Photoresponsive SAMs on gold fabricated from azobenzene-functionalised asparagusic acid derivatives

Ulrich Siemeling; Clemens Bruhn; Frauke Bretthauer; Marta Borg; Frank Träger; Florian Vogel; Waleed Azzam; Mihaela Badin; Thomas Strunskus; Christof Wöll

doi:10.1039/B905025F

Photoresponsive SAMs on gold fabricated from azobenzene-functionalised asparagusic acid derivatives†

Ulrich Siemeling,*^ac Clemens Bruhn,^ac Frauke Bretthauer,^ac Marta Borg,^bc Frank Träger,^bc Florian Vogel,^bc Waleed Azzam,‡^d Mihaela Badin,^d Thomas Strunskus §^d and Christof Wöll^d

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^a Institute of Chemistry, University of Kassel, Heinrich-Plett-Str. 40, Germany
E-mail: siemeling@uni-kassel.de

^b Institute of Physics, University of Kassel, Heinrich-Plett-Str. 40, Germany

^c Center for Interdisciplinary Nanostructure Science and Technology, University of Kassel, Heinrich-Plett-Str. 40, Germany

^d Faculty of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstr. 150, Germany

Abstract

We have prepared a range of azobenzene derivatives equipped with an asparagusic acid-based 1,2-dithiolane headgroup suitable for chemisorption on solid gold substrates. The formation of self-assembled monolayers (SAMs) of the amidecyclo-S₂C₃H₅-4-C(O)NH-p-C₆H₄-N [double bond, length as m-dash] N-Ph (1) and the estercyclo-S₂C₃H₅-4-C(O)O-p-C₆H₄-NN-Ph (2) on gold was monitored in situ and in real time by optical second harmonic generation (SHG). The structure and composition of these SAMs was investigated by a range of ex situ methods, viz.ellipsometry, X-ray photoelectron spectroscopy (XPS), near-edge X-ray absorption fine structure (NEXAFS) spectroscopy and Fourier transform infrared reflection absorption spectroscopy (FTIRRAS). Reversible, but moderate, photoswitchability was observed for these one-component SAMs by ellipsometry and dynamic contact angle measurements. Use of a second 1,2-dithiolane component for lateral dilution of the photoactive terminal groups resulted in a much more pronounced photoresponse.

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Photoresponsive SAMs on gold fabricated from azobenzene-functionalised asparagusic acid derivatives†

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Photoresponsive SAMs on gold fabricated from azobenzene-functionalised asparagusic acid derivatives

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