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Updated: May 20, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Diverse Postfunctionalization of Open-Shell Diradicaloids and Impact of Conjugated Functional Substituents on
Wang Xiao1, Lei Tian1, Xuejiao Wu1
1State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
Abstract:
Organic radicals are usually incapable of postfunctionalization for structure expansion and optoelectronic property optimizations. Herein, based on a sulfone-embedded skeleton derived from Chichibabin's hydrocarbon, we showcase the regioselective bromination and further postmodifications of open-shell diradicaloids via diverse palladium-catalyzed nucleophilic substitution, Sonogashira coupling, and Stille coupling reactions. Such facile structural expansions yielded a series of conjugated singlet diradicaloids, showing finely tuned physicochemical characteristics, versatile crystalline-state molecular configurations and packing modes, and impressive charge-carrier mobility of 1.5 cm2/V·s.
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