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 language | English |
|---|---|
| Pages (from-to) | 6390-6400 |
| Number of pages | 11 |
| Journal | Chemistry of Materials |
| Volume | 28 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - Sep 13 2016 |
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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 journal › Article
}
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.
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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
AN - SCOPUS:84987654814
VL - 28
SP - 6390
EP - 6400
JO - Chemistry of Materials
JF - Chemistry of Materials
SN - 0897-4756
IS - 17
ER -