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The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
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Tethered tertiary amines as solid-state n-type dopants for solution-processable organic semiconductors.

Boris Russ1,2, Maxwell J Robb3, Bhooshan C Popere4

  • 1Department of Chemical and Biomolecular Engineering , University of California , Berkeley , CA 94720 , USA.

Chemical Science
|June 15, 2018
PubMed
Summary

Stable n-type doping in organic electronics is improved by tethered tertiary amine groups. These groups, formed during processing, effectively generate free electron carriers in various organic semiconductor systems.

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Area of Science:

  • Organic electronics
  • Materials science
  • Semiconductor physics

Background:

  • Facile and stable n-type doping remains a challenge for organic electronic devices.
  • Localizing dopants near conductive cores can enhance doping efficiency.
  • Previous work utilized trimethylammonium functionalization with hydroxide counterions linked to perylene diimide cores.

Purpose of the Study:

  • To identify the primary mechanism behind effective n-type doping in thin films.
  • To explore the general applicability of tethered tertiary amine groups as n-doping motifs.
  • To expand molecular design strategies for n-type organic electronic materials.

Main Methods:

  • Investigating the role of tethered tertiary amine moieties in thin film processing.
  • Evaluating the n-doping capabilities of tethered tertiary amines with various small molecule systems.
  • Characterizing the generation of free electron carriers in solid-state organic materials.

Main Results:

  • The formation of tethered tertiary amine moieties during thin film processing is the key driver for effective doping, contrary to prior assumptions.
  • Tethered tertiary amine groups serve as potent and versatile n-doping motifs.
  • Successful generation of free electron carriers was achieved with perylene diimide, naphthalene diimide, diketopyrrolopyrrole, and fullerene derivatives.

Conclusions:

  • Tethered tertiary amine groups are a powerful and general strategy for n-type doping in organic electronics.
  • This molecular design approach significantly enhances the performance of organic electronic devices.
  • The findings provide a foundation for developing next-generation n-type organic semiconductor materials.