Tethered tertiary amines as solid-state n-type dopants for solution-processable organic semiconductors [electronic resource].
- Washington, D.C. : United States. Dept. of Energy. Office of Basic Energy Sciences, 2015. and Oak Ridge, Tenn. : Distributed by the Office of Scientific and Technical Information, U.S. Dept. of Energy
- Physical Description:
- pages 1,914-1,919 : digital, PDF file
- Additional Creators:
- Lawrence Berkeley National Laboratory, United States. Department of Energy. Office of Basic Energy Sciences, National Science Foundation (U.S.), and United States. Department of Energy. Office of Scientific and Technical Information
- Restrictions on Access:
- Free-to-read Unrestricted online access
- 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.
- Published through SciTech Connect., 12/09/2015., "ark:/13030/qt9sd314c2", Chemical Science 7 3 ISSN 2041-6520; CSHCBM AM, and Boris Russ; Maxwell J. Robb; Bhooshan C. Popere; Erin E. Perry; Cheng-Kang Mai; Stephanie L. Fronk; Shrayesh N. Patel; Thomas E. Mates; Guillermo C. Bazan; Jeffrey J. Urban; Michael L. Chabinyc; Craig J. Hawker; Rachel A. Segalman.
- Funding Information:
- AC02-05CH11231 and DMR 1121053
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