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ACS Appl Mater Interfaces. 2018 Nov 21;10(46):39992-40000. doi: 10.1021/acsami.8b15923. Epub 2018 Nov 6.

Chlorine Atom-Induced Molecular Interlocked Network in a Non-Fullerene Acceptor.

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Department of Chemistry and Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen 518055 , P. R. China.
Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices , South China University of Technology , Guangzhou 510640 , P. R. China.


The differences between the introduction of chlorine and fluorine atoms to small-molecule acceptors were deeply investigated. From the single-crystal structures of three molecules, the Cl-substitution intervention into the molecular configuration and packing mainly lies in three aspects as follows: single molecule configuration, one direction of the intermolecular arrangement, and three-dimensional (3D) molecular packing. First, the introduction of the chlorine atom in IDIC-4Cl leads to a more planar molecular configuration than IDIC-4H and IDIC-4F because of the formation of a molecular interlocked network induced by the strong Cl···S intermolecular interactions. Second, IDIC-4Cl shows the closest π-π stacking distance and the smallest dihedral angle (0°) between adjacent molecules to form ideal J-aggregation, which should be beneficial for charge transportation between different connected molecules in this direction. Finally, the interlocked interactions between Cl and S atoms lead to a highly ordered 3D molecular packing, in which the end groups will form an ideal overlapped packing among different molecules, whereas the other two analogues with H or F show less ordered packing of their 1,1-dicyanomethylene-3-indanone ending groups. Organic solar cells based on IDIC-4Cl show the highest power conversion efficiency (PCE) of 9.24%, whereas the PCEs of IDIC-4H- and IDIC-4F-based devices are 4.57 and 7.10%, respectively.


J-aggregation; chlorine; molecular interlocked network; non-fullerene acceptors; single crystals


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