Understanding the Properties of Tailor-Made Self-Assembled Monolayers with Embedded Dipole Moments for Interface Engineering

Michael Gärtner, Eric Sauter, Giulia Nascimbeni, Andreas Petritz, Adrian Wiesner, Martin Kind, Tarek Abu-Husein, Michael Bolte, Barbara Stadlober, Egbert Zojer, Andreas Terfort, Michael Zharnikov

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

Abstract

Self-assembled monolayers (SAMs) are frequently used for interfacial dipole engineering in organic electronics and photovoltaics. This is mostly done by the attachment of dipolar tail groups onto the molecular backbone of the SAM precursors. The alternative concept of embedded dipoles involves the incorporation of polar group(s) into the backbone. This allows one to decouple the tuning of the electrostatic properties of the SAM from the chemical identity of the SAM-ambient interface. Here we present design and synthesis of particularly promising SAM precursors utilizing this concept. These precursors feature the thiol-docking group and a short heteroaromatic backbone, consisting of a nonpolar phenyl ring and a polar pyrimidine group, embedded in two opposite orientations. Packing density, molecular orientation, structure, and wetting properties of the SAMs on Au substrates are found to be nearly independent of their chemical structure, as shown by a variety of complementary experimental techniques. A further important property of the studied SAMs is their good electrical conductivity, enabling their application as electrode modifiers for low-contact resistances in organic electronic devices. Of particular interest are also the electronic properties of the SAMs, which were monitored by Kelvin probe and high-resolution X-ray photoelectron spectroscopy measurements. To obtain a fundamental understanding of these properties at an atomistic level, the experiments were combined with state-of-the-art band structure calculations. These not only confirm the structural properties of the films but also explain how the C 1s core-level binding energies of the various atoms are controlled by their chemical environments in conjunction with the local distribution of the electrostatic potential within the monolayer.

Originalspracheenglisch
Seiten (von - bis)28757-28774
Seitenumfang18
FachzeitschriftJournal of Physical Chemistry C
Jahrgang122
Ausgabenummer50
DOIs
PublikationsstatusVeröffentlicht - 20 Dez 2018

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Dipole moment
Self assembled monolayers
dipole moments
engineering
electronics
electrostatics
dipoles
Electrostatics
packing density
pyrimidines
contact resistance
thiols
wetting
attachment
Core levels
Molecular orientation
Contact resistance
binding energy
Binding energy
tuning

ASJC Scopus subject areas

  • !!Electronic, Optical and Magnetic Materials
  • !!Energy(all)
  • !!Physical and Theoretical Chemistry
  • !!Surfaces, Coatings and Films

Fields of Expertise

  • Advanced Materials Science

Dies zitieren

Gärtner, M., Sauter, E., Nascimbeni, G., Petritz, A., Wiesner, A., Kind, M., ... Zharnikov, M. (2018). Understanding the Properties of Tailor-Made Self-Assembled Monolayers with Embedded Dipole Moments for Interface Engineering. Journal of Physical Chemistry C, 122(50), 28757-28774. https://doi.org/10.1021/acs.jpcc.8b09440

Understanding the Properties of Tailor-Made Self-Assembled Monolayers with Embedded Dipole Moments for Interface Engineering. / Gärtner, Michael; Sauter, Eric; Nascimbeni, Giulia; Petritz, Andreas; Wiesner, Adrian; Kind, Martin; Abu-Husein, Tarek; Bolte, Michael; Stadlober, Barbara; Zojer, Egbert; Terfort, Andreas; Zharnikov, Michael.

in: Journal of Physical Chemistry C, Jahrgang 122, Nr. 50, 20.12.2018, S. 28757-28774.

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

Gärtner, M, Sauter, E, Nascimbeni, G, Petritz, A, Wiesner, A, Kind, M, Abu-Husein, T, Bolte, M, Stadlober, B, Zojer, E, Terfort, A & Zharnikov, M 2018, 'Understanding the Properties of Tailor-Made Self-Assembled Monolayers with Embedded Dipole Moments for Interface Engineering' Journal of Physical Chemistry C, Jg. 122, Nr. 50, S. 28757-28774. https://doi.org/10.1021/acs.jpcc.8b09440
Gärtner, Michael ; Sauter, Eric ; Nascimbeni, Giulia ; Petritz, Andreas ; Wiesner, Adrian ; Kind, Martin ; Abu-Husein, Tarek ; Bolte, Michael ; Stadlober, Barbara ; Zojer, Egbert ; Terfort, Andreas ; Zharnikov, Michael. / Understanding the Properties of Tailor-Made Self-Assembled Monolayers with Embedded Dipole Moments for Interface Engineering. in: Journal of Physical Chemistry C. 2018 ; Jahrgang 122, Nr. 50. S. 28757-28774.
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