Subphthalocyanine (SubPc)-fused dimers and trimers bearing fluorine, iodine, and thioether peripheralsubstituents were synthesized and characterized. Absorption spectroscopy and electrochemical studiesrevealed (i) that the substituents have a strong effect on the electronic properties of the macrocycles and(ii) that there is good communication between the subphthalocyaninic moieties within the oligomericstructures. Theoretical calculations at DFT/6-31G(d,p) computational level and electron density studiessupport the experimental findings. The frontier orbitals in the dimers and trimers were also shown to besignificantly altered with respect to those of SubPcs as a consequence of the extension of the conjugationassociated with symmetry breaking. Time-dependent density functional theory calculations reproducedthe differences observed in the UV-vis spectra of the fused dimers and the monomeric SubPcs.