New luminescent compounds based on the 4-arylidene-5(4H)-thiazolone scaffolds

Abstract

The synthesis of compounds with strong luminescent properties is a very active research field due to the large variety of industrial applications (OLEDs, biochemical probes, etc.). Up to date, only a restricted collection of such molecules is available. Among these, 4-arylidene-5(4H)-oxazolones and imidazolones (called GFP-like fluorophores) have shown promising luminescent properties. In this context, we report herein the synthesis and structural characterization of new 4-arylidene-5(4H)-thiazolone starting from their 4-arylidene-5(4H)-oxazolones analogues. To increase the luminescence efficiency palladium(II) was incorporated into the molecular scaffold of thiazolone by C-H bond activation. All the new thiazolone and the corresponding organopalladium(II) complexes were characterized by solution NMR spectroscopy (1H, 13C, 19F, 2D) and mass spectrometry. For representative compounds the molecular structure was established by single-crystal X-Ray diffraction. The optical properties of thecomplexes were investigated by luminescent measurements.