‘A fluorophore for the future’ : design and synthesis of novel BODIPY derivatives

Abstract

This thesis provides insight into the chemistry of the BODIPY family of fluorophores. It describes the synthetic methods undertaken to attempt various structural modifications of the core BODIPY framework. Three different types of BODIPY themed molecules were targeted for synthesis; HBC-coupled BODIPY derivatives, metal coordinating ligand-type BODIPY molecules, and dual BF2 core containing frameworks.

Chapter One, describes the background of BODIPY molecules, their chemistry and their large role within fluorescence based research and applications. This chapter also provides a short review of all relevant BODIPY derivatives and the related research. Chapter Two introduces the synthetic schemes investigated for forming HBC appended BODIPY derivatives and the results achieved here. Chapter Three presents the research into developing the relatively novel metal coordinating BODIPY molecules, and the promising syntheses carried out to form multiple BODIPY derivatives with metal interactive capability. Chapter Four outlines the research around creating BODIPY themed, dual BF2 core systems, expanding on the fairly recent discovery of the BOPHY framework within the BODIPY research community. Chapter Five summarise the results and outlines the conclusions gained from the project along with the potential future direction of the research. Chapter Six, describes the experimental methodology of all adapted and newly formed syntheses of molecules formed throughout the thesis.

One novel derivative is described, with the full crystal structure and analytical characterisation, along with several new methods for synthesis and purification of established BODIPY compounds.