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

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• 作者：Charlotte F. Gers-Panther ; Henry Fischer ; Jan Nordmann ; Theresa Seiler ; Thomas Behnke ; Christian Würth ; Walter Frank ; Ute Resch-GengerThomas J. J. Müller
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：82
• 期：1
• 页码：567-578
• 全文大小：727K
• ISSN：1520-6904

文摘

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.