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The crucial role of end group planarity for fused-ring electron acceptors in organic solar cells (Conference Presentation)

Paper Abstract

Newly developed fused-ring electron acceptors (FREAs) have proven to be an effective class of materials for extending the absorption window and boosting the efficiency of organic photovoltaics (OPVs). While numerous FREA small molecules have been developed, there is surprisingly little structural diversity among high performance FREAs in literature. For example, of the high efficiency electron acceptors reported, the vast majority utilize derivatives of 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (INCN) as the acceptor moiety. It has been postulated that the high electron mobility exhibited by FREA molecules with INCN end groups is a result of close π-π stacking between the neighboring planar INCN groups, forming an effective charge transport pathway between molecules. To explore this as a design rationale for electron acceptors, we synthesized a new fused-ring electron acceptor, IDTCF, which has methyl substituents out of plane to the conjugated acceptor backbone. These methyl groups hinder packing and expand the π-π stacking distance by ~ 1 Å, but this change doesn’t affect the optical or electrochemical properties of the individual acceptor molecule. Overall, our results show that intermolecular interactions (especially π-π stacking between end groups) play a crucial role in performance of FREAs. We demonstrated that the planarity of the acceptor unit is of paramount importance as even minor deviations in end group distance are enough to disrupt crystallinity and cripple device performance.

Paper Details

Date Published: 10 September 2019
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Proc. SPIE 11094, Organic, Hybrid, and Perovskite Photovoltaics XX, 110940Y (10 September 2019); doi: 10.1117/12.2529500
Show Author Affiliations
Jeromy J. Rech, The Univ. of North Carolina at Chapel Hill (United States)
Nicole Bauer, The Univ. of North Carolina at Chapel Hill (United States)
David Dirkes, The Univ. of North Carolina at Chapel Hill (United States)
Joseph Kaplan, The Univ. of North Carolina at Chapel Hill (United States)
Huotain Zhang, Linköping Univ. (Sweden)
Zhengxing Peng, North Carolina State Univ. (United States)
Long Ye, North Carolina State Univ. (United States)
Shubin Liu, The Univ. of North Carolina at Chapel Hill (United States)
Harald Ade, North Carolina State Univ. (United States)
Feng Gao, Linköping Univ. (Sweden)
Wei You, The Univ. of North Carolina at Chapel Hill (United States)


Published in SPIE Proceedings Vol. 11094:
Organic, Hybrid, and Perovskite Photovoltaics XX
Zakya H. Kafafi; Paul A. Lane; Kwanghee Lee; Ana Flávia Nogueira, Editor(s)

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