Regioselective 1,2,3-bisazfulleroid: Doubly N-bridged bisimino-PCBMs for polymer solar cells

Boram Kim, Junghoon Lee, Jung Hwa Seo, Fred Wudl, Sung Heum Park, Changduk Yang

Research output: Contribution to journalArticlepeer-review

12 Scopus citations


The direct bisaddition of methyl 5-azido-5-phenylpentanoate to C60takes 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 C60, 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 VOCof 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.

Original languageEnglish
Pages (from-to)22958-22963
Number of pages6
JournalJournal of Materials Chemistry
Issue number43
StatePublished - 21 Nov 2012


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