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Solution-and solid-state emitters with large Stokes shifts combining pyrene and 4-hydroxythiazole fluorophores

Wrona-Piotrowicz, A; Plazuk, D; Zakrzewski, J; Metivier, R; Nakatani, K; Makal, A DYES AND PIGMENTS 2015, 121, 290-298.

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.

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Publication

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Paru le 1 juin 2015

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DOI: 10.1016/j.dyepig.2015.05.030