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Crystal Engineering of Dual Channel p/n Organic Semiconductors by Complementary Hydrogen Bonding
Author(s) -
Black Hayden T.,
Perepichka Dmitrii F.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310902
Subject(s) - crystal engineering , supramolecular chemistry , organic semiconductor , semiconductor , materials science , acceptor , hydrogen bond , transistor , crystal (programming language) , nanotechnology , organic electronics , charge (physics) , crystallography , crystal structure , optoelectronics , chemistry , molecule , computer science , electrical engineering , condensed matter physics , organic chemistry , physics , programming language , engineering , quantum mechanics , voltage
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 hydogen bonding with naphthalenediimide acceptors. Through a combination of solution, crystallographic, and device studies, we show that the self‐assembly driven by H bonding 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.