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Synthesis 2018; 50(04): 764-771
DOI: 10.1055/s-0036-1591871
DOI: 10.1055/s-0036-1591871
paper
Second-Generation Azafullerene Monoadducts as Electron Acceptors in Bulk Heterojunction Solar Cells
This work was supported by the Deutsche Forschungsgemeinschaft (DFG) (SFB 953, ‘Synthetic Carbon Allotropes’), the Daimler und Benz Stiftung (grant no. 32-12/13), the Spanish Ministry of Economy, Industry and Competitiveness (MEIC) [TEC2015-71324-R and TEC2015-71915-REDT (MINECO/FEDER)], and the Catalan Institution for Research and Advanced Studies (ICREA) (ICREA ‘Academia Award’, AGAUR 2017 SGR 1527).Further Information
Publication History
Received: 03 November 2017
Accepted: 27 November 2017
Publication Date:
11 January 2018 (online)
Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry
Abstract
Four new azafullerene monoadducts (DPS-C59N, HDP-C59N, DBOP-C59N, DHOP-C59N) have been prepared and applied as electron acceptors in solution-processed bulk heterojunction solar cells. The four compounds were designed so that their solubility in organic solvents was maximized and that structure–property comparisons could be drawn with a previously synthesized azafullerene electron acceptor. With the photovoltaic devices that were prepared from the four azafullerenes and polymeric electron donor PTB7 we found that only one of the four new electron acceptors resulted in a power conversion efficiency that exceeded the one observed with a previously reported azafullerene monoadduct. Atomic force microscopy and electron mobility measurements suggest that azafullerenes bearing two alkyl chains lead to non-optimal film morphologies as well as electron mobilities and that future efforts should focus on single n-alkyl substitution.
Key words
fullerenes - azafullerenes - electrophilic aromatic substitution - organic photovoltaics - structure-property relationshipsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591871.
- Supporting Information
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