Four- and Five-Component Syntheses and Photophysical Properties of Emission Solvatochromic 3-Aminovinyiquinoxalines

3-Aminovinylquinoxalines are readily accessible from (hetero)aryl glyoxylic acids or heterocyclic pi-nucleophiles by consecutive four- and five component syntheses in the sense of an activation-alkynylation-cyclocondensation-addition sequence or glyoxylation-alkynylation-cydocondensation-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 non radiative fluorescence decay rates in various solvent polarities. The electronic structure is corroborated by DFT and TD-DFT calculations rationalizing the observed spectroscopic effects.