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Catechol derivatives as fluorescent chemosensors for wide-range pH detection

AuthorsEvangelio, Emi ; Hernando, Jordi ; Imaz, Inhar ; Alibés, Ramón; Busqué, Félix; Ruiz Molina, Daniel
KeywordspH detection
Fluorescent probes
Issue Date2008
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 14(31): 9754-9763 (2008)
AbstractThe 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 π-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 dualwavelength detection techniques, this compound shows complementary >off-on-off> and >on-off-on> emission profiles upon pH variation, a behavior that can be exploited to perform acidity detection over a broad pH range.
Identifiersdoi: 10.1002/chem.200800722
issn: 0947-6539
e-issn: 1521-3765
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(CIN2) Artículos
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