Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf , Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
Bundesanstalt für Materialforschung und -prüfung (BAM) , Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany.
J Org Chem. 2017 Jan 6;82(1):567-578. doi: 10.1021/acs.joc.6b02581. Epub 2016 Dec 28.
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.
3-氨甲酰基喹喔啉可通过（杂）芳基乙醛酸或杂环π-亲核试剂，以连续的四组分和五组分合成方法，按照活化-炔基化-环化-加成序列或糖基化-炔基化-环化-加成序列进行制备，产率良好。标题化合物具有高荧光性，表现出明显的发射溶剂化变色和向红移的荧光猝灭。时间分辨荧光光谱在各种溶剂极性下提供辐射和非辐射荧光衰减速率。电子结构得到了 DFT 和 TD-DFT 计算的支持，合理地解释了观察到的光谱效应。
