139137-46-5Relevant academic research and scientific papers
2-Hydroxyazobenzenes to tailor pH Pulses and oscillations with light
Emond, Matthieu,Saux, Thomas Le,Maurin, Sylvie,Baudin, Jean-Bernard,Plasson, Raphael,Jullien, Ludovic
supporting information; experimental part, p. 8822 - 8831 (2010/11/04)
This paper evaluates the 2hydroxyazobenzene platform for tailoring proton concentration pulses and oscillations with monochromatic light. The easily prepared 2-hydroxyazobenzenes exhibit large absorptions in the near-UV range. Photoisomerization was investigated by UV/Vis absorption, 1H NMR spectroscopy, and steady-state fluorescence emission. In the whole investigated series, the trans stereoisomer of the 2-hydroxyazobenzene motif provides the corresponding cis derivative with an action cross section in the 10 3M-1cm-1 range. At the same time, photoisomerization is accompanied by a significant pK drop of the phenol group. According to the phenyl-substituent pattern, cis-to-trans thermal back-isomerization can be tuned in the 10 ms-100 s range. Up to 2 units of reversible pH drops or pH oscillations on the 10 s timescale have been obtained by appropriately tailoring single-wavelength illumination of 2-hydroxyazobenzene solutions.
