Catechol derivatives as fluorescent chemosensors for wide-range pH detection.
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 can be exploited to perform acidity detection over a broad pH range.
Evangelio
Emilia
E
Institut de Ciència de Materials de Barcelona (CSIC), Esfera UAB, 08193, Cerdanyola del Vallès (Spain).
Hernando
Jordi
J
Imaz
Inhar
I
Bardají
Gisela G
GG
Alibés
Ramon
R
Busqué
Félix
F
Ruiz-Molina
Daniel
D