期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 34, 页码 14303-14307出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202004989
关键词
contorted aromatics; optoelectronic materials; organic electronics; perylene diimides
资金
- U.S. Department of Energy [DE-SC0014563]
- Feodor Lynen Fellowship of the Alexander von Humboldt Society
- Columbia Nano Initiative Postdoctoral Fellowship
- NSFC [21761142011, 21772123, 51502173]
- Shanghai Government [18JC1412900, 18DZ2254200]
- International Joint Laboratory of Resource Chemistry (IJLRC)
- U.S. Department of Energy (DOE) [DE-SC0014563] Funding Source: U.S. Department of Energy (DOE)
This study explores a new mode of contortion in perylene diimides where the molecule is bent, like a bow, along its long axis. These bowed PDIs were synthesized through a facile fourfold Suzuki macrocyclization with aromatic linkers and a tetraborylated perylene diimide that introduces strain and results in a bowed structure. By altering the strings of the bow, the degree of bending can be controlled from flat to highly bent. Through spectroscopy and quantum chemical calculations, it is demonstrated that the energy of the lowest unoccupied orbital can be controlled by the degree of bending in the structures and that the energy of the highest occupied orbital can be controlled to a large extent by the constitution of the aromatic linkers. The important finding is that the bowing results not only in red-shifted absorptions but also more facile reductions.
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