Improvement of the quadratic non-linear optical properties of pyrimidine chromophores by N-methylation and tungsten pentacarbonyl complexation. (February 2015)

• Record Type: Journal Article
• Authors: Achelle, Sylvain; Kahlal, Samia; Barsella, Alberto; Saillard, Jean-Yves; Che, Xiaoyang; Vallet, Julien; Bureš, Filip; Caro, Bertrand; Guen, Françoise Robin-le
• Is Part Of: Dyes and pigments. Volume 113(2015)
• Page Start: 562
• Page End: 570
• Publication Date: 2015-02
• Subjects: Pyrimidine -- Internal charge transfer -- Push–pull chromophores -- Tungsten pentacarbonyl complexes -- Non-linear optics -- Theoretical calculations; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2014.09.028
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: In this contribution, we report the synthesis of two series of compounds: 4-(arylvinyl)-1-methylpyrimidinium derivatives and tungsten pentacarbonyl complexes of 4-(arylvinyl)pyrimidines. Their second order non-linear properties, measured by Electric-Field Induced Second Harmonic generation (EFISH) method, and their photophysical behavior were thoroughly investigated and compared to the corresponding 4-(arylvinyl)pyrimidines. A strong enhancement of the NLO response was observed upon methylation or complexation by W(CO)5 of the pyrimidine ring. DFT theoretical calculations were performed to provide complementary insights on the structure-properties relationships in particular concerning the amplitude of the NLO response. Highlights: N -Methylation and complexation by W(CO)5 of 4-(arylvinyl)pyrimidine were described. A strong Internal Charge Transfer is observed for all the compounds. Strong enhancement of the second order NLO response was observed upon methylation. DFT calculations were performed on these series of compounds.