Silicon-based materials are crucial for conventional electronics. The fascinating properties of the new two-dimensional material silicene, the silicon analogue of graphene (one atom-thick silicon sheets), offer a potential bridge between conventional and molecular electronics. The ground-state configuration of silicene is buckled, which compromises optimal constructive overlap of p orbitals. Because silicene is not planar like graphene, it has a lower intrinsic electron/hole mobility than graphene. This motivates a search for improved, alternative, planar materials. Miniaturization of silicene/graphene hybrid monolayers affords diverse silicon organic and-inorganic molecules, whose potential as building blocks for molecular electronics is unexplored. Additionally, hybridization of pure silicon rings (or sheets) is a versatile way to control the geometrical and electronic characteristics of the aromatic ring. In this work we systematically investigate, computationally, architectures and electronic structures of a series of hybrid silaaromatic monomers and fused-ring oligomers. This includes the thermochemistry of representative reactions: hydrogenation and oxidation. The effect of various skeletal substituents of interest is elucidated as well. We show that the specific location of carbon and silicon atoms, and their relative populations in the rings are crucial factors controlling the molecular geometry and the quasi-particle gap. Furthermore, we suggest that electron-withdrawing substituents such as CN, F, and CF3 are promising candidates to promote the air-stability of silaaromatics. Finally, on the basis of the analysis of benzene-like silaaromatic molecules, we discuss a set of alternative, prototype ring molecules that feature planarity and delocalized r bonds. These motifs may be useful for designing new extended materials.