Benzo[ d ][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers
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.
- Research Organization:
- Argonne National Lab. (ANL), Argonne, IL (United States)
- Sponsoring Organization:
- National Science Foundation (NSF); US Air Force Office of Scientific Research (AFOSR); Northwestern University
- DOE Contract Number:
- AC02-06CH11357
- OSTI ID:
- 1330100
- Journal Information:
- Chemistry of Materials, Vol. 28, Issue 17; ISSN 0897-4756
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
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