Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 31, Pages 9754-9763Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800722
Keywords
catechols; chemosensors; fluorescent probes; pH detection; switches
Categories
Funding
- Ministerio de Educacion v Ciencia (MEC) [MAT2006-13765-C02-01, CTQ2004- 02539, CTQ2006-01040]
- MCyT-ERDF
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The synthesis and characterization of a new family of catechol derivatives designed to behave as fluorescent chemosensors for wide-range pH detection has been described. These compounds were prepared by covalently coupling a catechol unit with other aromatic rings, thus obtaining pi-delocalized systems with both pH-responsive groups and fluorescent behavior. In the case of a pyridine-catechol derivative, this leads to Up to three different protonation states with distinct optical properties in organic media, as corroborated by density functional theory calculations. By applying dual-wavelength detection techniques, this compound shows complementary off- on-off and on-off-on emission profiles upon pH variation, a behavior that call be exploited to perform acidity detection over a broad pH range.
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