Fluorous phthalocyanines and subphthalocyanines
Name
doi-10.1142 S1088424620500182.pdf
Description
Accepted version
Size
10.57 MB
Format
Unknown
Checksum (MD5)
d5dc70ab8f620b85de12d1f8718f0125
Author(s)
Yoshinaga, Kosuke
Delage-Laurin, Leo
Swager, Timothy M
Date Issued
August 2020
Journal
Journal of Porphyrins and Phthalocyanines
Publisher
World Scientific Pub Co Pte Lt
Citation
Yoshinaga, Kosuke, Delage-Laurin, Leo and Swager, Timothy M. "Fluorous phthalocyanines and subphthalocyanines." Journal of Porphyrins and Phthalocyanines, 24, 8 (August 2020): 1074-1082.
Version
Author's final manuscript
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-Noncommercial-Share Alike
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1142/S1088424620500182
