High-Performance Organic Solar Cells Containing Pyrido[2,3-b]quinoxaline-Core-Based Small-Molecule Acceptors with Optimized Orbit Overlap Lengths and Molecular Packing

Tongle Xu, Zhenghui Luo, Ruijie Ma, Zhanxiang Chen, Top Archie Dela Peña, Heng Liu, Qi Wei, Mingjie Li, Cai'e Zhang, Jiaying Wu, Xinhui Lu, Gang Li, Chuluo Yang

Research output: Journal article publicationJournal articleAcademic researchpeer-review

44 Citations (Scopus)

Abstract

The central core in A-DA1D-A-type small-molecule acceptor (SMAs) plays an important role in determining the efficiency of organic solar cells (OSCs), while the principles governing the efficient design of SMAs remain elusive. Herein, we developed a series of SMAs with pyrido[2,3-b]quinoxaline (PyQx) as new electron-deficient unit by combining with the cascade-chlorination strategy, namely Py1, Py2, Py3, Py4 and Py5. The introduction of chlorine atoms reduces the intramolecular charge transfer effects but elevates the LUMO values. Density functional theory (DFT) reveals that Py2 with ortho chlorine substituted PyQx and Py5 with two chlorine atoms yield larger dipole moments and smaller π⋅⋅⋅π stacking distances, as compared with the other three acceptors. Moreover, Py2 shows the strongest light absorption capability induced by extended orbit overlap lengths and more efficient packing structures in the dimers. These features endow the best device performance of Py2 due to the better molecular packing and aggregation behaviors, more suitable domain sizes with better exciton dissociation and charge recombination. This study highlights the significance of incorporating large dipole moments, small π⋅⋅⋅π stacking distances and extended orbit overlap lengths in dimers into the development of high-performance SMAs, providing insight into the design of efficient A-DA1D-A-type SMAs for OSCs.

Original languageEnglish
Article numbere202304127
JournalAngewandte Chemie - International Edition
Volume62
Issue number30
DOIs
Publication statusPublished - 24 Jul 2023

Keywords

  • Chlorination
  • Molecular Packing
  • Pyrido[2,3-b]Quinoxaline
  • Small-Molecule Acceptor
  • Solar Cells

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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