Web Release Date: January 9,
Electro- and Photochemical Switching of Dithienylethene Self-Assembled Monolayers on Gold Electrodes
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Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherland and Department of Fuel Cells and Solid State Chemistry, Risoe National Laboratory, Frederiksborgvej 399, P.O. Box 49, DK-4000 Roskilde, Denmark
Received: August 18, 2007
In Final Form: October 17, 2007
Abstract:
The photochemical and electrochemical properties of self-assembled monolayers (SAM) of three structurally distinct hexahydro- and hexafluoro-dithienylcyclopentene-based photochromic switches on gold electrodes are reported. The photochemical and electrochemical switching between the open and closed forms of the dithienylethene SAMs is examined and found to be sensitive to the molecular structure of the switch. For the three dithienylethenes, the electrochemical behavior with respect to electrochemical ring opening/closing is retained in the SAMs. In contrast, a marked dependence on the nature of the anchoring group is observed upon immobilization in terms of the retention of the photochemical properties observed in solution. For the meta-thiophenol anchor both photochemical ring opening and closing are observed in the SAM, while for the thienyl-thiol-anchored switches the photochemically properties are changed markedly compared with those observed in solution. The stability of the monolayers toward desorption following photochemical and electrochemical switching is examined through electrochemistry and X-ray photoelectron spectroscopy.
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