Publication date: 10th April 2014
Cyclodextrin-Coated Gold Nanoparticles as Platforms for Plasmon-Induced Photoreactions
Noble metal nanostructures such as gold nanoparticles (Au NPs) display a unique optical behavior arising from the resonant excitation of their collective free electron oscillations, the so-called surface plasmon resonance [1]. Electromagnetic field enhancement, generation of energetic charge carriers and local conversion of photon energy into heat are some of the most relevant properties resulting from plasmon excitation, which are currently being exploited in a large variety of applications [2]. Among them, Au NPs have been proposed for the sensitization of organic photoreactions with visible light, which are normally initiated by plasmon-induced photothermal effects and/or charge transfer [3]. Since these processes are highly distance dependent, care has to be taken to ensure maximal approach of the substrate molecules to the nanoparticle surface. For instance, this can be achieved by means of naked, non-coated Au NPs [3]. In this communication we present an alternative strategy towards this aim, which relies on the use of cyclodextrin-coated gold nanoparticles (CD@Au NPs). Exploiting the capacity of cyclodextrins to form inclusion complexes with a wide range of organic compounds as well as their well-known activity as photochemical templates [4], CD@Au NPs are devised to (i) accelerate plasmon-induced photoreactions by inducing the substrate molecules to move in close proximity to the metal surface, and (ii) favor reaction selectivity. As a proof of principle of this approach, in this work we have synthesized thiolated cyclodextrin derivatives, coated gold nanoparticles with them and tested the photocatalytic activity of the resulting assemblies in some benchmark photochemical reactions.
References
[1] Eustis, S.; El-Sayed, M. Chem. Soc. Rev. 2006, 35, 209-217.
[2] Jain, P. K.; Huang, X.; El-Sayed, I. H.; El-Sayed, M. A. Acc. Chem. Res. 2008, 41, 1578-1586.
[3] Scaiano, J. C.; Stamplecoskie, K. J. Phys. Chem. Lett. 2013, 4, 1177-1187.
[4] Svoboda, J.; König, B. Chem. Rev. 2006, 106, 5413-5430.
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