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Title: Solid-phase synthesis of self-assembling multivalent π-conjugated peptides

Here, we present a completely solid-phase synthetic strategy to create three- and four-fold peptide-appended π-electron molecules, where the multivalent oligopeptide presentation is dictated by the symmetries of reactive handles placed on discotic π-conjugated cores. Carboxylic acid and anhydride groups were viable amidation and imidation partners, respectively, and oligomeric π-electron discotic cores were prepared through Pd-catalyzed cross-couplings. Due to intermolecular hydrogen bonding between the three or four peptide axes, these π-peptide hybrids self-assemble into robust one-dimensional nanostructures with high aspect ratios in aqueous solution. The preparation of these systems via solid-phase methods will be detailed along with their self-assembly properties, as revealed by steady-state spectroscopy and transmission electron microscopy and electrical characterization using field-effect transistor measurements.
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  1. John Hopkins Univ., Baltimore, MD (United States)
Publication Date:
Grant/Contract Number:
Published Article
Journal Name:
ACS Omega
Additional Journal Information:
Journal Volume: 2; Journal Issue: 2; Journal ID: ISSN 2470-1343
American Chemical Society (ACS)
Research Org:
John Hopkins Univ., Baltimore, MD (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE; bioelectronics; catalysts; electron microscopy; molecular structure; nanostructured materials; nanostructures; peptides and proteins; self-assembly
OSTI Identifier:
Alternate Identifier(s):
OSTI ID: 1345216