6) are synthesized and characterized to probe architectural, electronic structural, and device performance differences between the two families. The results demonstrate that isoBT complements BT in enabling high-performance optoelectronic semiconductors with P3 exhibiting hole mobilities surpassing 0.7 cm2/(V s) in field-effect transistors and power conversion efficiencies of 9% in bulk-heterojunction solar cells.

UR - http://www.scopus.com/inward/record.url?scp=84987654814&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84987654814&partnerID=8YFLogxK

U2 - 10.1021/acs.chemmater.6b02813

DO - 10.1021/acs.chemmater.6b02813

M3 - Article

VL - 28

SP - 6390

EP - 6400

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 17

ER -