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Self-Assembled Layers of Functionalized Nitrosobenzenes on Gold

Self-assembled monolayers (SAMs) of organic compounds have been extensively investigated over the past two decades for potential applications in areas ranging from molecular-based electronics and optical devices to biorecognition sensors. In recent years there has been a growing interest in preparing SAMs with increasing complexity and diverse functionality. Nitrosobenzenes are very interesting materials because of photochromic and thermochromic effects they produce in the solid state due to nitroso monomer-dimer equilibrium. Incorporation of such a “ chemical switch” , by which it is possible to break the chemical bond between two nitrogen atoms and bind them again, into SAM architectures could lead to intriguing nanosystems. In order to achieve formation of SAMs on gold substrates, aromatic nitroso compounds were functionalized with disulfide end group which specifically binds to gold. Once adsorbed to the surface, molecules organize themselves laterally through van der Waals interactions between aliphatic backbone, π -π interactions between aromatic backbone and terminal group interactions (in our case – N=O group interactions). The structure of the resulting thin film of a functionalized nitrosobenzene assembled on gold was examined by means of scanning tunneling microscopy (STM) and atomic force microscopy (AFM). Formation of dimeric nitrosobenzene domains (RON=NOR) on gold surface will be discussed.

self-assembly ; nitrosobenzene ; gold ; AFM ; STM ; dimers

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