Publication details

Anodic Deposition of Enantiopure Hexahelicene Layers

Authors

VACEK Jan HRBÁČ Jan STRAŠÁK Tomáš CÍRKVA Vladimír SÝKORA Jan FEKETE Jaroslav POKORNÝ Jan BULÍŘ Jiří HROMADOVÁ Magdalena CRASSOUS Jeanne STORCH Jan

Year of publication 2018
Type Article in Periodical
Magazine / Source ChemElectroChem
MU Faculty or unit

Faculty of Science

Citation
Doi http://dx.doi.org/10.1002/celc.201800565
Keywords electrosynthesis; electronic and spectral properties; helicene; redox chemistry; voltammetry
Description 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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