13162-49-7Relevant academic research and scientific papers
Reversible Redox Switching of Chromophoric Phenylmethylenepyrans by Carbon-Carbon Bond Making/Breaking
Wojcik, Laurianne,Michaud, Fran?ois,Gauthier, Sébastien,Cabon, Nolwenn,Le Poul, Pascal,Gloaguen, Frederic,Le Poul, Nicolas
, p. 12395 - 12405 (2017/12/08)
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 carbon-carbon bond making/breaking. Phenylmethylenepyrans are organic chromophores which are well suited for such purposes 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.
Synthesis of bromo- and carboxylic acid-substituted methylenepyrans
Vologdin, Nikolay,Gauthier, Sebastien,Achelle, Sylvain,Caro, Bertrand,Guen, Francoise Robin-Le
, p. 606 - 614 (2014/07/21)
In this contribution we describe a series of pyranylidene derivatives bearing bromine atoms in various positions. Some of these bromo derivatives have been converted in carboxylic acid by halogen-metal exchange reaction using gaseous CO2 as electrophile. Selected compounds have been studied by UV-visible absorption and cyclic voltametry to study the influence of the substituent on the pyranylidene core.
