Three-Component Synthesis and Photophysical Properties of Novel Coumarin-Based Merocyanines.

Autor: Papadopoulos, Julian, Merkens, Kay, Meller, Thomas J. J.
Předmět:
Zdroj: Chemistry - A European Journal; 1/19/2018, Vol. 24 Issue 4, p974-983, 10p
Abstrakt: Novel E-configured coumarin-based merocyanines were efficiently synthesized by a one-pot, three-component Sonogashira coupling-Michael addition starting from triflyl coumarins, terminal alkynes and secondary amines. The photophysical properties of the synthesized yellow to orange merocyanines were studied by UV/Vis and fluorescence spectroscopy and rationalized by Hammett-Taft correlations and DFT and TD-DFT calculations. Most compounds were only weakly fluorescent in solution; however, two compounds were investigated in more detail with respect to their aggregation behavior. The system for R2=H and NR2 3= pyrrolidinyl shows aggregation induced emission at a water content of 40-60% in methanol, while the chromophore with R2=p-Me2NC6H4 and NR2 3=morpholinyl displays considerable aggregation induced emission enhancement with a concomitant redshift at increasing water contents in THF. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index