Science China Chemistry

, Volume 61, Issue 8, pp 909–924 | Cite as

Synthesis and electronic properties of expanded 5-(hetero)aryl-thien-2-yl substituted 3-ethynyl quinoxalines with AIE characteristics

  • Franziska K. Merkt
  • Thomas J. J. MüllerEmail author


Expanded 5-(hetero)aryl-thien-2-yl substituted 3-ethynyl quinoxaline dyes with variable substitution pattern on the peripheral thiophene ring were synthesized in moderate to very good yields by Suzuki and Buchwald-Hartwig coupling of the corresponding brominated 3-ethynyl quinoxalines. Dumbbell-shaped bis(thienyl 3-ethynyl quinoxalines) are also accessible by the Suzuki protocol. The photophysical properties were investigated by UV and fluorescence spectroscopy. Most of the obtained compounds display fluorescence in solution and some of them also in the solid state. Additionally, tuning of the emission color of the quinoxaline based chromophores can be conveniently accomplished by the remote substituent group. The determined absorption and emission maximum as well as the Stokes shifts strongly correlate with Hammett σp+ parameters. Besides, photophysical properties of selected derivatives in the solid state, biphasic solutions, and PMMA films, along with their relationships, are comparatively investigated. Moreover, two 5-(hetero)aryl-thien-2-yl substituted 3-ethynyl quinoxaline dyes are aggregation induced emission (AIE) chromophores indicated by restriction of molecular motions. A covalently restricted 3-ethynyl quinoxaline supports that the inhibition of molecular rotation is responsible for the significant enhancement of fluorescence in acetonitrile/water mixtures.


absorption aggregation induced emission cross-coupling fluorescence heterocycles palladium 


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This work was supported by the Fonds der Chemischen Industrie and Deutsche Forschungsgemeinschaft (Mu 1088/9-1). We cordially thank Tobias Wilcke (Heinrich-Heine-Universität Düsseldorf) for taking the photographs for the graphical abstract.

Supplementary material

11426_2018_9295_MOESM1_ESM.pdf (4.2 mb)
Synthesis and Electronic Properties of Expanded 5-(Hetero)Aryl-Thien-2-yl Substituted 3-Ethynyl Quinoxalines with AIE Characteristics


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Copyright information

© Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Institute of Organic Chemistry and Macromolecular ChemistryHeinrich Heine University DüsseldorfDüsseldorfGermany

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