Subphthalocyanine-Stoppered [2]Rotaxanes: Synthesis and Size/Energy Threshold of Slippage

Yuto Kage, Soji Shimizu, Gabriele Kociok-Köhn, Hiroyuki Furuta, G. Dan Pantoş

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Abstract

Subphthalocyanine (SubPc)-stoppered [2]rotaxanes were synthesized for the first time. The rotaxane bearing unsubstituted SubPc as a stopper exhibited an equilibrium of slipping-on and slipping-off, whereas a perfluorinated SubPc stopper completely blocked slippage of the ring due to its slightly larger size. Kinetic studies revealed the Gibbs free energy of activation for the slipping-on and slipping-off processes. The optical properties of the rotaxanes, including photoinduced electron transfer, were also revealed.

Original languageEnglish
Pages (from-to)1096-1101
Number of pages6
JournalOrganic Letters
Volume22
Issue number3
Early online date16 Jan 2020
DOIs
Publication statusPublished - 7 Feb 2020

Funding

This work was funded by the GW4 consortium (GW4-AF5-002), the University of Bath, and Grants-in-Aid for JSPS Fellows (JSPS KAKENHI Grant JP19J12257). Y.K. thanks the Kyushu University Leading Program for “Molecular System for Devices” from MEXT Japan. Y.K. is also grateful to Mr. Tiberiu M. Gianga and Ms. Dora M. Rasădean at the University of Bath for their great help and advice about molecular design and characterization.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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