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 journalArticle

32 Citations (Scopus)

Abstract

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. Birds of a feather flock together: Mutually π-stacked small-molecule naphthalene diimide (NDI) [24]crown-8 derivatives self-assemble dynamically on a repeating -(CH2CH2NH2 +CH 2)-template to afford the stepwise evolution of discrete-length oligorotaxanes, which are shown to communicate electronically through their co-facially interacting π-surfaces, sharing electrons across linear arrays containing one, two, three, and four NDI units as determined by cyclic voltammetry and EPR/ENDOR spectroscopies.

Original languageEnglish
Pages (from-to)4442-4449
Number of pages8
JournalAngewandte Chemie - International Edition
Volume53
Issue number17
DOIs
Publication statusPublished - Apr 22 2014

Fingerprint

Naphthalene
Electrons
Electron Spin Resonance Spectroscopy
Cyclic voltammetry
Paramagnetic resonance
Charge transfer
Spectrum Analysis
Spectroscopy
Feathers
Birds
Crowns
Scaffolds
Self assembly
Oxidation-Reduction
naphthalenediimide
DNA
Electronic equipment
Derivatives
Molecules

Keywords

  • electron transport
  • mechanically interlocked molecules
  • radical anions
  • self-assembly
  • template-directed synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Medicine(all)

Cite this

Avestro, A. J., Gardner, D. M., Vermeulen, N. A., Wilson, E. A., Schneebeli, S. T., Whalley, A. C., ... Stoddart, J. F. (2014). Gated electron sharing within dynamic naphthalene diimide-based oligorotaxanes. Angewandte Chemie - International Edition, 53(17), 4442-4449. https://doi.org/10.1002/anie.201309680

Gated electron sharing within dynamic naphthalene diimide-based oligorotaxanes. / Avestro, Alyssa Jennifer; Gardner, Daniel M.; Vermeulen, Nicolaas A.; Wilson, Eleanor A.; Schneebeli, Severin T.; Whalley, Adam C.; Belowich, Matthew E.; Carmieli, Raanan; Wasielewski, Michael R; Stoddart, J. Fraser.

In: Angewandte Chemie - International Edition, Vol. 53, No. 17, 22.04.2014, p. 4442-4449.

Research output: Contribution to journalArticle

Avestro, AJ, Gardner, DM, Vermeulen, NA, Wilson, EA, Schneebeli, ST, Whalley, AC, Belowich, ME, Carmieli, R, Wasielewski, MR & Stoddart, JF 2014, 'Gated electron sharing within dynamic naphthalene diimide-based oligorotaxanes', Angewandte Chemie - International Edition, vol. 53, no. 17, pp. 4442-4449. https://doi.org/10.1002/anie.201309680
Avestro AJ, Gardner DM, Vermeulen NA, Wilson EA, Schneebeli ST, Whalley AC et al. Gated electron sharing within dynamic naphthalene diimide-based oligorotaxanes. Angewandte Chemie - International Edition. 2014 Apr 22;53(17):4442-4449. https://doi.org/10.1002/anie.201309680
Avestro, Alyssa Jennifer ; Gardner, Daniel M. ; Vermeulen, Nicolaas A. ; Wilson, Eleanor A. ; Schneebeli, Severin T. ; Whalley, Adam C. ; Belowich, Matthew E. ; Carmieli, Raanan ; Wasielewski, Michael R ; Stoddart, J. Fraser. / Gated electron sharing within dynamic naphthalene diimide-based oligorotaxanes. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 17. pp. 4442-4449.
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