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Using Photoactive N-Heterocyclic Carbenes Monolayers to Identify the Influence of Surface Proximity on Photoswitching Activity

preprint
submitted on 27.10.2020, 13:28 and posted on 29.10.2020, 12:48 by Shahar Dery, Israel Alshanski, Evgeniy Mervinetsky, Daniel Feferman, Shlomo Yitzchaik, Mattan Hurevich, Elad Gross

Self-assembly of photoresponsive molecules is a robust technology for reversibly tuning the chemical and electronic properties of functional materials. In most systems the photoactive group is separated from the surface by a spacer and thus the photo-responsiveness does not benefit from interactions with the metal. Herein, the impact of metal photoactive-group interactions on photoswitchability and surface potential were probed by self-assembly of N-heterocyclic carbene molecules (NHCs) that were functionalized with stilbene group directly on their imidazole ring. Stilbene-NHCs that were adsorbed on weakly interacting Au surface accumulated a vertical orientation, as identified by FTIR measurements. This positioning enabled structural flexibility and high photoisomerization efficiency that induced reversible changes in surface potential. Stilbene-NHCs that were anchored on Pt film accumulated flat-lying adsorption geometry due to strong metal-adsorbate interactions. These interactions limited the structural flexibility of the stilbene groups and induced deteriorated photoswitchability that led to lower photoinduced changes in surface potential. While stronger metal-adsorbate interactions hindered the photo-induced isomerization yield of stilbene, these interactions prompted the cis-to-trans thermal-induced isomerization rate, which was an order of magnitude higher on Pt than on Au.

Funding

ERC StG (Grant Agreement No. 802769,“MapCat”)

History

Email Address of Submitting Author

elad.gross@mail.huji.ac.il

Institution

Hebrew University

Country

Israel

ORCID For Submitting Author

0000-0002-8330-7299

Declaration of Conflict of Interest

No conflict of interests

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