Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 8, Pages 2138-2142Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310902
Keywords
heterojunction; hydrogen bonds; organic field-effect transistors; semiconductors; supramolecular chemistry
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Funding
- NSERC
- NanoQuebec
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The supramolecular arrangement of organic semiconductors in the solid state is as critical for their device properties as the molecular structure, but is much more difficult to control. To enable supramolecular design of semiconducting materials, we introduced dipyrrolopyridine as a new donor semiconductor capable of complementary hydogenbonding with naphthalenediimide acceptors. Through a combination of solution, crystallographic, and device studies, we show that the self-assembly driven by Hbonding a)modulates the charge-transfer interactions between the donor and acceptor, b)allows for precise control over the solid-state packing, and c)leads to a combination of the charge-transport properties of the individual components. The predictive power of this approach was demonstrated in the synthesis of three new coassembled materials which show both hole and electron transport in single-crystal field-effect transistors. These studies provide a foundation for advanced solid-state engineering in organic electronics, capitalizing on the complementary H bonding.
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