ArticleMolecules (Basel, Switzerland)2025
Synthesis and Photophysical Properties of AIE-Type Carbazole-Capped Triphenylmethyl Organic Radicals Featuring Non-Aufbau Electronic Structure and Enhanced Photostability.
Article in Molecules (Basel, Switzerland), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
In this study, we report two novel donor-acceptor (D-A•)-type triphenylmethyl radicals, TTM-1TPE-2Cz and TTM-2TPE-2Cz, synthesized by integrating an aggregation-induced emission (AIE)-active 2-(1, 2, 2-triphenylethenyl)-9H-carbazole (TPE-2Cz) donor with tris(2,4,6-trichlorophenyl)methyl (TTM) radical core. Despite the AIE unit's conventional ACQ-suppressing capability, both radicals exhibit complete emission quenching in solid/solution states but demonstrate 655 nm red emission in polymethyl methacrylate (PMMA)-doped films. Theoretical and experimental analyses reveal that the flexible TPE moiety unexpectedly enhances non-radiative decay while establishing a non-Aufbau electronic configuration through its strong electron-donating nature (-5.16 eV HOMO vs. -5.75 eV SOMO). Remarkably, these radicals achieve unprecedented photostability with half-lives (t₁/₂) 39,000- and 12,000-fold greater than pristine TTM, respectively. This work not only presents a synthetic strategy for stable radicals through non-Aufbau electronic engineering but also elucidates critical structure-property relationships between AIE units and radical photophysics.
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