Ladder-Type Thienoacenaphthopyrazine-Based Molecules: Synthesis, Properties, and Application to Construct HighPerformance Polymer for Organic Solar Cells

Han, Pengwei1; Lin, Man1; Jiang, Qiuju1; Ning, Haijun1; Su, Mingbin1; Dang, Li1; He, Feng2; Wu, Qinghe1

2022-06-01

10.31635/ccschem.022.202201839

CCS CHEMISTRY   Impact Factor & Quartile

2096-5745

We present a new design strategy to synthesize ladder-type thienoacenaphthopyrazine (TAP)-based monomers through two different coupling reactions from starting material 5,6-dibromoacenaphthylene1,2-dione. By bringing varous electron-deficient groups together (such as five-membered aromatic rings, pyrazine, fluorine, and thiadiazols), this new family of molecules exhibits good stability in ambient conditions and easily tunes the electronic, photophysical and film-forming properties of polymers. The unique molecular shape with its extended pi-conjugated backbone perpendicular to the polymer chain, offers a remarkable platform for the development of a semiconducting polymer with rare geometry. The planar and enlarged conjugated backbone enables TAP-based copolymers PTAP1 and PTAP2 to exhibit distinguishing solubility properties that are different from small-molecule-based polymers, indicating the advantages of novel ladder-type monomers. Their insolubility in chloroform supports orthogonal solvent processing to fabricate layer-by-layer organic solar cells (LBL-OSCs). Owing to its shorter pi-pi stacking distance, higher hole mobility, and more favorable phase separation caused bymultifluorine substitution, polymer PTAP1-based LBL-OSC exhibits the highest efficiency of 17.14% by using Y6-BO as the electron acceptor while the efficiency for the PTAP2-based device is 14.20%. This high efficiency indicates the tremendous potential of these novel building units.

ladder-type monomer thienoacenaphthopyrazine polymer donor organic solar cell

ESCI

English

Others

National Natural Science Foundation of China[22179076] ; Fund for Zhujiang Young Scholar[18220203] ; Natural Science Foundation of Guangdong Province[2022A1515011803] ; Department of Education of Guangdong Province["2021KCXTD032","2019KCXTD007"]

Chemistry

Chemistry, Multidisciplinary

WOS:000933740600001

CHINESE CHEMICAL SOC

Web of Science

1.Shantou Univ, Key Lab Preparat & Applicat Ordered Struct Mat Gu, Dept Chem, Shantou, Guangdong, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Shenzhen, Peoples R China

Han, Pengwei,Lin, Man,Jiang, Qiuju,et al. Ladder-Type Thienoacenaphthopyrazine-Based Molecules: Synthesis, Properties, and Application to Construct HighPerformance Polymer for Organic Solar Cells[J]. CCS CHEMISTRY,2022.

Han, Pengwei.,Lin, Man.,Jiang, Qiuju.,Ning, Haijun.,Su, Mingbin.,...&Wu, Qinghe.(2022).Ladder-Type Thienoacenaphthopyrazine-Based Molecules: Synthesis, Properties, and Application to Construct HighPerformance Polymer for Organic Solar Cells.CCS CHEMISTRY.

Han, Pengwei,et al."Ladder-Type Thienoacenaphthopyrazine-Based Molecules: Synthesis, Properties, and Application to Construct HighPerformance Polymer for Organic Solar Cells".CCS CHEMISTRY (2022).