Synthesis and Optoelectronic Properties of A-D-A Type Small Molecule Acceptors Containing Isatin-Fused Acenaphthenequinone Imide Terminal Groups

doi:10.6023/cjoc202011038

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2019-2028.DOI: 10.6023/cjoc202011038 Previous Articles Next Articles

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含靛红并苊醌二甲酰亚胺端基的A-D-A型小分子受体材料的合成及其光电性质研究

吴赛¹, 陶吴晞¹, 王果¹, 赵斌¹^,^*(), 陈华杰¹^,^*()

1 湘潭大学化学学院环境友好化学与应用教育部重点实验室湘潭 411105

收稿日期:2020-11-30 修回日期:2021-01-05 发布日期:2021-02-07
通讯作者: 赵斌, 陈华杰
基金资助:
国家自然科学基金(21875202); 湖南省自然科学基金(2018JJ1024); 湖南省科技厅计划(2017RS3048)

Synthesis and Optoelectronic Properties of A-D-A Type Small Molecule Acceptors Containing Isatin-Fused Acenaphthenequinone Imide Terminal Groups

Sai Wu¹, Wuxi Tao¹, Guo Wang¹, Bin Zhao¹^,^*(), Huajie Chen¹^,^*()

1 Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105 China

Received:2020-11-30 Revised:2021-01-05 Published:2021-02-07
Contact: Bin Zhao, Huajie Chen
About author:
* Corresponding authors. E-mail: chenhjoe@163.com;
E-mail: xtuzb@163.com
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)

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Abstract

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.

Key words: acenaphthenequinone imide, A-D-A small molecule acceptor, non-fullerene solar cells, energy conversion efficiency

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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.

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Fig. & Tab. 10

Figure 1. Chemical structure of small molecule acceptor material (A1and A2) and well-known polymer donor material (PBDB-T) and their corresponding device structure of non-fullerene solar cells

Figure 2. Synthetic route of compounds A1 and A2

Compd.	λ_max/nm		λ_max^onset/nm	E_g^a/eV	E_LUMO^b/eV	E_HOMO^c/eV	E_g^d/eV	E_LUMO^e/eV	E_HOMO^e/eV
Compd.	Solution	Film	λ_max^onset/nm	E_g^a/eV	E_LUMO^b/eV	E_HOMO^c/eV	E_g^d/eV	E_LUMO^e/eV	E_HOMO^e/eV
A1	428, 665	433, 700	825	1.50	–3.94	–5.32	1.42	–3.21	–5.08
A2	430, 692	436, 733	858	1.45	–3.97	–5.34	1.37	–3.29	–5.09

Table 1. Optical, electrochemical and DFT-calculated data of A1 and A2

Figure 3. (a) Molar extinction coefficients of A1 and A2 in chloroform solution, and (b) absorption spectra of A1 and A2 in chloroform solution and as solid-state film

Figure 4. Optimized molecular structures, frontier molecular orbitals, and HOMO/LUMO energy levels

Figure 5. (a) Cyclic voltammogram curves and (b) energy level diagram of A-D-A small molecule acceptors A1 and A2

共混膜	V_OC/V	J_SC/(mA?cm^–2)	FF/%	PCE/%	μ_h/(cm²?V^–1?s^–1)	μ_e/(cm²?V^–1?s^–1)	μ_h/μ_e
PBDB-T:A1	0.96	8.94	59.22	5.19	2.20×10^-4	5.92×10^-5	3.72
PBDB-T:A2	0.89	11.09	62.73	6.19	2.52×10^-4	2.29×10^-4	1.10

Table 2. Optimal photovoltaic parameters of non-fullerene solar cell devices based on different acceptors

Figure 6. (a) J-V curves and (b) EQE spectra of non-fullerene solar cell devices based on PBDB-T/A1 or PBDB-T/A2 blend films

Figure 7. (a) Hole mobility and (b) electron mobility curves based on PBDB-T/A1 or PBDB-T/A2 blend films

Figure 8. Surface morphology of blend films (a) PBDB-T/A1 and (b) PBDB-T/A2

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含靛红并苊醌二甲酰亚胺端基的A-D-A型小分子受体材料的合成及其光电性质研究

Synthesis and Optoelectronic Properties of A-D-A Type Small Molecule Acceptors Containing Isatin-Fused Acenaphthenequinone Imide Terminal Groups

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