Exploring Bodipy Dyes in Light-Harvesting, Energy Transfer and Bio-Inspired Probe Designs

Attempts to mimic Nature and create artificial photosynthetic systems has transformed from an active chemical curiosity to a full-blown research pursuit, owing to our need for sustainable energy generation. To this end, this thesis explores the use of the dye, BODIPY (4-4’-difluoro-4-bora-3a,4a-diaza-s-indacene). BODIPY dyes have gained considerable attention owing to their highly desirable properties, such as strong absorption, fluorescence quantum yields, good chemical and photo-stability. These desirable physiochemical properties have led to materials that can be used for chemosensors, biological labeling agents, fluorescent switches, laser dyes, and organic sensitizers. For this thesis, a pentamethylBODIPY (2.1a) derivative was further functionalized in order to examine its potential for a myriad of applications.

Energy extraction in terms of dye-sensitized solar cells (DSSCs) requires electronically asymmetric molecules as building blocks. In Chapter 2, pentamethylBODIPY (2.1a) was modified using Schiff-base chemistry to create a family of dye building blocks. In this chapter, mono ß-substitution was used to break symmetry in this potential BODIPY building block, thus tuning the electronic and optical properties.