π-Extended BODIPY Analogues: Synthesis, Electronic Structure, Potential Utility for in vivo Imaging Applications and Cytotoxicity

Abstract

A series of 3,5-distyryl and meso-morpholino/hydroquinoline BODIPY dyes have been synthesized and characterized. The electronic structure was investigated by optical spectroscopy, electrochemistry and TD-DFT calculations. In addition, they fluoresce in the biological window and are hence potentially suitable for use as cellular imaging agents. The meso-1,2,3,4-isoquinoline substituted BODIPYs 3с-d interact strongly with DNA and this enhances their ability to act as bioimaging agents. In contrast, the meso-morpholine substituted BODIPYs 3a-b were found to have higher cell toxicity.