Fluorination is a common technique for enhancing the chemical inertness and thermal stability of organic molecules. This technique was applied in the production of robust phthalocyanines, catalytic and/or photocatalytic materials designed to function in harsh oxidative environments. As phthalonitriles are common phthalocyanine precursors, their fluorination is the preferred path for fluorine introduction in the phthalocyanine macrocycle. The susceptibility of fluorinated phthalonitriles to aromatic nucleophilic substitutions leads to functionalization options, the amino derivatives being the focus of this report. Amino fluorinated phthalocyanines comprise an electron donor → acceptor substituents combination, which lowers the phthalocyanine efficiency for singlet oxygen photo production likely due to the amino nitrogen lone-pair conjugation with the electron-deficient aromatic ring. Competitive conjugation of the lone-pair with a carbonyl group introduced via acylation weakens the donor effect of the amino group and thus enhances the catalytic efficiency of the phthalocyanines. By applying this strategy amino fluorinated phthalonitriles and phthalocyanines were converted to acetyl, bis-acetyl, succinyl, perfluoro-butyryl derivatives. Spectroscopic data and X-ray single-crystal determinations confirmed the synthesis results while providing atomic-level structural information for 4 acylated phthalonitriles and 6 acetylated phthalocyanines.

Synthesis, X-ray structures, photo-physics and singlet oxygen production of fluorinated phthalocyanines

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.