Issue 3, 2016

Tethered tertiary amines as solid-state n-type dopants for solution-processable organic semiconductors

Abstract

A scarcity of stable n-type doping strategies compatible with facile processing has been a major impediment to the advancement of organic electronic devices. Localizing dopants near the cores of conductive molecules can lead to improved efficacy of doping. We and others recently showed the effectiveness of tethering dopants covalently to an electron-deficient aromatic molecule using trimethylammonium functionalization with hydroxide counterions linked to a perylene diimide core by alkyl spacers. In this work, we demonstrate that, contrary to previous hypotheses, the main driver responsible for the highly effective doping observed in thin films is the formation of tethered tertiary amine moieties during thin film processing. Furthermore, we demonstrate that tethered tertiary amine groups are powerful and general n-doping motifs for the successful generation of free electron carriers in the solid-state, not only when coupled to the perylene diimide molecular core, but also when linked with other small molecule systems including naphthalene diimide, diketopyrrolopyrrole, and fullerene derivatives. Our findings help expand a promising molecular design strategy for future enhancements of n-type organic electronic materials.

Graphical abstract: Tethered tertiary amines as solid-state n-type dopants for solution-processable organic semiconductors

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Nov. 2015
Accepted
06 Dec. 2015
First published
09 Dec. 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 1914-1919

Author version available

Tethered tertiary amines as solid-state n-type dopants for solution-processable organic semiconductors

B. Russ, M. J. Robb, B. C. Popere, E. E. Perry, C. Mai, S. L. Fronk, S. N. Patel, T. E. Mates, G. C. Bazan, J. J. Urban, M. L. Chabinyc, C. J. Hawker and R. A. Segalman, Chem. Sci., 2016, 7, 1914 DOI: 10.1039/C5SC04217H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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