In this account, we discuss the common molecular features and the related chemistry concepts across several different areas of organic electronics, including molecular semiconductors and single-molecule junctions. Despite seemingly diverse charge transport mechanisms and device set-ups, various molecular electronics systems can benefit from the same fundamental principles of physical organic chemistry, based upon the electronic structure and geometry of their molecular building blocks and the intermolecular interactions between them. This is not an exhaustive review of organic electronics, but rather a focused account of primarily our own recent efforts aimed at developing a unified approach to understanding and designing conductive molecular species for diverse electronic applications.