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Persistent, Highly Localized, and Tunable [4]Helicene Radicals

preprint
revised on 07.08.2020 and posted on 07.08.2020 by Aslam Shaikh, Jules Moutet, Jose M Veleta, Md Mubarak Hossain, jan bloch, Andrei V. Astashkin, thomas Gianetti

Persistent organic radicals have gained considerable attention in the fields of catalysis and material sciences. In particular, helical molecules are of great interest for the development and application of novel organic radicals in optoelectronic and spintronic materials. Here we report the syntheses of easily tunable and stable neutral quinolinoacridine radicals under anaerobic conditions by chemical reduction of their quinolinoacridinium cation analogs. The structures of these [4]helicene radicals were determined by X-ray crystallography. Density functional theory (DFT) calculations, supported by Electron paramagnetic resonance (EPR) measurements, indicate that over 40% of spin density is located at the central carbon of the [4]helicene radicals regardless of their structural modifications. The localization of the charge promotes a reversible oxidation to the cation upon exposure to air. This unusual reactivity toward molecular oxygen was monitored via UV-Vis spectroscopy.

History

Email Address of Submitting Author

tgianetti@arizona.edu

Institution

University of Arizona

Country

United States

ORCID For Submitting Author

0000-0002-3892-3893

Declaration of Conflict of Interest

no conflict of interest

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