Subphthalocyanines (Spcs) are tripyrrolic macrocycles with a central boron atom. These macrocycles exhibit intense electronic absorption and emission, garnering significant attention for applicability in electronic materials such as photovoltaics and light emitting diodes. Herein, we report a series of fluorinated low-symmetry SPcs with variable peripheral aromaticity and fluorine substitution. Structures are confirmed, in part, by characteristic <sup>19</sup>F NMR chem. shifts. Increased aromaticity in Spcs bathochromically shifts long wavelength absorption (Q band) peripheral substitution has also been shown to do this, these shifts range from ~575 nm to ~675 nm across the series. We have tested members of this series as fluorescence imaging dyes and strong intracellular fluorescence is observed from MDA-MB-231 breast tumor cells by epifluorescence microscopy. The ability to tune fluorescence and biocompatibility by synthetic design holds great promise for this class of molecules as biological imaging probes.

Fluorescence and post-synthetic reactivity mixed fluorinated subphthalocyanines

2019 Spring National Meeting

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