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Synthesis 2018; 50(04): 764-771
DOI: 10.1055/s-0036-1591871
paper
© Georg Thieme Verlag Stuttgart · New York

Second-Generation Azafullerene Monoadducts as Electron Acceptors in Bulk Heterojunction Solar Cells

Michael Bothe
a   Institute of Organic Chemistry and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany   Email: max.vondelius@uni-ulm.de
,
María Pilar Montero-Rama
b   Department d’Enginyeria Electrònica, Elèctrica i Automàtica, Universitat Rovira i Virgili, Avda. Països Catalans 16, 43007 Tarragona, Spain   Email: lluis.marsal@urv.cat
,
Aurélien Viterisi
b   Department d’Enginyeria Electrònica, Elèctrica i Automàtica, Universitat Rovira i Virgili, Avda. Països Catalans 16, 43007 Tarragona, Spain   Email: lluis.marsal@urv.cat
,
Werther Cambarau
c   Institute of Chemical Research of Catalonia (ICIQ), Avda. Països Catalans 26, 43007 Tarragona, Spain
,
Caterina Stenta
b   Department d’Enginyeria Electrònica, Elèctrica i Automàtica, Universitat Rovira i Virgili, Avda. Països Catalans 16, 43007 Tarragona, Spain   Email: lluis.marsal@urv.cat
,
Emilio Palomares
c   Institute of Chemical Research of Catalonia (ICIQ), Avda. Països Catalans 26, 43007 Tarragona, Spain
,
Lluis F. Marsal*
b   Department d’Enginyeria Electrònica, Elèctrica i Automàtica, Universitat Rovira i Virgili, Avda. Països Catalans 16, 43007 Tarragona, Spain   Email: lluis.marsal@urv.cat
,
Max von Delius  *
a   Institute of Organic Chemistry and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany   Email: max.vondelius@uni-ulm.de
› Author AffiliationsThis 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).
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Publication History

Received: 03 November 2017

Accepted: 27 November 2017

Publication Date:
11 January 2018 (online)

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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 relationships

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    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591871.
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