Pathway-dependent self-assembly of perylene diimide/peptide conjugates in aqueous medium

Yaron Tidhar, Haim Weissman, Sharon G. Wolf, Antonino Gulino, Boris Rybtchinski

Research output: Contribution to journalArticlepeer-review

127 Citations (Scopus)


Most molecular self-assembly strategies involve equilibrium systems, leading to a single thermodynamic product as a result of weak, reversible non-covalent interactions. Yet, strong non-covalent interactions may result in non-equilibrium self-assembly, in which structural diversity is achieved by forming several kinetic products based on a single covalent building block. We demonstrate that well-defined amphiphilic molecular systems based on perylene diimide/peptide conjugates exhibit kinetically controlled self-assembly in aqueous medium, enabling pathway-dependent assembly sequences, in which different organic nanostructures are evolved in a stepwise manner. The self-assembly process was characterized using UV/Vis circular dichroism (CD) spectroscopy, and cryogenic transmission electron microscopy (cryo-TEM). Our findings show that pathway-controlled self-assembly may significantly broaden the methodology of non-covalent synthesis.

Original languageEnglish
Pages (from-to)6068-6075
Number of pages8
JournalChemistry - A European Journal
Issue number22
Publication statusPublished - May 23 2011


  • chirality
  • hydrophobic interactions
  • kinetic control
  • nanostructures
  • self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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