2-Hydroxyazobenzenes to Tailor pH Pulses and Oscillations with Light

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Title2-Hydroxyazobenzenes to Tailor pH Pulses and Oscillations with Light
Publication TypeJournal Article
Year of Publication2010
AuthorsEmond, M, Le Saux T, Maurin S, Baudin JB, Plasson R, Jullien L
JournalChemistry-a European Journal
Volume16
Issue29
Pagination8822-8831
ISBN Number0947-6539
Accession NumberISI:000281060800031
Abstract

This paper evaluates the 2-hydroxyazobenzene 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, H-1 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(3)M(-1)cm(-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.

URL<Go to ISI>://000281060800031
DOI10.1002/chem.201000541
Short Title2-Hydroxyazobenzenes to Tailor pH Pulses and Oscillations with Light
Unit: 
UMR 8640