Self-assembled monolayers of perfluoroanthracenylaminoalkane thiolates on gold as potential electron injection layers

• Verfasst von: Zhang, Zibin [VerfasserIn]
• Verfasst von: Wächter, Tobias [VerfasserIn]
• Verfasst von: Kind, Martin [VerfasserIn]
• Verfasst von: Schuster, Swen [VerfasserIn]
• Verfasst von: Bats, Jan W. [VerfasserIn]
• Verfasst von: Nefedov, Alexei [VerfasserIn]
• Verfasst von: Zharnikov, Michael [VerfasserIn]
• Verfasst von: Terfort, Andreas [VerfasserIn]
• Titel: Self-assembled monolayers of perfluoroanthracenylaminoalkane thiolates on gold as potential electron injection layers
• Verf.angabe: Zibin Zhang, Tobias Wächter, Martin Kind, Swen Schuster, Jan W. Bats, Alexei Nefedov, Michael Zharnikov, and Andreas Terfort
• E-Jahr: 2016
• Jahr: 9 March 2016
• Umfang: 9 S.
• Teil: volume:8
• Teil: year:2016
• Teil: number:11
• Teil: pages:7308-7319
• Teil: extent:9
• Fussnoten: Gesehen am 08.10.2021
• Titel Quelle: Enthalten in: American Chemical SocietyACS applied materials & interfaces
• Ort Quelle: Washington, DC : Soc., 2009
• Jahr Quelle: 2016
• Band/Heft Quelle: 8(2016), 11, Seite 7308-7319
• ISSN Quelle: 1944-8252
• DOI: doi:10.1021/acsami.6b00532
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1772811874

Abstract

As a material with relatively small band gap and low lying valence orbitals, perfluoroanthracene (PFA) is of interest for the modification of electrode surfaces, for example, as charge injection layers for n-type organic semiconductors. To covalently attach PFA in the form of self-assembled monolayers (SAMs), we developed a synthesis of derivatives with a sulfur termination, linked to the 2-position of the PFA moieties by an −NH- group and a short alkane chain with two and three methylene groups, respectively. Spectroscopic characterization of the SAMs reveals that the molecules adopt an almost upright orientation on the gold surface, with the packing density mostly determined by the steric demands of the PFA units. The number of the methylene groups in the −NH-alkyl linker has only a minor impact on the SAM structure because of the nonsymmetric attachment of the PFA units, which permits the compensation of the orientational constraints imposed by the bending potential. The investigated SAMs alter the work function of gold by +(0.59-0.64) eV, suggesting comparably strong depolarization effects, affecting the extent of the work function modification.