We report the series of G1 and G1.5 dendritic systems with mono-T8 SQs and DDSQ as specific types of dendron and dendrimer cores, respectively. The trivinyl- and tri(chloromethyl)-derivatives were obtained via hydrolytic condensation followed by the hydrosilylation reaction, optimized to yield selectively β-products. Their structures were confirmed by spectroscopic and XRD analyses. It is the first example of double-decker SQs used as cores for the construction of a low generation of dendrimer featuring specific dumbbell frameworks expanding in two or four directions.