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Luminescent Crystalline Carbon‐ and Nitrogen‐Centered Organic Radicals Based on N‐Heterocyclic Carbene‐Triphenylamine Hybrids

Developing luminescent radicals with tunable emission is a challenging task due to the limitation of alternative skeletons. Herein, a series of carbene–triphenylamine hybrids were prepared by the direct C2-arylation of N-heterocyclic carbene with 4-bromo-N,N-bis(4-methoxyphenyl)aniline. These hybrids showed multiple redox-active properties and could be converted to carbon-centered luminescent radicals with blue-to-cyan emissions (λmax: 436–486 nm) or nitrogen-centered luminescent radicals with orange emissions (λmax: 590–623 nm) through chemical reduction or oxidation, respectively. The radical species were characterized by electron paramagnetic resonance spectroscopy, ultraviolet-visible spectroscopy, and single-crystal X-ray diffractometry analysis. Notably, the corresponding nitrogen-centered radicals exhibited good stability in atmospheric air, and their thermal decomposition temperatures were determined to be above 200°C. In addition, spectral and theoretical calculations indicate that all radicals exhibit anti-Kasha emissions

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