Foldamer Heterosequences: A Modular Approach to Customizable Molecular Containers

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The focus of this research is the development of methodology for the use of heterosequences in a modular way to customize the space inside molecular compartments derived from conformationally ordered oligomers. Statistical computer aided design (SCAD) algorithms will be developed to help rationally design both the volume requirements and concave surfaces inside these compartments complementary to a particular guest, intermediate or transition state of interest. Improved methods for the preparation of oligomeric phenylene ethynylene (PE) heterosequences will be developed and new building blocks will be explored in order to diversify the size, shape and internal functionalization of compartments created by folded PE heterosequences. Optimized sequences identified by SCAD will be prepared and binding affinity to N,N'-diphenylpiperazines will be measured and compared to a set of isomeric control sequences predicted to have low affinity for this ligand. Building on these developments, the concept of catalytic reactive sieving is proposed as a means to achieve size-based selective activation of reactive substrates. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Jeffrey S. Moore of the Department of Chemistry at the University of Illinois at Urbana-Champaign and Dr. Jeffrey G. Saven of the Department of Chemistry at the University of Pennsylvania. This collaborative effort will focus on the development of methodology for the construction oligomeric sequences that will fold into nanoscale containers. This approach, guided by theory and experiment, will allow the production of a customized space inside a molecular compartment and this, in turn will bring about specific molecular recognition for the eventual purpose of controlling chemical reactivity. The project has the broader impact of integrating activities in both theory and experimentation thus providing an excellent setting for the multidisciplinary training of undergraduate, graduate and postdoctoral students.