Persistent, highly localized, and tunable [4]helicene radicals

Aslam C. Shaikh, Jules Moutet, José M. Veleta, Md Mubarak Hossain, Jan Bloch, Andrei V. Astashkin, Thomas L. Gianetti

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Persistent organic radicals have gained considerable attention in the fields of catalysis and materials science. 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 our [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.

Original languageEnglish (US)
Pages (from-to)11060-11067
Number of pages8
JournalChemical Science
Volume11
Issue number40
DOIs
StatePublished - Oct 28 2020

ASJC Scopus subject areas

  • Chemistry(all)

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