AVS 62nd International Symposium & Exhibition
    Thin Film Monday Sessions
       Session TF+AS+SS-MoM

Paper TF+AS+SS-MoM11
Symmetric Attachment of Annulated Aromatic Hydrocarbons in Self-assembled Monolayers by Use of Oxazoles

Monday, October 19, 2015, 11:40 am, Room 111

Session: Self-Assembled Monolayers, Layer-by-Layer, etc.
Presenter: Martin Kind, University of Frankfurt, Germany
Authors: C. Partes, University of Frankfurt, Germany
S. Schuster, University of Heidelberg, Germany
T. Wächter, University of Heidelberg, Germany
M. Kind, University of Frankfurt, Germany
M. Zharnikov, University of Heidelberg, Germany
A. Terfort, University of Frankfurt, Germany
Correspondent: Click to Email
Self-assembled monolayers (SAMs) have proven to be powerful tools for tuning surface properties because of the uncomplicated method of their preparation and the high variability of their organic moieties. The suitability of SAMs in applications like, e.g., organic electronics is frequently investigated. An aim for the use of SAMs is the reduction of injection barriers that occur at the interfaces between organic semiconductors and technologically relevant substrates like gold or silicon.

A SAM ideal for this purpose should exhibit a high vertical conductivity. In view of this, we investigated several aromatic and araliphatic SAMs, e.g. terphenyl-terminated monolayers on gold [1]. In a more recent ansatz, we have examined SAMs bearing annulated moieties such as anthracene, which in contrast to oligophenyls are entirely planar [2]. However, as a consequence of the asymmetric substitution of anthracene to the thiol anchor group it is hardly possible to alter the tilt angle of these thiolate molecules within the SAMs [2].

To overcome this drawback, we extended the annulated system of the SAM-forming thiols with an oxazole unit, which allows for a quasi-symmetric attachment to the ancor group. This restores the possibility to influence the tilt angle of the aromatic units using the so-called odd-even effect in SAMs.

Here, we like to present preliminary results on preparation and structural properties of SAMs made from aromatic oxazole thiols on gold surfaces.

REFERENCES

[1] Shaporenko, A.; Brunnbauer, M.; Terfort, A.; Grunze, M.; Zharnikov, M./J. Phys. Chem. B/108, 14462-14469 (2004).

[2] Dauselt, J.; Zhao, J.; Kind, M.; Binder, R.; Bashir, A.; Terfort, A.; Zharnikov, M./ J. Phys. Chem. C/115, 2841-2854 (2011).