A large number of ferrocene-containing BODIPYs, azaBODIPYs, and BOPHYs along with several examples of non-innocent transition-metal aza-dipyrromethenes have been prepared and characterized by UV-Vis-NIR, NMR, HRMS, and X-ray crystallography. The redox properties of all target compounds were investigated by electrochemical and spectroelectrochemical methods. The experimental electronic, spectroscopic, and geometric parameters of the organometallic BODIPYs, azaBODIPYs, and BOPHYs as well as transition-metal aza-dipyrromethenes were correlated with DFT and TDDFT calculations.