The astounding diversity of structure and function found in proteins and nucleic acids demonstrate Nature's ability to design sophisticated macromolecules with ordered 3D structure for specific chemical functions. These examples in biology have inspired the discovery and design of novel non-biological foldamers, oligomeric molecules which can self-assemble into well structured secondary and tertiary structures. Researchers studying foldamers thus aim to design new classes of macromolecules which share similar folding properties as proteins, but which are constructed from a more diverse set of chemistries. These new non-biological oligomers show promise for a diverse range of applications ranging from therapeutics, antimicrobials, 4,5 catalysts, molecular sensors 8 to nanostructured materials. Considerable experimental research over the last twenty years has identified many new types of foldamers and characterized folding patterns formed by these macromolecules. Researchers have explored natural extensions to canonical biopolymers, in addition to foldamers with novel backbone and side chain chemistries. For example, a number of groups have investigated biomimetic chemistries such as β-, γ-and δ-peptides, 11,12 peptoids and covalently constrained variants of these peptides. Other groups have explored more exotic stabilizing interactions in foldamers, such as π-π interactions and metal-coordination. The success of this research into novel folding chemistries has suggested a range of new applications these chemistries enable. For example, Porter et al. have shown that β-peptides exhibit similar antibacterial properties as their α-peptide counterparts, without triggering the same immune response and with significantly less proteolytic susceptibility. Additionally, groups have explored the feasibility of using DNA molecules and DNA-derivatives as self-assembling nanowires for use in nanoelectronics or as scaffolding for nanoparticle engineering. Chemically-novel foldamers have a wealth of future applications, if we can figure out how to rationally design them. Currently, formulations for novel foldamers is a tedious, painstaking process, limited by low-yield synthesis methods and difficulties in characterization for all but the most stable molecules. Most foldamers that resemble existing biopolymers are synthesized using solid-phase synthesis for their respective linker bond type. These solid-phase synthesis methods suffer from poor protective reaction conditions resulting in low polymer length and low final product yield. Furthermore, methods for foldamer characterization have additional challenges compared to more well-established biopolymer chacterization due to unknown spectroscopic signatures of new foldamer molecules. In addition, the design of novel backbone chemistry that folds in a desired solvent is some what of an art. Gellman describes three challenges when designing novel foldamer molecules. • First, a novel polymeric backbone must be proposed that has adequate folding propensities and can form structure at the polymer level.