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NEW WATER SOLUBLE BODIPY DYES THROUGH SIMPLE FUNCTIONALIZATION IN BORON
ES2923998
The known hydrophobicity of BODIPYs and their most common analogues is an important limitation on their optimal use in some applications that require solubility in water. Therefore, the access to BODIPYs that show solubility in water or in highly hydrophilic media from conventional precursor BODIPYs is a matter of interest. The invention refers to the structural design, synthetic access and water solubility of a new group of hydrophilic molecular dyes within the BODIPY family. As an advantage, these BODIPYs are obtained from conventional BODIPY dyes (based on F-BODIPY) through a general and easy procedure, which entails the minimum perturbation of the photophysical properties of the starting dye. Additionally, the new BODIPY dyes have significant chemical and photophysical robustness, allowing their potential use in photonic, physical and chemical applications in aqueous or highly hydrophilic media.
ADVANTAGES: The advantages provided by the invention with respect to the state of the art in the field of obtaining water soluble BODIPY dyes, namely: 1. Its generality. 2. Its chemical simplicity, as it does not require severe reaction conditions, or organometallic reagents, or high substrate/reagent stoichiometric ratios to achieve the functionalization of the boron atom of the starting dye. 3. The fact that the obtained hydrophilic BODIPY dyes functionalized at boron have photophysical properties similar to those of the starting lipophilic dye and also high chemical and photophysical robustness, as they are based on COO-BODIPY. APPLICATIONS: For the achievement of: 1. Hydrophilic fluorescent labels for microscopy 2. Water-soluble agents for intravenous photodynamic therapy 3. Water-soluble agents for photodynamic antimicrobial treatment (microbial inactivation) 4. Water-soluble contrast agents for medical diagnosis 5. Laser dyes that can be used in aqueous or highly hydrophilic active media 6. Chemical sensors to be applied in analysis in aqueous or highly hydrophilic media For the improvement of industrial or R&D procedures related to: 1. The physical manipulation of BODIPY dyes, thanks to the solubilization of the dye to be manipulated in aqueous or highly hydrophilic media 2. The chemical transformation of BODIPY dyes in aqueous or highly hydrophilic media
Patent applied for with priority date 03/23/2022 not yet published