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2,4-Distyryl- and 2,4,6-Tristyrylpyrimidines: Synthesis and Photophysical Properties
Authors: Fecková Michaela | Le Poul Pascal | Robin-le Guen Francoise | Roisnel Thierry | Pytela Oldřich | Klikar Milan | Bureš Filip | Achelle Sylvain
Year: 2018
Type of publication: článek v odborném periodiku
Name of source: Journal of Organic Chemistry
Publisher name: American Chemical Society
Place: Washington
Page from-to: 11712-11726
Titles:
Language Name Abstract Keywords
cze 2,4-Distyryl- and 2,4,6-tristyrylpyrimidiny: syntéza a fotofyzikální vlastnosti Je popsána syntéza série dvaceti nových 2,4,6-tristyrylpyrimidinů a tří nových 2,4-distyrylpyrimidinů realizovaná kombinací Knoevenagelovy kondenzace a Suzukiho-Miyaurova cross couplingu. Tento postup umožňuje připravit chromofory se stejnými nebo odlišnými substituenty na jednotlivých periferních ramenech molekul. Byly studovány fotofyzikální a optické vlastnosti a prostřednictvím nich popsán vliv jednotlivých skupin vázaných na základní skelet. světloemitující vlastnosti; push-pull chromofory; dvoufotonová absorpce; optické vlastnosti; pyrimidiny; nitroaromatické výbušiny; 1,3,5-triaziny; konjugované materiály; couplingové reakce
eng 2,4-Distyryl- and 2,4,6-Tristyrylpyrimidines: Synthesis and Photophysical Properties 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. light-emitting properties; push-pull chromophores; 2-photon absorption; optical-properties; pyrimidine-derivatives; nitroaromatic explosives; 1,3,5-triazine cores; conjugated materials; octupolar molecules; coupling reactions

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