Gated electron sharing within dynamic naphthalene diimide-based oligorotaxanes

Alyssa-Jennifer Avestro, Daniel M Gardner, Nicolaas A Vermeulen, Eleanor A Wilson, Severin T Schneebeli, Adam C Whalley, Matthew E Belowich, Raanan Carmieli, Michael R Wasielewski, J Fraser Stoddart

Research output: Contribution to journalArticlepeer-review


The controlled self-assembly of well-defined and spatially ordered π-systems has attracted considerable interest because of their potential applications in organic electronics. An important contemporary pursuit relates to the investigation of charge transport across noncovalently coupled components in a stepwise fashion. Dynamic oligorotaxanes, prepared by template-directed methods, provide a scaffold for directing the construction of monodisperse one-dimensional assemblies in which the functional units communicate electronically through-space by way of π-orbital interactions. Reported herein is a series of oligorotaxanes containing one, two, three and four naphthalene diimide (NDI) redox-active units, which have been shown by cyclic voltammetry, and by EPR and ENDOR spectroscopies, to share electrons across the NDI stacks. Thermally driven motions between the neighboring NDI units in the oligorotaxanes influence the passage of electrons through the NDI stacks in a manner reminiscent of the conformationally gated charge transfer observed in DNA.

Original languageEnglish
Pages (from-to)4442-9
Number of pages8
JournalAngewandte Chemie International Edition
Issue number17
Publication statusPublished - 22 Apr 2014


  • Catalysis
  • Electron Spin Resonance Spectroscopy
  • Electrons
  • Hydrogen Bonding
  • Imides/chemistry
  • Models, Molecular
  • Molecular Conformation
  • Naphthalenes/chemistry
  • Rotaxanes/chemistry

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