A Showcase of Functional Fluorous Materials and Their Applications

Abstract

This thesis highlights conjugated organic materials functionalized with fluoroalkyl chains and explores their applications in material chemistry. In Chapter 1, we begin with a brief introduction of incorporation of fluorine into materials and its effect on materials properties. An introduction to dynamically reconfigurable complex emulsions reported by our group and their applications in sensing is also provided. In Chapter 2, we disclose the synthesis and photophysical properties of “fluorofluorescent” perylene bisimides, where fluoro- refers to both fluorine and fluorescence. These perylene bisimides were utilized to realize the concept of a fluorofluorescent solar concentrator. In Chapter 3, we report the synthesis and photophysical properties of fluorous phthalocyanines and subphthalocyanines. We then explored these molecules’ Faraday rotation properties in organic and fluorous solvents. In Chapter 4, we describe the applications of the perylene bisimide and subphthalocyanine dyes by incorporating them into fluorescent Janus emulsions. We also report the synthesis of fluorous soluble black hole quencher dyes, which were found to be more absorptive than fluorous soluble subphthalocyanines. The emulsions were engineered to function as biosensors for the detection of Salmonella, Zika virus, Listeria, and antiSARS-CoV-2 spike antibody. In Chapter 5, we report the utilization of the Heck reaction for facile access to functional fluorous materials. We also showcase how this fluoroalkenyl side chain turns out to be an important functional group for lithium primary batteries.