TY - JOUR
T1 - Dynamic covalent assembly of peptoid-based ladder oligomers by vernier templating
AU - Wei, Tao
AU - Jung, Jae Hwan
AU - Scott, Timothy F.
PY - 2015/12/30
Y1 - 2015/12/30
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84953432984&partnerID=8YFLogxK
U2 - 10.1021/jacs.5b11251
DO - 10.1021/jacs.5b11251
M3 - Article
AN - SCOPUS:84953432984
SN - 0002-7863
VL - 137
SP - 16196
EP - 16202
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 51
ER -