Highly Substituted Δ³‐1,2,3‐Triazolines: Solid‐State Emitters with Electrofluorochromic Behavior

Abstract

Highly substituted D 3 -1,2,3-triazolines can be prepared by reactiono ft riarylvinyl Grignardr eagents with functionalized organic azides.The heterocycles are fluorescent in the solid state, and-dependingo nt he substituents-they can display aggregation-induced emission. Upon oxidation, the triazolinesf orm stable radical cations with alteredp hotophysical properties. Therefore, they represent rare examples of solid-state emittersw ith intrinsic electrofluorochromic behavior.

Fluorinated Tetraarylethenes: Universal Tags for the Synthesis of Solid State Luminogens

“…It is worth noting that thianthrenes are known to form stable radical cations [27] . Therefore, 27 and 28 might find applications as redox‐switchable AIE luminogens [28] . For the reaction of 1 with catechol, we also obtained a double substitution product, 29 , which could be isolated in 33 % yield.…”

Survey of Recent Advances in Molecular Fluorophores, Unconjugated Polymers, and Emerging Functional Materials Designed for Electrofluorochromic Use

“…Other nitrogen-containing aromatics that are ideal electrofluorochromes because of their inherent electroactivity and moderate fluorescence are triazolines. A. Suleymanov et al examined several polysubstituted triazoline derivatives with respect to their electrofluorochromism [ 89 ]. While their triazolines did not fluoresce in solution, the solid-state Φ fl values of F3 and F4 were ca.…”

Synthesis of Indenyl Triazenes by Rhodium‐Catalyzed Annulation Reactions

“…We have recently published a modified version of the Grignard/azide route, which involves an intramolecular alkylation step . This procedure has a broader scope, but limitations were still encountered . Instead of azides, it is possible to use aminodiazotates for the coupling with vinyl Grignard reagents, but only few examples have been reported so far .…”