Anodic Deposition of Enantiopure Hexahelicene Layers

Abstract : Helicenes are polyaromatic compounds with chiral properties useful for many applications in optoelectronics, separation processes, chiral recognition and catalysis. Here we focused on the electrochemistry of carbo[n]helicenes (n=5,6,7). The cyclic voltammograms of racemic mixtures of target compounds in acetonitrile/0.1M tetrabutylammonium perchlorate at a glassy carbon electrode reveal the diffusion-controlled reactions in both anodic and cathodic potential regions. Electrochemical behaviors are different for individual helicenes, [7]helicene undergoes redox transformation easily in comparison to the other investigated compounds, which is in agreement with DFT (density functional theory) calculations. Generally, the multi-component anodic process of helicenes is observable at potentials from +1.5 to +2.5V, leading to the formation of deposited structures (layers) on the electrode surface. The helicenes were electrodeposited onto transparent indium tin oxide (ITO) electrodes and characterized by atomic force microscopy, UV/Vis, Raman spectroscopy and ellipsometry. Finally, the anodic deposition of P and M enantiomers of [6]helicene was performed using ITO substrates, resulting in the formation of enantiopure layers of nanometer thicknesses, as confirmed by circular dichroism spectroscopy. The discovered electrosynthetic procedure opens up a new possibility for the immobilization of chiral helicene layers onto solid supports.
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Jan Vacek, Jan Hrbac, Tomas Strasak, Vladimir Cirkva, Jan Sykora, et al.. Anodic Deposition of Enantiopure Hexahelicene Layers. ChemElectroChem, Weinheim : Wiley-VCH, 2018, 5 (15), pp.2080-2088. ⟨10.1002/celc.201800565⟩. ⟨hal-01874560⟩

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