Dynamic covalent chemistry, in conjunction with template-directed assembly, enables the fabrication of extended nanostructures that are both precise and tough. Here, we demonstrate the dynamic covalent assembly of peptoid-based molecular ladders with up to 16 rungs <i>via</i> scandium (III)-catalyzed imine metathesis. Owing to their monomer diversity and synthetic accessibility, sequence-specific oligopeptoids bearing dynamic covalent pendant groups were employed as precursors for molecular ladder fabrication. The assembled structures were characterized using matrix-assisted laser desorption/ionization (MALDI) mass spectrometry and gel permeation chromatography (GPC), confirming successful molecular ladder fabrication. To determine the mechanism of hybridization registry, a kinetics study was performed to examine the formation of molecular ladders with different lengths by MALDI mass spectrometry. In addition, distance measurements using Förster resonance energy transfer (FRET) were employed to confirm the registry mechanism.

Dynamic covalent assembly of peptoid-based ladder oligomers and its registry mechanism

252nd National Meeting (2016)

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