Journalartikel

Jahr der Veröffentlichung: 2024

Zeitschrift: European Journal of Organic Chemistry

Bandnummer: 27

Heftnummer: 26

ISSN: 1434-193X

eISSN: 1099-0690

Open Access Status: Hybrid

DOI Link: https://doi.org/10.1002/ejoc.202400298

Verlag: Wiley

Abstract: 
Imidazo[1,5-a]quinolines emit intense blue luminescence, suggesting their possible use as emitter molecules in organic light-emitting diodes. We synthesized several new imidazo[5,1-a]isoquinolines and found they possessed a characteristic hypsochromic effect and even increased quantum efficiency compared to the homolog imidazo[1,5-a]quinolines, as measured by UV-vis- and fluorescence spectroscopy in solution. The energies of the highest occupied and lowest unoccupied molecular orbitals were calculated using density functional theory and experimentally determined by cyclic voltammetry in solution. We obtained a maximum fluorescence quantum yield of 48 % at 446 nm for the newly synthesized 3-(4-cyanophenyl)-1-(pyridyl)imidazo[5,1-a]isoquinoline with an optimized substitution pattern. For 1-phenyl-3-(2-pyridinyl)imidazo[5,1-a]isoquinoline, a quantum yield of 33 % was obtained at an even shorter emission wavelength of 431 nm.

Harvard-Zitierstil: Rössiger, C., Oel, T., Schweitzer, P., Vasylets, O., Kirchner, M., Abdullahu, A., et al. (2024) Synthesis and Optical and Theoretical Characterization of Imidazo[5,1-a]isoquinolines and Imidazo[1,5-a]quinolines, European Journal of Organic Chemistry, 27(26), Article e202400298. https://doi.org/10.1002/ejoc.202400298

APA-Zitierstil: Rössiger, C., Oel, T., Schweitzer, P., Vasylets, O., Kirchner, M., Abdullahu, A., Schlettwein, D., & Göttlich, R. (2024). Synthesis and Optical and Theoretical Characterization of Imidazo[5,1-a]isoquinolines and Imidazo[1,5-a]quinolines. European Journal of Organic Chemistry. 27(26), Article e202400298. https://doi.org/10.1002/ejoc.202400298