| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 175366 | Dyes and Pigments | 2016 | 10 Pages |
•Indoles were prepared by one-pot Sonogashira coupling and fluoride promoted cyclization.•Intense fluorescence in solution in polar and non-polar solvents was observed.•Compounds showed solvatofluorochromism.
Nine novel 2-aryl-6-(aryleneethynylene)-1H-indoles were prepared by one pot Sonogashira cross-coupling in DMSO and fluoride promoted cyclization followed by N-alkylation. The photophysical properties of these compounds are described. Absorption and excitation spectra of these compounds were independent of the solvent polarity, while their emission spectra showed a pronounced dependence. Fluorescence quantum yields in solution were very high and decreased with solvent polarity; possible processes that account for excessive values of ϕ are discussed. Cyclic voltammetry studies indicate irreversible redox processes and DFT calculations suggest they occur in the indole segment.
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