期刊
ACS APPLIED MATERIALS & INTERFACES
卷 6, 期 16, 页码 14533-14542出版社
AMER CHEMICAL SOC
DOI: 10.1021/am503812f
关键词
Isoindigo; photophysics; J-aggregation; solid-state organization; organic solar cells
资金
- ONR's Photovoltaic Program [N00014-11-10328]
- NSF through the Princeton Center for Complex Materials [DMR-0819860]
- NIH/NIGMS [DMR-0936384]
- PCCM-MRSEC
- NDSEG
- L'Oreal Women in Science postdoctoral fellowship
- NSF
We designed and synthesized a series of isoindigo-based derivatives to investigate how chemical structure modification at both the 6,6'- and 5,5'-positions of the core with electron-rich and electron-poor moieties affect photophysical and redox properties as well as their solid-state organization. Our studies reveal that 6,6'-substitution on the isoindigo core results in a stronger intramolecular charge transfer band due to strong electronic coupling between the 6,6'-substituent and the core, whereas 5,5'-substitution induces a weaker CT band that is more sensitive to the electronic nature of the substituents. In the solid state, 6,6'-derivatives generally form J-aggregates, whereas 5,5'-derivatives form H-aggregates. With only two branched ethylhexyl side chains, the 6,6'-derivatives form organized lamellar structures in the solid state. The incorporation of electron-rich benzothiophene, BT, substituents further enhances ordering, likely because of strong intermolecular donor-acceptor interactions between the BT substituent and the electron-poor isoindigo core on neighboring compounds. Collectively, the enhanced photophysical properties and solid-state organization of the 6,6'-benzothiophene substituted isoindigo derivative compared to the other isoindigo derivatives examined in this study resulted in solar cells with higher power conversion efficiencies when blended with a fullerene derivative.
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