Bidentate ligands have made an indelible contribution to chemistry, with phosphines such as 1,2-bis(diphenylphosphino)ethane (dppe) and 1,1’-bis(diphenylphosphino)ferrocene (dppf) standing out as chelating ligands of choice. Since conception, N-heterocyclic carbenes (NHCs) have been compared to phosphines with regards to ligand properties. However, the chemistry of bidentate NHCs has languished in comparison, primarily due to water sensitivity and the prevalence of multiple undesirable coordination modes beside chelation. The current thesis presents a foray into bidentate carbene chemistry from a ligand-design perspective. A modular, high yielding, and convenient method to access bidentate NHC ligands is initially provided. Subsequently, the chelating ability of the ligand motif is exemplified with the stabilization of rare low-valent complexes of nickel. The second half of the thesis describes the effect of electronic tuning at the carbenes upon synthesis of the first bis[cyclic (alkyl)(amino)carbene] and a rare bis(mesoionic carbene) to vary the degree of mesomeric metal-ligand interactions. Such interactions proved key in the successful isolation of highly reactive late-transition-metal chelate complexes. The findings described herein are expected to pave the way towards isolation of more reactive chelate complexes of other low-valent transition metals and main group elements. It is hoped that current additions to the underdeveloped repertoire of isolable biscarbene compounds will bring more attention to this ligand class in small-molecule activation and catalysis.