This thesis describes the synthesis of a novel family of 4,4─difluoro─4─bora─3a─4a─diaza─s─indacenes for material and education applications (BODIPYs). This thesis also presents the exploration of their optical and electrochemical properties, as well as potential for application in dye─sensitised solar cells, and synthetic laboratories. Chapter 1 gives an overview of the photophysical of chromophores of large organic electronics. BODIPYs are introduced as suitable building blocks for such applications, and synthetic approaches for extending the conjugation of these fluorophores are presented. Chapter 2 gives an overview the development of an engaging senior undergraduate laboratory course based on BODIPY that reinforces traditionally important technical skills and explore property─directed synthesis & research. Chapter 3 describes the use of the redox robust ferrocene as electron donor in the synthesis of ferrocene─BODIPY dyes for DSSC applications. Chapter 4 explores the effects of confined intramolecular π─stacking on the physicochemical properties of π─π BODIPY dimers in cyclophane architectures through the synthesis of a novel cyclophane consisting of BODIPY and anthracene moieties.