Crystal Engineering of Dual Channel p/n Organic Semiconductors by Complementary HydrogenBonding

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 semico...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 53; no. 8; pp. 2138 - 2142
Main Authors Black, Hayden T, Perepichka, Dmitrii F
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 17.02.2014
EditionInternational ed. in English
Subjects
Channels
Devices
Electronics
Heterojunctions
Hydrogen bonding
Organic semiconductors
R&D
Research & development
Self assembly
Semiconductors
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Summary: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 Hbonding. [PUBLICATION ABSTRACT]
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201310902