69642-11-1

Upstream product

• 1423-15-0 perfluorophenyl azide 
• 108-88-3 toluene 
• 36375-78-7 pentafluorophenyl nitrene 
• 2285-06-5 (E)-1,2-bis(pentafluorophenyl)diazene 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 

Downstream Products

• 2285-06-5 (E)-1,2-bis(pentafluorophenyl)diazene 

Relevant academic research and scientific papers

Switching the Spin State of Pentafluorophenylnitrene: Isolation of a Singlet Arylnitrene Complex

The chemistry of arylnitrenes is dominated by their triplet ground states and excited open-shell singlet states. This results in radical-type reactions and unwanted rearrangements, which diminish the use of arylnitrenes as intermediates in organic synthes

Electrocatalytic Z → E Isomerization of Azobenzenes

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.

Azo?phenyl stacking: A persistent self-assembly motif guides the assembly of fluorinated cis-azobenzenes into photo-mechanical needle crystals

We describe a novel, persistent motif of molecular assembly in photo-mechanical crystals and cocrystals of fluorinated cis-azobenzenes. The azo?phenyl stacking, preserved upon either chemical substitution or halogen-bonded cocrystallization, guides the assembly of fluorinated cis-azobenzenes into columnar stacks and drives the formation of crystals with needle-like morphologies optimal for photo-mechanical motion.

Ortho-Fluoroazobenzenes: Visible Light Switches with Very Long-Lived Z Isomers

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