The synthesis and characterization of two benzo-indaceno-thiophene compounds (anti-BIT and syn-BIT) are described. Two sequential Suzuki cross-couplings utilizing the halogen selectivity of this reaction permit modular assembly of unsymmetrical indeno[1,2-b]fluorene analogues. Analysis of their cyclic voltammetry and UV-vis spectra reveal that the optical and electrochemical properties of the BITs lie between those of indeno[1,2-b]fluorenes and indacenodithiophene.