title: Four- and Five-Component Syntheses and Photophysical Properties of Emission Solvatochromic 3-Aminovinylquinoxalines.
abstract: 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.
authors.affiliation: Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf , Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
authors.forename: Charlotte F
authors.initials: CF
authors.lastname: Gers-Panther
authors.affiliation: Bundesanstalt für Materialforschung und -prüfung (BAM) , Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany.
authors.forename: Henry
authors.initials: H
authors.lastname: Fischer
authors.affiliation: Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf , Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Nordmann
authors.affiliation: Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf , Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
authors.forename: Theresa
authors.initials: T
authors.lastname: Seiler
authors.affiliation: Bundesanstalt für Materialforschung und -prüfung (BAM) , Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Behnke
authors.affiliation: Bundesanstalt für Materialforschung und -prüfung (BAM) , Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Würth
authors.affiliation: Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf , Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
authors.forename: Walter
authors.initials: W
authors.lastname: Frank
authors.affiliation: Bundesanstalt für Materialforschung und -prüfung (BAM) , Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany.
authors.forename: Ute
authors.identifier: 0000-0002-0944-1115
authors.initials: U
authors.lastname: Resch-Genger
authors.affiliation: Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf , Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
authors.forename: Thomas J J
authors.initials: TJ
authors.lastname: Müller