Premium
Catechol Derivatives as Fluorescent Chemosensors for Wide‐Range pH Detection
Author(s) -
Evangelio Emilia,
Hernando Jordi,
Imaz Inhar,
Bardají Gisela G.,
Alibés Ramon,
Busqué Félix,
RuizMolina Daniel
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800722
Subject(s) - catechol , fluorescence , delocalized electron , chemistry , protonation , photochemistry , derivative (finance) , covalent bond , pyridine , combinatorial chemistry , organic chemistry , ion , physics , quantum mechanics , financial economics , economics
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 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 dual‐wavelength 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.