Title

A Comparison of the Photophysical, Electrochemical and Cytotoxic Properties of -(2-, 3- and 4-Pyridyl)-BODIPYs and Their Derivatives

Document Type

Article

Publication Date

7-7-2022

Abstract

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 -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 and 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 showed the highest relative fluorescence quantum yield in organic solvents, which was further enhanced by the use of a bulky counter anion (PF). 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--(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.

Publication Source (Journal or Book title)

Sensors (Basel, Switzerland)

This document is currently not available here.

Plum Print visual indicator of research metrics
PlumX Metrics
  • Citations
    • Citation Indexes: 2
  • Usage
    • Abstract Views: 33
  • Captures
    • Readers: 10
  • Mentions
    • Blog Mentions: 1
see details

COinS