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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(03): 229-234
DOI: 10.1055/s-0040-1714283
Focus Issue: Curved Organic π-Systems
Short Communication

Bowl-Shaped Naphthalimide-Annulated Corannulene as Nonfullerene Acceptor in Organic Solar Cells

Kaan Menekse‡   ‡
a   Center for Nanosystems Chemistry, Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany
,
Rebecca Renner‡   ‡
b   Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
,
Bernhard Mahlmeister
a   Center for Nanosystems Chemistry, Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany
,
Matthias Stolte
a   Center for Nanosystems Chemistry, Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany
b   Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
,
Frank Würthner 
a   Center for Nanosystems Chemistry, Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany
b   Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
› Author Affiliations Funding Information We are grateful for financial support from the Deutsche Forschungsgemeinschaft (Grant Wu 317/20-1) as well as the Bavarian Research Program “Solar Technologies Go Hybrid”.
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Abstract

An electron-poor bowl-shaped naphthalimide-annulated corannulene with branched alkyl residues in the imide position was synthesized by a palladium-catalyzed cross-coupling annulation sequence. This dipolar compound exhibits strong absorption in the visible range along with a low-lying LUMO level at –3.85 eV, enabling n-type charge transport in organic thin-film transistors. Furthermore, we processed inverted bulk-heterojunction solar cells in combination with the two donor polymers PCE–10 and PM6 to achieve open-circuit voltages up to 1.04 V. By using a blend of the self-assembled naphthalimide-annulated corannulene and PCE–10, we were able to obtain a power conversion efficiency of up to 2.1%, which is to the best of our knowledge the highest reported value for a corannulene-based organic solar cell to date.

Key words

corannulene - curved π-systems - bulk-heterojunction solar cells - nonfullerene acceptors - aggregation

Supporting Information

Supporting information for this article is available online at http://doi.org/10.1055/s-0040-1714283.


‡ Kaan Menekse and Rebecca Renner contributed equally to this work.


Supplementary Material



Publication History

Received: 25 May 2020

Accepted: 12 June 2020

Article published online:
09 September 2020

© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

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