ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2023
Conjugation-Induced Spin Delocalization in Helical Chiral Carbon Radicals via Through-Bond and Through-Space Effects.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Article
- Cyclopenta-Fused Polyaromatic Hydrocarbon (CP-PAH) Radicals: Synthesis, Characterization, and Quantum Chemical Calculations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Catalytic kinetic resolution of helical polycyclic phenols via an organocatalyzed enantioselective dearomative amination reaction.Science advances · 2024Article
- Fast photochromism of helicene-bridged imidazole dimers.Chemical science · 2024Article
- Conjugation-Induced Spin Delocalization in Helical Chiral Carbon Radicals via Through-Bond and Through-Space Effects.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
A class of highly stable hydrocarbon radicals with helical chirality are synthesized, which can be isolated and purified by routine column chromatography on silica gel. These carbon-centered radicals are stabilized by through-bond delocalization and intramolecular through-space conjugation, which is evidenced by Density Functional Theory (DFT) calculation. The high stability enables to directly modify the carbon radical via palladium-catalyzed cross-coupling with the radical being untapped. The structures and optoelectronic properties are investigated with a variety of experimental methods, including Electron Paramagnetic Resonance (EPR), Ultraviolet Visisble Near Infrared (UV-vis-NIR) measurements, Cyclic Voltammetry (CV), Thermogravimetry Analysis (TGA), Circular Dichroism (CD) spectra, High-Performance Liquid Chromatography (HPLC), and X-ray crystallographic analysis. DFT calculations indicated that the 9-anthryl helical radical is more stable than its tail-to-tail σ-dimer over 13.2 kJ mol
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Registered trials
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