2379-20-6Relevant academic research and scientific papers
Fluorine substituted non-symmetric phenazines: A new synthetic protocol from polyfluorinated azobenzenes
Vaghi, Luca,Coletta, Mattia,Coghi, Paolo,Andreosso, Ivan,Beverina, Luca,Ruffo, Riccardo,Papagni, Antonio
, p. 340 - 351 (2019/09/10)
A high ortho regioselectivity in nucleophilic aromatic substitution in low polar solvents is reported in the reaction of polyfluorinated azobenzenes with anilines. o-Anilino substituted derivatives could be easily transformed into non-symmetric phenazines
Mechanochemical oxidation of fluorinated anilines to symmetric azobenzenes
Andreosso, Ivan,Papagni, Antonio,Vaghi, Luca
, p. 124 - 127 (2018/11/10)
A solventless mechanochemical methodology for the oxidation of electron-poor fluorinated anilines to the corresponding symmetrical azo compounds has been developed. In this process phenyliodine(III)diacetate and inexpensive calcium hypochlorite demonstrat
Electrocatalytic Z → E Isomerization of Azobenzenes
Goulet-Hanssens, Alexis,Utecht, Manuel,Mutruc, Dragos,Titov, Evgenii,Schwarz, Jutta,Grubert, Lutz,Bléger, David,Saalfrank, Peter,Hecht, Stefan
supporting information, p. 335 - 341 (2017/05/16)
A variety of azobenzenes were synthesized to study the behavior of their E and Z isomers upon electrochemical reduction. Our results show that the radical anion of the Z isomer is able to rapidly isomerize to the corresponding E configured counterpart with a dramatically enhanced rate as compared to the neutral species. Due to a subsequent electron transfer from the formed E radical anion to the neutral Z starting material the overall transformation is catalytic in electrons; i.e., a substoichiometric amount of reduced species can isomerize the entire mixture. This pathway greatly increases the efficiency of (photo) switching while also allowing one to reach photostationary state compositions that are not restricted to the spectral separation of the individual azobenzene isomers and their quantum yields. In addition, activating this radical isomerization pathway with photoelectron transfer agents allows us to override the intrinsic properties of an azobenzene species by triggering the reverse isomerization direction (Z → E) by the same wavelength of light, which normally triggers E → Z isomerization. The behavior we report appears to be general, implying that the metastable isomer of a photoswitch can be isomerized to the more stable one catalytically upon reduction, permitting the optimization of azobenzene switching in new as well as indirect ways.
Ortho-Fluoroazobenzenes: Visible Light Switches with Very Long-Lived Z Isomers
Knie, Christopher,Utecht, Manuel,Zhao, Fangli,Kulla, Hannes,Kovalenko, Sergey,Brouwer, Albert M.,Saalfrank, Peter,Hecht, Stefan,Bléger, David
, p. 16492 - 16501 (2016/02/12)
Improving the photochemical properties of molecular photoswitches is crucial for the development of light-responsive systems in materials and life sciences. ortho-Fluoroazobenzenes are a new class of rationally designed photochromic azo compounds with opt
