Fluorous porphyrinoids such as perfluorophenyl porphyrin (TPPF20) and hexadecfluorophthalocyanine (PcF16) are excellent platforms to teach a variety of undergraduate techniques and principles. These intensely colored chromophores can have strong fluorescence, thus are easily characterized by optical and emission spectra and visualized by eye in chromatography. We previously demonstrated that the porphyrins can be readily made in a solvent-free reaction that illustrates the principles of green chemistry, and later that the Pc can be made similarly. Recently, we reported that the TPPF20 platform is ideal to teach physical organic chemistry principles of nucleophilic aromatic substitution by correlating Arrhenius plots with the properties of the nucleophile: primary alcohols, amines, and sulfides. The rate versus temperature data comes from thin-layer chromatography using the student's cellphones to take pictures and 'image-j' to quantify the area and intensity of the spot. The fluorous platforms can also be used to form supramolecular materials.

Porphyrinoids as platforms for chemical education

2019 Spring National Meeting

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