Solution-and solid-state emitters with large Stokes shifts combining pyrene and 4-hydroxythiazole fluorophores. (October 2015)

• Record Type: Journal Article
• Authors: Wrona-Piotrowicz, Anna; Plażuk, Damian; Zakrzewski, Janusz; Métivier, Rémi; Nakatani, Keitaro; Makal, Anna
• Is Part Of: Dyes and pigments. Volume 121(2015)
• Page Start: 290
• Page End: 298
• Publication Date: 2015-10
• Subjects: Pyrene -- 4-Hydroxythiazole -- Fluorescence -- Solid-state -- X-ray structure -- Crystal packing; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2015.05.030
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: 4-Hydroxy-5-nitrophenyl-2-(pyren-1-yl)thiazole and a series of its O -substituted derivatives were synthesised. These compounds are fluorescent in solution, emitting light in the region 598–626 nm with quantum yields 0.19–0.29. Large Stokes shifts, approaching 8500 cm −1, were explained by the intramolecular charge transfer character of the lowest excited state, confirmed by TD DFT calculations. The O -substituted compounds also exhibited fluorescence in the solid state. The lack of solid-state emissive properties of the parent hydroxythiazole and the emission of its O -acetyl derivative are discussed in terms of their crystal packings. Graphical abstract: Highlights: Pyrenyl-substituted "push–pull" 4-R O -thiazoles were synthesized. They exhibits fluorescence in solution at 598–626 nm with quantum yields 0.19–0.29. Large Stokes shifts (up to 8500 cm −1 ) were observed. Solid-state fluorescence at ∼590–640 nm with quantum yields 0.04–0.15 was observed. Time-resolved fluorescence, (TD)DFT and X-ray-diffraction studies were performed.