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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-fluoroisoBT 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 BTquaterthiophene 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 highperformance optoelectronic semiconductors with P3 exhibiting hole mobilities surpassing 0.7 cm 2/(V s) in field-effect transistors and power conversion efficiencies of 9% in bulk-heterojunction solar cells.

Authors:
; ; ; ; ; ; ; ; ; ; ; ; ;
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
National Science Foundation (NSF); US Air Force Office of Scientific Research (AFOSR); Northwestern University
OSTI Identifier:
1330100
DOE Contract Number:
AC02-06CH11357
Resource Type:
Journal Article
Resource Relation:
Journal Name: Chemistry of Materials; Journal Volume: 28; Journal Issue: 17
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 33 ADVANCED PROPULSION SYSTEMS

Citation Formats

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, and Facchetti, Antonio. Benzo[ d ][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers. United States: N. p., 2016. Web. doi: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. United States. doi: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, and Facchetti, Antonio. Tue . "Benzo[ d ][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers". United States. doi:10.1021/acs.chemmater.6b02813.
@article{osti_1330100,
title = {Benzo[ d ][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers},
author = {Chen, Zhihua and Brown, Jennifer and Drees, Martin and Seger, Mark and Hu, Yan and Xia, Yu and Boudinet, Damien and McCray, Meko and Delferro, Massimiliano and Marks, Tobin J. and Liao, Chuang-Yi and Ko, Chung-Wen and Chang, Yi-Ming and Facchetti, Antonio},
abstractNote = {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-fluoroisoBT 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 BTquaterthiophene 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 highperformance 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.},
doi = {10.1021/acs.chemmater.6b02813},
journal = {Chemistry of Materials},
number = 17,
volume = 28,
place = {United States},
year = {Tue Sep 13 00:00:00 EDT 2016},
month = {Tue Sep 13 00:00:00 EDT 2016}
}