Skip to Main content Skip to Navigation
Journal articles

Reversible redox switching of chromophoric phenylmethylenepyrans by carbon-carbon bond making/breaking

Abstract : Electrochromic organic systems that can undergo substantial variation of their optical properties upon electron stimulus are of high interest for the development of functional materials. In particular, devices based on radical dimerization are appropriate because of the effectiveness and speed of the carbon-carbon bond making/breaking. Phenylmethylenepyrans are organic chromophores which are well suited for such purpose since their oxidation leads to the reversible formation of bispyrylium species by radical dimerization. In this paper, we show that the redox and spectroscopic properties of phenylmethylenepyrans can be modulated by adequate variation of the substituting group on the para position of the phenyl moiety, as supported by DFT calculations. This redox switching is reversible over several cycles and is accompanied by a significant modification of the UV-Vis spectrum of the chromophore, as shown by time-resolved spectroelectrochemistry in thin layer conditions.
Document type :
Journal articles
Complete list of metadatas

Cited literature [8 references]  Display  Hide  Download

https://hal.univ-brest.fr/hal-01624342
Contributor : Frederic Gloaguen <>
Submitted on : Wednesday, January 10, 2018 - 12:47:09 PM
Last modification on : Friday, October 23, 2020 - 4:35:55 PM
Long-term archiving on: : Friday, May 4, 2018 - 1:48:13 PM

File

Wojcik et al. - 2017 - Reversi...
Files produced by the author(s)

Identifiers

Citation

Laurianne Wojcik, François Michaud, Sebastien Gauthier, Nolwenn Cabon, Pascal Le Poul, et al.. Reversible redox switching of chromophoric phenylmethylenepyrans by carbon-carbon bond making/breaking. Journal of Organic Chemistry, American Chemical Society, 2017, 82 (23), pp.12395 - 12405. ⟨10.1021/acs.joc.7b02199⟩. ⟨hal-01624342⟩

Share

Metrics

Record views

505

Files downloads

352