Although “ordered” organic π-conjugated assemblies outperform “disordered” ones in many optoelectronic device applications, we are far from being able to port the well-understood supramolecular recipes of π-systems from solution to solid-state device environments. For the past several years we have been exploring hydrogen bond (H-bond) directed self-assembly of π-systems along these lines, for example, to enhance their absorption and charge transport properties for organic photovoltaic (OPV) applications. Various examples of oligothiophenes outfitted with heterocycles capable of forming H-bonded “rosettes” will be discussed in this context. The second part of the talk will introduce new monomers derived from [2.2]paracyclophane (pCp) that are capable of robust H-bond directed self-assembly into one-dimensional nanostructures in solution and the solid state. The design introduces transannular (intramolecular) H-bonds between pairs of pseudo-ortho-positioned amides as a way to preorganize the molecules for intermolecular H-bonding with two neighbors. The result is formation of homochiral, one-dimensional pCp stacks that show supramolecular polymer signatures in solution.