Synthesis of Tetraarylethene Luminogens by C-H Vinylation of Arenes
Compounds showing aggregation-induced emission (AIE) properties have found numerous applications in analytical chemistry, imaging, materials sciences, and biology. Tetraarylethenes are particularly popular in this context. During our investigations of the chemistry of vinyl triazenes,[1-4] we have developed a novel route towards tetraarylethene AIE emitters via metal-free C-H triarylvinylation of aromatic compounds with vinyl triazenes.[5] The scope of the coupling reaction includes simple unactivated arenes, functional arenes, heteroarenes and aromatic polymers. Within the course of this study, we have accidentally found a new class of solid state emitters based on Δ3-triazolines.[6] These molecules display electrofluorochromism: it is possible to convert them reversibly into stable non-fluorescent radical cations.
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[6] A. A. Suleymanov, A. Ruggi, O. M. Planes, A.-S. Chauvin, R. Scopelliti, F. Fadaei-Tirani, A. Sienkiewicz, A. Fabrizio, C. Corminboeuf, K. Severin, Chem. Eur. J. 2019, 25, 6718.