2,4-Distyryl- and 2,4,6-Tristyrylpyrimidines Synthesis and Photophysical Properties

Michaela Fecková (1, 2) , Pascal Le Poul (1) , Françoise Robin-Le Guen (1) , Thierry Roisnel (1) , Oldřich Pytela (2) , Milan Klikar (2) , Filip Bureš (2) , Sylvain Achelle (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 University of Pardubice

The synthesis of a series of 20 new 2,4,6-tristyrylpyrimidines and three new 2,4-distyrylpyrimidines by means of combination of Knoevenagel condensation and Suzuki-Miyaura cross-coupling reaction is reported. This methodology enables us to obtain chromophores with identical or different substituent on each arm. The photophysical properties of the compounds are described. Optical properties and time-dependent density functional theory calculations indicate that photophysical properties of target compounds are mainly affected by the nature of the electron-donating group in C4/C6 positions, except when the C2 substituent is a significantly stronger electron-donating group. However, the C2 substituent has a strong influence on emission quantum yield addition of a strong electron-donating group tends to decrease the fluorescence quantum yield, whereas a moderate electron-withdrawing group results in a significant increase of fluorescence quantum yield.

Domains: Chemical Sciences; Organic chemistry

Michaela Fecková, Pascal Le Poul, Françoise Robin-Le Guen, Thierry Roisnel, Oldřich Pytela, et al.. 2,4-Distyryl- and 2,4,6-Tristyrylpyrimidines Synthesis and Photophysical Properties. Journal of Organic Chemistry, 2018, 83 (19), pp.11712-11726. ⟨10.1021/acs.joc.8b01653⟩. ⟨hal-01880133⟩