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Issue 15, 2014
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Light-induced reversible modification of the work function of a new perfluorinated biphenyl azobenzene chemisorbed on Au (111)

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Abstract

We describe the synthesis of a novel biphenyl azobenzene derivative exhibiting: (i) a protected thiol anchoring group in the α-position to readily form self-assembled monolayers (SAMs) on Au surfaces; and (ii) a terminal perfluorinated benzene ring in the ω-position to modify the surface properties. The design of this molecule ensured both an efficient in situ photoswitching between the trans and cis isomers when chemisorbed on Au(111), due to the presence of a biphenyl bridge between the thiol protected anchoring group and the azo dye, and a significant variation of the work function of the SAM in the two isomeric states, induced by the perfluorinated phenyl head group. By exploiting the light responsive nature of the chemisorbed molecules, it is possible to dynamically modify in situ the work function of the SAM-covered electrode, as demonstrated both experimentally and by quantum-chemical calculations, revealing changes in work function up to 220 meV. These findings are relevant for tuning the work function of metallic electrodes, and hence to dynamically modulate charge injection at metal–semiconductor interfaces for organic opto-electronic applications.

Graphical abstract: Light-induced reversible modification of the work function of a new perfluorinated biphenyl azobenzene chemisorbed on Au (111)

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Publication details

The article was received on 07 Apr 2014, accepted on 05 Jun 2014 and first published on 11 Jun 2014


Article type: Paper
DOI: 10.1039/C4NR01880J
Citation: Nanoscale, 2014,6, 8969-8977
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    Light-induced reversible modification of the work function of a new perfluorinated biphenyl azobenzene chemisorbed on Au (111)

    A. M. Masillamani, S. Osella, A. Liscio, O. Fenwick, F. Reinders, M. Mayor, V. Palermo, J. Cornil and P. Samorì, Nanoscale, 2014, 6, 8969
    DOI: 10.1039/C4NR01880J

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