Fluorous phthalocyanines and subphthalocyanines
Author(s)Yoshinaga, Kosuke; Delage-Laurin, Leo; Swager, Timothy M
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Incorporating fluorine atoms into a molecule can endow it with various unique properties that enable materials applications. Selective solubility in fluorous solvents is achieved by a high fluorine content and selective partitioning into perfluorinated liquids over organic and aqueous phases provides orthogonal opportunities for chemistry and materials assembly. Although there is a growing number of partially fluorinated molecules, there are insufficient structural design principles to produce diverse fluorous soluble dyes. Herein, we report the synthesis of six fluorous phthalocyanine and subphthalocyanine dyes, and study their properties in the fluorous phase. Phthalocyanines generally display limited solubility and we also observed apparent aggregation in the fluorous phase. However, the nonplanar subphthalocyanines showed greater solubility. Subphthalocyanines also displayed fluorescence in selected solvents, and their emissive properties were investigated. The materials described expand the library of fluorous dyes and provide insights for the design of new molecules with fluorous solubility.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Journal of Porphyrins and Phthalocyanines
World Scientific Pub Co Pte Lt
Yoshinaga, Kosuke, Delage-Laurin, Leo and Swager, Timothy M. "Fluorous phthalocyanines and subphthalocyanines." Journal of Porphyrins and Phthalocyanines, 24, 8 (August 2020): 1074-1082.
Author's final manuscript