Dynamic covalent chemistry has emerged as a facile approach to assemble molecular architectures that are more robust and stable than those attained from classical self-assembly mechanisms using transient intermolecular interactions. We incorporate boronic acid and catechol pendant groups onto peptoid-based oligomers that, upon mixing in aqueous solution, participate in reversible condensation reactions and assemble into molecular ladders. Here, we describe the synthesis of the precursor oligomers and the resulting assembled structures from reactions between short complementary peptoid strands of boronic acids and catechol. The generated structures were characterized using matrix-assisted laser desorption/ionization mass spectrometry, confirming successful molecular ladder fabrication. The described work lays the foundation for a versatile approach to the fabrication of complex and robust proteomimetic nanostructures.

Information-directed assembly of molecular ladders bearing boronate ester rungs

255th National Meeting (2018)

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