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A Comparison of the Photophysical, Electrochemical and Cytotoxic Properties of meso-(2-, 3- and 4-Pyridyl)-BODIPYs and Their Derivatives
| Content Provider | MDPI |
|---|---|
| Author | Caroline, Ndung’U LaMaster, Daniel J. Dhingra, Simran Mitchell, Nathan H. Bobadova-Parvanova, Petia Fronczek, Frank R. Elgrishi, Noémie Vicente, Maria Da Graça H. |
| Copyright Year | 2022 |
| Description | Boron dipyrromethene (BODIPY) dyes bearing a pyridyl moiety have been used as metal ion sensors, pH sensors, fluorescence probes, and as sensitizers for phototherapy. A comparative study of the properties of the three structural isomers of meso-pyridyl-BODIPYs, their 2,6-dichloro derivatives, and their corresponding methylated cationic pyridinium-BODIPYs was conducted using spectroscopic and electrochemical methods, X-ray analyses, and TD-DFT calculations. Among the neutral derivatives, the 3Py and 4Py isomers showed the highest relative fluorescence quantum yields in organic solvents, which were further enhanced 2-4-fold via the introduction of two chlorines at the 2,6-positions. Among the cationic derivatives, the 2catPy showed the highest relative fluorescence quantum yield in organic solvents, which was further enhanced by the use of a bulky counter anion (PF_{6}$^{−}$). In water, the quantum yields were greatly reduced for all three isomers but were shown to be enhanced upon introduction of 2,6-dichloro groups. Our results indicate that 2,6-dichloro-meso-(2- and 3-pyridinium)-BODIPYs are the most promising for sensing applications. Furthermore, all pyridinium BODIPYs are highly water-soluble and display low cytotoxicity towards human HEp2 cells. |
| Starting Page | 5121 |
| e-ISSN | 14248220 |
| DOI | 10.3390/s22145121 |
| Journal | Sensors |
| Issue Number | 14 |
| Volume Number | 22 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2022-07-07 |
| Access Restriction | Open |
| Subject Keyword | Sensors Bodipy Pyridinium Fluorescence |
| Content Type | Text |
| Resource Type | Article |
