Dynamic covalent assembly of peptoid-based ladder oligomers by vernier templating

Tao Wei, Jae Hwan Jung, Timothy F. Scott

Research output: Contribution to journalArticleResearchpeer-review

29 Citations (Scopus)


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 12 rungs via scandium(III)-catalyzed imine metathesis by employing the principle of Vernier templating, where small precursor units with mismatched numbers of complementary functional groups are coreacted to yield larger structures with sizes determined by the respective precursor functionalities. 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 generated structures were characterized using matrix-assisted laser desorption/ionization mass spectrometry and gel permeation chromatography, confirming successful molecular ladder fabrication.

Original languageEnglish
Pages (from-to)16196-16202
Number of pages7
JournalJournal of the American Chemical Society
Issue number51
Publication statusPublished - 30 Dec 2015
Externally publishedYes

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