期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 29, 页码 8822-8831出版社
WILEY-BLACKWELL
DOI: 10.1002/chem.201000541
关键词
acidity; azo compounds; isomerization; photochromism; protonation
资金
- Nordita
- Pierre-Gilles de Gennes Foundation
- European program COST [CM0703]
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, (1)H 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.
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