5-(Perfluorooctylthio)acetamidofluorescein (5-FOAF) as a convenient tag for inspecting the surface coverage of fluorinated coatings

Fluorinated compounds are commonly used for anti-stick coating but it is difficult to inspect the coverage of the coating without expensive instruments. Herein, we demonstrated that the 5-(perfluorooctylthio)acetamidofluorescein (5-FOAF) probe can be synthesized in one step and used as a testing reagent to inspect the fluorinated coating on silica- or metal-based surfaces. 5-FOAF is composed of a perfluoroalkyl domain, which has high specific affinity towards fluorinated compounds, and a fluorophore domain, which exhibits fluorescence emission visible by naked eyes. Thus, 5-FOAF will retain on the surface coated with fluorinated compounds but not on the un-coated surface and the emitted fluorescence from the retained tags serves as a semi-quantitative measure of the fluorine coverage across the surface. For this study, silica-based or metal-based surfaces were activated by silane chemistry and then coated with fluorinated compounds. The coating procedure was judiciously optimized to achieve a homogeneous coating. 5-FOAF probe was synthesized in-house and shown to retain on the fluorinated surface 2-5 times stronger than the bare surface. Moreover, by studying the retention on a non-fluoro hydrophobic substrate made of polydimethylsiloxane, the affinity of 5-FOAF with the fluorinated coating was confirmed to be specific and distinguishable from nonspecific hydrophobic interaction. In conclusion, we synthesized a novel chemical, 5-FOAF, and demonstrated its usefulness as a simple testing reagent for fluorinated coatings.