2-Arylvinylpyrimidines versus 4-arylvinylpyrimidines: synthesis and comparison of the optical properties. - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Tetrahedron Letters Année : 2013

2-Arylvinylpyrimidines versus 4-arylvinylpyrimidines: synthesis and comparison of the optical properties.

Résumé

Condensation of donor-substituted aldehydes on methylpyrimidine led to two series of fluorescent molecules depending on the position of the methyl group. Whereas highly emissive 4-arylvinylpyrimidine derivatives are well-known, this is the first example of fluorescent 2-arylvinylpyrimidine compounds. The optical properties of the two families have been thoroughly compared. Whereas the series derived from 2-methylpyrimidine exhibit a blue shift in absorption and emission in comparison with 4-arylvinylpyrimidine, the influence of the position is less predictable on the fluorescence quantum yield. These compounds also exhibit halochromism: when adding acid, a bathotromic shift is observed in absorption whereas an increase of the fluorescence intensity which is red-shifted except for amino derivatives (a progressive quench of emission is observed in these cases). An emission solvatochromism study has shown that a higher intramolecular charge transfer seems to occur in 2-arylvinylpyrimidines than in 4-arylvinylpyrimidines.

Domaines

Chimie organique
Fichier principal
Vignette du fichier
Arylvinylpyrimidines.pdf (652.55 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)
Loading...

Dates et versions

hal-00915008 , version 1 (06-12-2013)

Identifiants

Citer

Sylvain Achelle, Françoise Robin-Le Guen. 2-Arylvinylpyrimidines versus 4-arylvinylpyrimidines: synthesis and comparison of the optical properties.. Tetrahedron Letters, 2013, 54 (33), pp.4491-4496. ⟨10.1016/j.tetlet.2013.06.040⟩. ⟨hal-00915008⟩
86 Consultations
256 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More