Details

Autor(en) / Beteiligte

• Schmode, Stella
• Petrosyan, Andranik
• Fennel, Franziska
• Villinger, Alexander
• Lochbrunner, Stefan
• Ludwig, Ralf

Titel

Large Stokes Shift Ionic‐Liquid Dye

Ist Teil von

• Angewandte Chemie International Edition, 2017-07, Vol.56 (29), p.8564-8567

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2017

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• We have incorporated the dye N‐methyl‐6‐oxyquinolone [6MQz] in its protonated form as a cation into an ionic liquid (IL) and thus to synthesize an IL dye. The IL dye N‐methyl‐6‐hydroxyquinolinium bis(trifluoromethylsulfonyl) imide [6MQc][NTf2] was characterized by NMR, ATR IR spectroscopy and X‐ray crystallography. The fluorescence of the IL dye has a large Stokes shift of Δλ=116 nm and a quantum yield of φF=0.56 in acetonitrile. Characteristic solvent dependent shifts can be detected in the emission spectra. In other ILs, acetonitrile and THF we observe a bathochromic shift of up to 28 nm compared to the pure IL dye at 467 nm. For stronger polar solvents the fluorescence signals are strongly red‐shifted to 650 nm indicating proton transfer to the solvent molecules in the excited state. This underlines the importance of the IL building block [MQc]+ as photo acid. Two in one! The dye N‐methyl‐6‐oxyquinolone [6MQz] in its protonated form is incorporated as a cation into an ionic liquid (IL) allowing synthesis of an IL dye. NMR, ATR‐IR, spectroscopy and X‐ray crystallography show that cation and anion are hydrogen bonded in the solid as well as in the liquid state. The IL dye exhibits a large Stokes shift and photo acidity in polar solvents.