Herein we report the optimised synthesis of a versatile bis(imidazole)carbazole framework 4, a precursor to our previously reported C–N–C bis(NHC) pincer ligand, bimca. We have also used 4 as a basis for constructing a library of fully characterised bis(imidazolium) salt pre-ligands which vary the steric and electronic parameters of the subsequently formed NHC moieties. Lithium bis(NHC)carbazolide complexes Li(bimca^R) were generated from their parent bis(imidazolium)carbazole salts, and their behavior in solution and the solid state is discussed.