Stereoselective synthesis of heterocyclic tetraphenylethylene analogues with configuration-dependent solid-state luminescence

Abstract

While ubiquitous in a variety of optoelectronic applications, fluorophores displaying aggregation induced emission (AIE) and in particular those constructed around the tetraphenylethylene (TPE) core suffer severe limitations. In particular, it has been reported on many instances that stereoconfiguration around the central double bond may severely impact the solid-state luminescence properties, i.e., maximal emission wavelength and fluorescence quantum yield. Stereoselective synthesis of extended TPE cores remains challenging, and separation of diastereoisomer mixtures is generally tedious. In this paper, we introduce ditriazolostilbene moities (DTS) as an alternative to TPE. DTS offers two significant advantages over its TPE counterpart: firstly, a fully stereoselective synthesis of the (E)-isomer, and secondly, the use of a copper-catalyzed azide-alkyne cycloaddition (CuAAc) reaction in the final step, which simplifies access to novel derivatives. We illustrate the benefits of this approach using stereopure and (E) and (Z)-aggregates, powders and crystals of the molecule and show that emission properties are considerably dependent on their stereoconfiguration.