Improvement of the quadratic non-linear optical properties of pyrimidine chromophores by N-methylation and tungsten pentacarbonyl complexation

Sylvain Achelle (1) , Samia Kahlal (1) , Alberto Barsella (2) , Jean-Yves Saillard (1) , Xiaoyang Che (1) , Julien Vallet (1) , Filip Bureš (3) , Bertrand Caro (1) , Françoise Robin-Le Guen (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 IPCMS - Institut de Physique et Chimie des Matériaux de Strasbourg
3 Institute of Organic Chemistry and Technology [University of Pardubice]

In this contribution, we report the synthesis of two series of compds.: 4-​(arylvinyl)​-​1-​methylpyrimidinium derivs. and tungsten pentacarbonyl complexes of 4-​(arylvinyl)​pyrimidines. Their second order non-​linear properties, measured by Elec.-​Field Induced Second Harmonic generation (EFISH) method, and their photophys. behavior were thoroughly investigated and compared to the corresponding 4-​(arylvinyl)​pyrimidines. A strong enhancement of the NLO response was obsd. upon methylation or complexation by W(CO)​5 of the pyrimidine ring. DFT theor. calcns. were performed to provide complementary insights on the structure-​properties relationships in particular concerning the amplitude of the NLO response.

Domaines: Chimie théorique et/ou physique

Sylvain Achelle, Samia Kahlal, Alberto Barsella, Jean-Yves Saillard, Xiaoyang Che, et al.. Improvement of the quadratic non-linear optical properties of pyrimidine chromophores by N-methylation and tungsten pentacarbonyl complexation. Dyes and Pigments, 2015, 113, pp.562-570. ⟨10.1016/j.dyepig.2014.09.028⟩. ⟨hal-01088697⟩