Four- and Five-Component Syntheses and Photophysical Properties of Emission Solvatochromic 3-Aminovinylquinoxalines
2017
Gers-Panther, Charlotte F. | Fischer, Henry | Nordmann, Jan | Seiler, Theresa | Behnke, Thomas | Würth, Christian | Frank, Walter | Resch-Genger, Ute | Müller, Thomas J. J.
3-Aminovinylquinoxalines are readily accessible from (hetero)aryl glyoxylic acids or heterocyclic π-nucleophiles by consecutive four- and five-component syntheses in the sense of an activation-alkynylation-cyclocondensation-addition sequence or glyoxylation-alkynylation-cyclocondensation-addition sequence in good yields. The title compounds are highly fluorescent with pronounced emission solvatochromicity and protochromic fluorescence quenching. Time-resolved fluorescence spectroscopy furnishes radiative and nonradiative fluorescence decay rates in various solvent polarities. The electronic structure is corroborated by DFT and TD-DFT calculations rationalizing the observed spectroscopic effects.
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