期刊
MACROMOLECULES
卷 51, 期 10, 页码 3874-3885出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.macromol.8b00161
关键词
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资金
- National Science Foundation of China [21774055, 51573076]
- Shenzhen Peacock Plan Project [KQTD20140630110339343]
- Shenzhen Key Lab funding [ZDSYS201505291525382]
- Shenzhen Basic Research Fund [JCYJ20160530185244662]
- Guangdong Natural Science Foundation [2015A030313900]
- South University of Science and Technology of China [FRG-SUSTC1501A-72]
- SUSTC Presidential Postdoctoral Fellowship
- Argonne Northwestern Solar Energy Research (ANSER) Center, an Energy Frontier Research Center - US Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC0001059]
- US DOE [DE-AC02-06CH11357]
- AFOSR Grant [FA9550-15-1-0044]
Head-to-head (HH) bithiophenes are typically avoided in polymer semiconductors since they engender undesirable steric repulsions, leading to a twisted backbone. While introducing electron-donating alkoxy chains can lead to intramolecular noncovalent S center dot center dot center dot O interactions, this comes at the cost of elevating the HOMOs and compromising polymer solar cell (PSC) performance. To address the limitation, a novel HH bithiophene featuring an electron-withdrawing ester functionality, 3-alkoxycarbonyl-3'-alkoxy-2,2'-bithiophene (TETOR), is synthesized. Single crystal diffraction reveals a planar TETOR conformation (versus highly twisted diester bithiophene), showing distinctive advantages of incorporating alkoxy on promoting backbone planarity. Compared to first-generation 3-alkyl-3'-alkoxy-2,2'-bithiophene (TRTOR), TETOR contains an additional planarizing (thienyl)S center dot center dot center dot O(carbonyl) interaction. Consequently, TETOR-based polymer (TffBT-TETOR) has greatly lower-lying FMOs, stronger aggregation, closer pi-stacking, and better miscibility with fullerenes versus the TRTOR-based counterpart (TffBT-TRTOR). These characteristics are attributed to the additional S center dot center dot center dot O interaction and electron-withdrawing ester substituent, which enhances backbone planarity, charge transport, and PSC performance. Thus, TffBT-TETOR-based PSCs exhibit an increased PCE of 10.08%, a larger V-oc of 0.76 V, and a higher J(sc) of 18.30 mA cm(-2) than the TffBT-TRTOR-based PSCs. These results demonstrate that optimizing intramolecular noncovalent S center dot center dot center dot O interactions by incorporating electron-withdrawing ester groups is a powerful strategy for materials invention in organic electronics.
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