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A Perylene Diimide Rotaxane: Synthesis, Structure and Electrochemically Driven De-Threading

DOI: 10.1002/chem.201103090 DOI Help
PMID: 22135247 PMID Help

Authors: Benjamin J. Slater (University of Nottingham) , E. Stephen Davies (University of Nottingham) , Stephen Argent (University of Nottingham) , Harriott Nowell (Diamond Light Source) , William Lewis (University of Nottingham) , Neil Champness (University of Nottingham) , Sandy Blake (University of Nottingham)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemistry - A European Journal , VOL 17 (52)

State: Published (Approved)
Published: December 2011

Abstract: The first example of a [2]-rotaxane in which a perylene diimide acts as a recognition site has been synthesised and characterised. The interlocked nature of the compound has been verified by both NMR studies and an X-ray structure determination. Electrochemical investigations confirm that the nature of the redox processes associated with the perylene diimide are modified by the complexation process and that it is possible to mono-reduce the [2]-rotaxane to give a radical anion based rotaxane. Further reduction of the compound leads to de-threading of the macrocycle from the reduced PTCDI recognition site. Our synthetic strategies confirm the potential of PTCDI-based rotaxanes as viable targets for the preparation of complex interlocked species.

Journal Keywords: Electrochemistry; Perylene Diimide; Redox Chemistry; Rotaxanes; X-Ray Structures

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 07/12/2011 10:12

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