1,5-Diazabicyclo[3.3.0]octadienediones (shortly 9,10-dioxabimanes or "bimanes") are small heterocyclic structures which have important chemical, photochemical and photophysical properties. There are two existing structural isomers for bimane compounds ("syn" and "anti"). The syn-isomers have strong UV absorption properties and high quantum yields and are highly fluorescent. Bimane compounds are widely used for fluorescent labelling in biological systems because of their high photo-stability and bio-compatibility. Despite their unique properties, there is very few examples of study in literature. Because of synthetic difficulties of literature examples and their requirements such as hazardous chemicals, new methodologies are in high demand. In this study, new methods utilising metal catalysis for the effective synthesis of bimane compounds have been developed. Bimanes, which in the literature are synthesised with extreme difficulties and low yields, were synthesised in this work through simple and efficient protocols that employ metal, ligand and base. We further investigated the photophysical properties for all newly synthesized bimane derivatives. In the course of thesis study, a new and efficient method have been developed and optimised for the facile synthesis of benzo-bimane compound via the copper(I) catalyzed intramolecular C-N bond formation reaction. Moreover, with the aid of this new methodology, various analogues of benzo-bimane compound were synthesized in moderate to good yields under mild reaction conditions . Also, photophysical properties of benzo-bimanes were investigated carefully. Keywords : BIMANE, Copper, Ullmann reactions