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

24 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

ASJC Scopus subject areas

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

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    Chen, Z., Brown, J., Drees, M., Seger, M., Hu, Y., Xia, Y., Boudinet, D., McCray, M., Delferro, M., Marks, T. J., Liao, C. Y., Ko, C. W., Chang, Y. M., & Facchetti, A. (2016). Benzo[d][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers. Chemistry of Materials, 28(17), 6390-6400. https://doi.org/10.1021/acs.chemmater.6b02813