4-Arylvinyl-2,6-di(pyridin-2-yl)pyrimidines: synthesis and optical properties. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2011

4-Arylvinyl-2,6-di(pyridin-2-yl)pyrimidines: synthesis and optical properties.

Caroline Hadad
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Sylvain Achelle
Joaquín C. García-Martinez
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Julián Rodríguez-López
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Résumé

A series of 4-arylvinyl-2,6-di(pyridin-2-yl)pyrimidines have been efficiently prepared by a double cross-coupling reaction between 2,4-dichloro-6-methylpyrimidine and 2-(tributylstannyl)pyridine, followed by aldol condensation with the appropriate aromatic aldehyde substituted with electron-donating, electron-withdrawing, dendritic, or water-soluble groups. The effect of different protic and aprotic solvents on the optical absorption and emission properties of these systems was studied. Compounds with electron-donating groups display strong emission solvatochromism, suggesting the formation of an intramolecular charge-separated emitting state. The solvatochromic behavior depends not only on the solvent polarity but also on the hydrogen bonding parameters of the solvent. The effect of protonation was also studied, and the abilities of some of these molecules to function as colorimetric and luminescent pH sensors were demonstrated with dramatic color changes and luminescence switching upon the introduction of acid.

Domaines

Chimie organique
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Dates et versions

hal-00875496 , version 1 (22-10-2013)

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Citer

Caroline Hadad, Sylvain Achelle, Joaquín C. García-Martinez, Julián Rodríguez-López. 4-Arylvinyl-2,6-di(pyridin-2-yl)pyrimidines: synthesis and optical properties.. Journal of Organic Chemistry, 2011, 76 (10), pp.3837-45. ⟨10.1021/jo200204u⟩. ⟨hal-00875496⟩
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