We report the stereoselective synthesis of the cis isomer of F40PcZn, a perfluorophthalocyanine peripherally substituted by both aromatic, F and aliphatic, RF groups. In F16Pc, F40Pc and F64Pc scaffolds, the 8 peripheral positions are substituted to 0, 50 and 100% extents by RF groups, respectively, thus defining a substitution parameter S with values 0, 0.5 and 1. For S = 0.5 a single crystal X-ray structure reveals the formation of dimers exhibiting p-stacking of the type expected for S = 0. Aggregation of F40PcZn in solution is solvent dependent, likely limited by the bulkiness of the moiety of the type found for S = 1. The generation of singlet oxygen was also demonstrated to occur at rates comparable with that observed for S = 1, about twice that observed for S = 0.    The fluorinated environment insures the high stability of the phthalocyanine macrocycle during the production of singlet oxygen and oxidation of �-citronellol to hydroperoxides, thus recommending the F40Pc for additional catalytic processes developments using aerobic pathways.                    Acknowledgment  Support from the National Science Foundation is gratefully acknowledged

Stereoselective-induced variable aggregation and photocatalysis of fluorinated phthalocyanines lacking C-H bonds

247th National Meeting (2014)

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