Journal of Organic Chemistry 2012-04-20

Synthesis and photophysical investigation of a series of push-pull arylvinyldiazine chromophores.

Sylvain Achelle, Alberto Barsella, Christine Baudequin, Bertrand Caro, Françoise Robin-le Guen

Index: J. Org. Chem. 8th ed., 77 , 4087-4096, (2012)

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Abstract

A new series of push-pull arylvinyldiazines has been efficiently prepared by aldol condensation between the appropriate methyldiazine and aromatic aldehyde. The optical absorption and emission properties of these chromophores were studied in different solvents and media. These compounds act as polarity sensors with a strong positive emission solvatochromism. This behavior suggests a highly polar emitting state, which is characteristic of compounds that undergo an internal charge transfer upon excitation. These molecules also exhibit halochromic properties and are potential colorimetric and luminescence pH sensors. The second-order nonlinear properties have been investigated for some of the compounds, and large and positive μβ are obtained, in particular, for pyrimidine derivatives.© 2012 American Chemical Society