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Methylenepyran based dipolar and quadrupolar dyes: synthesis, electrochemical and photochemical properties

Abstract : This paper presents the synthesis of a series of push-pull and quadrupolar π-conjugated structures incorporating pro-aromatic methylenepyran electron-donor groups and various electron-attracting groups. Some of the methylenepyran derivatives were oxidized by I2 to give, after reduction by Na2S2O3, bismethylenepyran compounds via successive steps. The electrochemical redox properties of methylenepyrans 5-9 and extended bismethylenepyrans 10, 14, and 15 determined by cyclic voltammetry indicate the formation of redox bistable systems with high bi-stability. Oxidation of the dimers obtained from 5 to 9 was also described. All compounds are colored and slightly fluorescent (except some bismethylenepyran derivatives). Some compound second-order nonlinear optical properties were investigated, and large positive values of μβ were obtained. A positive dimer effect was also observed for bispyran derivatives.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01059431
Contributor : Sylvain Achelle <>
Submitted on : Sunday, August 31, 2014 - 10:05:27 PM
Last modification on : Friday, July 10, 2020 - 4:05:40 PM

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Sébastien Gauthier, Nikolay V. Vologdin, Sylvain Achelle, A. Barsella, Bertrand Caro, et al.. Methylenepyran based dipolar and quadrupolar dyes: synthesis, electrochemical and photochemical properties. Tetrahedron, Elsevier, 2013, 69, pp.8392. ⟨10.1016/j.tet.2013.07.066⟩. ⟨hal-01059431⟩

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