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Issue 48, 2019
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Naphthalene core-based noncovalently fused-ring electron acceptors: effects of linkage positions on photovoltaic performances

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Abstract

Two mutually isomeric noncovalently fused-ring electron acceptors (NC-FREAs) NOC6F-1 and NOC6F-2 containing two cyclopentadithiophene (CPDT) moieties linked at the 2,6- and 1,5-positions, respectively, of the naphthalene ring were designed and synthesized for organic solar cells (OSCs). Intramolecular noncovalent S⋯O interactions were introduced into NOC6F-1 and NOC6F-2. The tiny structural variation in NOC6F-1 and NOC6F-2 by just changing the linkage positions affects largely their molecular configuration, absorption, molecular packing, charge transport and photovoltaic performance. Compared to NOC6F-2, NOC6F-1 exhibits smaller distortions between cyclopentadithiophene and the naphthalene unit, leading to an extended conjugation and enhanced π–π stacking. NOC6F-2 exhibits a poor planarity, which restricts the electron delocalization as well as dense π–π stacking in the film form. When blended with PBDB-T, NOC6F-1 exhibits more orderly stacking along both the out-of-plane and in-plane directions than NOC6F-2. OSCs based on PBDB-T:NOC6F-2 merely showed a power conversion efficiency (PCE) of 6.74% with lower Jsc and FF values. OSCs based on NOC6F-1 achieved a higher Jsc of 17.08 mA cm−2 and an FF of 65.79%, thus leading to a significantly enhanced PCE of 10.62%. These results indicate that use of the acceptor molecules with a planar molecular backbone is an important design strategy for NC-FREAs.

Graphical abstract: Naphthalene core-based noncovalently fused-ring electron acceptors: effects of linkage positions on photovoltaic performances

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Supplementary files

Article information


Submitted
11 Sep 2019
Accepted
19 Nov 2019
First published
21 Nov 2019

J. Mater. Chem. C, 2019,7, 15141-15147
Article type
Communication

Naphthalene core-based noncovalently fused-ring electron acceptors: effects of linkage positions on photovoltaic performances

R. Zheng, Q. Guo, D. Hao, C. Zhang, W. Xue, H. Huang, C. Li, W. Ma and Z. Bo, J. Mater. Chem. C, 2019, 7, 15141
DOI: 10.1039/C9TC05013B

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