Highly fluorinated compounds, in which all C<sub>sp3</sub>-H bonds have been replaced by C<sub>sp3</sub>-F bonds, are referred to as “fluorous.” These compounds phase-separate from both aqueous and organic media. The orthogonality of the fluorous phase has led to many applications in biology, medicine, and materials. To better enable applications of the fluorous phase, especially in the context of biological experiments, there is a need to develop fluorous fluorophores. Various chromophore scaffolds with fluorous chain substitutions, such as BODIPY, rhodamine, perylene bisimide, and tetraphenyl porphyrin have been published. These previous reports either do not demonstrate fluorous solubility or have incomplete photophysical characterization. In this work, we report a synthesis of highly fluorinated indolenine cyanine dyes and create a panel of fluorophores with varied weight percent fluorine which allows for the photophysical properties of these compounds to be fully characterized in fluorous, organic, and aqueous media. We find that the cyanines are more fluorous-soluble than another previously reported fluorous fluorophore, the rhodamine. The fluorous cyanines’ fluorescence quantum yields are comparable to literature in fluorous media, and the quantum yields increase in organic media. Furthermore, the fluorous chains lend photostability to the dyes. This work provides insight into the synthesis of truly fluorous-soluble fluorophores and allows for comparisons between how fluorous, organic, and aqueous media affect photophysics.

Fluorous-soluble cyanines and their photophysical characterizations in aqueous, organic, and fluorous media

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.