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

被引：36

作者：

Gers-Panther, Charlotte F. ^{[1
]}

Fischer, Henry ^{[2
]}

Nordmann, Jan ^{[1
]}

Seiler, Theresa ^{[1
]}

Behnke, Thomas ^{[2
]}

Wuerth, Christian ^{[2
]}

Frank, Walter ^{[3
]}

Resch-Genger, Ute ^{[2
]}

Mueller, Thomas J. J. ^{[1
]}

机构：

[1] Heinrich Heine Univ Dusseldorf, Inst Organ Chem & Makromol Chem, Univ Str 1, D-40225 Dusseldorf, Germany

[2] Bundesanstalt Mat Forsch & Prufung BAM, Richard Willstatter Str 11, D-12489 Berlin, Germany

[3] Heinrich Heine Univ Dusseldorf, Inst Anorgan Chem & Strukturchem, Univ Str 1, D-40225 Dusseldorf, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 01期

关键词：

NONEQUILIBRIUM SOLVATION; MULTICOMPONENT REACTIONS; ORGANIC SENSITIZERS; PI-A; QUINOXALINES; ENERGY; ABSORPTION; FIELD; CYCLIZATION; ACTIVATION;

D O I：

10.1021/acs.joc.6b02581

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：567 / 578

页数：12

共 89 条

[81] Assessment of a long-range corrected hybrid functional [J].