From only a few simple monomers, biological polymers can access complex functions such as catalyzing reactions, storing information, and recognizing pathogens. Developing synthetic protocols to mimic the complexity and function of biopolymers will require a scalable and practical method to create monodisperse, sequence and architecturally defined macromolecules. The strategy developed herein integrates a known, but underutilized, methodology in synthetic polymer chemistry called iterative exponential growth (IEG) with modern developments in continuous flow chemistry to generate sequence-defined macromolecules. The IEG methodology involves partitioning a common starting material in half, each half undergoes two separate and complementary deprotection reactions, and those halves are then recombined and coupled together. Because each doubling of molecular weight requires three different reactions, however, this method is exceedingly laborious when done with standard batch chemistry.<br/>To overcome the challenges associated with IEG, we have developed a novel marriage of IEG with continuous flow chemistry (“Flow-IEG”). Taking advantage of the automated and exacting control over mixing, thermal conditions, and reaction time in continuous flow, we have developed a system capable of performing iterative deprotection and coupling steps in rapid succession, allowing an exponential growth of monodisperse polymers. Significantly, <i>the flow system performs 3 reactions – two deprotections, an in-line purification and a coupling step – with a total residence time of under ten minutes.</i> The generality of this approach and its potential for automation holds significant potential for the synthesis of materials in a number of high-value applications.

Flow IEG: A scalable route to sequence and architecturally defined unimolecular macromolecules

249th National Meeting (2015)

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