RESUMEN
A simple 4-aniline boron-dipyrromethene (BODIPY) dye (1) was developed as a highly sensitive acidic pH fluorescent probe excitable with visible light based on a photoinduced electron transfer (PeT) mechanism. The pH titration indicates that the fluorescence intensity increases more than 500-fold within the pH range of 4.12-1.42 with a pKa value of 3.24 in methanol-water (1 : 1, v/v) solution, which is valuable for studying strongly acidic conditions. Density functional theory (DFT) calculations reproduce the fluorescence off-on behavior. 1 has also been used as a fluorescent chemosensor for the visual detection of dissolved carbon dioxide (CO2) gas. The underlying mechanism of the sensing process is rationalized. This probe can be recovered by bubbling nitrogen (N2) gas into CO2-treated solutions for over 10 cycles. In addition, two logic gates (OR and INH) have been achieved at the molecular level by changing the initial states of system 1 and chemical inputs.
Asunto(s)
Compuestos de Anilina/química , Compuestos de Boro/química , Dióxido de Carbono/análisis , Colorantes Fluorescentes/síntesis química , Cristalografía por Rayos X , Colorantes Fluorescentes/química , Concentración de Iones de Hidrógeno , Modelos Moleculares , Estructura Molecular , Propiedades de SuperficieRESUMEN
4-Methoxycarbonylphenyl-substituted BODIPY (boron-dipyrromethene) dye gives, in the solid state, three polymorphs. In spite of the absence of any strong intermolecular interactions in all crystalline forms, the three polymorphs show different photoluminescence properties. This behavior highlights the importance of molecular arrangements of the BODIPY moieties in the crystalline state in perturbing their photophysical properties.