Chinese Journal of Organic Chemistry >
Synthesis and Optoelectronic Properties of A-D-A Type Small Molecule Acceptors Containing Isatin-Fused Acenaphthenequinone Imide Terminal Groups
Received date: 2020-11-30
Revised date: 2021-01-05
Online published: 2021-02-07
Supported by
National Natural Science Foundation of China(21875202); Hunan Provincial Natural Science Foundation(2018JJ1024); and the Science and Technology Planning Project of Hunan Province(2017RS3048)
Two novel A-D-A type small molecule acceptors (A1 andA2) are designed and synthesized by adopting isatin- fused acenaphthenequinone imide or nitrogen-doped isatin-fused acenaphthoquinone imide as the terminal groups and indacenodithiophene derivative as the donor core. The effect of pyridal nitrogen on the molecular structure, optical absorption, and energy level of A1 and A2 is comparatively studied by combining density functional theory (DFT) calculation. In comparison with A1, the incorporation of pyridal nitrogen into A2 not only improves backbone coplanarity, but also achieves 27 nm red-shift in the charge transfer peak of solution absorption. Moreover, the investigation of electrochemical analysis and DFT calculation indicates that the pyridal nitrogen-containing A2 exhibits enhanced electron affinity, thereby leading to deeper- lying energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) as compared to its counterpart (A1). Finally, non-fullerene solar cells containing PBDB-T:A1 or PBDB-T:A2 (mass ratio 1:1) blend films are fabricated by usingA1 or A2 as the electron acceptor material and commercial available PBDB-T as the donor material. The highest energy conversion efficiencies of 5.19% and 6.19% are demonstrated for A1 and A2, respectively.
Sai Wu , Wuxi Tao , Guo Wang , Bin Zhao , Huajie Chen . Synthesis and Optoelectronic Properties of A-D-A Type Small Molecule Acceptors Containing Isatin-Fused Acenaphthenequinone Imide Terminal Groups[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 2019 -2028 . DOI: 10.6023/cjoc202011038
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