Induction of Motion in a Synthetic Molecular Machine: Effect of Tuning the Driving Force

Jacob Baggerman, Natalia Haraszkiewicz, Piet G. Wiering, Giulia Fioravanti, Massimo Marcaccio, Francesco Paolucci*, Euan R. Kay, David A. Leigh, Albert M. Brouwer

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Rotaxane molecular shuttles were studied in which a tetralactam macrocyclic ring moves between a succinamide station and a second station in which the structure is varied. Station2 in all cases is an aromatic imide, which is a poor hydrogen-bond acceptor in the neutral form, but a strong one when reduced with one or two electrons. When the charge density on the hydrogen-bond-accepting carbonyl groups in station2 is reduced by changing a naphthalimide into a naphthalene diimide radical anion, the shuttling rate changes only slightly. When station2 is a pyromellitimide radical anion, however, the shuttling rate is significantly reduced. This implies that the shuttling rate is not only determined by the initial unbinding of the ring from the first station, as previously supposed. An alternative reaction mechanism is proposed in which the ring binds to both stations in the transition state.

Original languageEnglish
Pages (from-to)5566-5577
Number of pages12
JournalChemistry - A European Journal
Volume19
Issue number18
DOIs
Publication statusPublished - Apr 2013

Keywords

  • electrochemistry
  • molecular shuttles
  • photochemistry
  • reaction mechanisms
  • rotaxanes
  • RESOLVED VIBRATIONAL SPECTROSCOPY
  • PULSE-RADIOLYSIS
  • ENTROPY-DRIVEN
  • DONOR-ACCEPTOR
  • ROTAXANE
  • SHUTTLES
  • MECHANISM
  • MOTORS
  • RADICALS
  • IMIDE

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