Firefly luciferin, also known as D-luciferin, is a naturally occurring bioluminescent compound, found in various insects. This small molecule and its synthetic analogues have been used for bioluminescent imaging (BLI). This thesis presents the synthesis of novel D-luciferin analogues that incorporate an amine functional group, to explore the development of red-shifted and brighter analogues. The opening chapter of this thesis discusses the history of bioluminescence and its studies. There is then a greater focus on the history of D-luciferin and luciferase enzyme, as well as the effect various changes to either of the two components has on the bioluminescence. A review of synthetic analogues of D-luciferin, previously reported in the literature, including their bioluminescent properties is presented. The introduction ends with a discussion of the current challenges in the field of bioluminescent reporters and the aim of this project to explore novel amine-based analogues to explore improved emission wavelength and brightness of existing analogues. The second chapter discusses the synthesis of novel amine infra-luciferin analogues. This chapter presents a convergent synthesis of amine infra-luciferin analogues. The third chapter details the synthesis of a C-4 substituted amine D-luciferin analogue. A variety of attempted methods to construct the benzothiazole moiety are discussed. The fourth chapter summarises the results and suggests future work for both the amine infra-luciferins and the C-4 substituted amine luciferin, as well as outlines of potential future work. The final chapter presents experimental procedures and analytical data. The thesis is fully referenced to the primary literature.