Regioselective 1,2,3-bisazfulleroid: doubly N-bridged bisimino-PCBMs for polymer solar cells
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- Regioselective 1,2,3-bisazfulleroid: doubly N-bridged bisimino-PCBMs for polymer solar cells
- Kim, Boram; Lee, Junghoon; Seo, Jung Hwa; Wudl, Fred; Park, Sung Heum; Yang, Changduk
- Annulenes; Five-membered rings; Fullerene cages; Nitrogen atom; Polymer Solar Cells; Regio-selective; Visible region
- Issue Date
- ROYAL SOC CHEMISTRY
- JOURNAL OF MATERIALS CHEMISTRY, v.22, no.43, pp.22958 - 22963
- The direct bisaddition of methyl 5-azido-5-phenylpentanoate to C-60 takes place in the two neighboring pentagon-hexagon junctions of the same five-membered ring, yielding a regioselective bisazfulleroid, namely bisimino-PCBM. Because of its open annulene structure, this new bisheterofullerene is not only considered to be an isoelectronic analogue of pristine C-60, but also it is less symmetrical than previous reported mono-functionalized fullerenes, thereby displaying a stronger absorption in the visible region. The BHJ devices based on P3HT:bisimino-PCBM give a higher V-OC of 0.77 V relative to those using the PCBM in the literature, which can be attributed to the combination of the nature of the nitrogen atom and the open bridged mode in a fullerene cage. Furthermore, the bisimino-PCBM consisting exclusively of a doubly bridged open 11-membered ring with a hydroacenaphthylene perimeter is very new, therefore there is still plenty of room to establish better efficiencies of BHJ photovoltaic cells.
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