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Bis-thioether-substituted perylene diimides: Structural, electrochemical, and spectroelectrochemical properties

Slater, Anna G.; Davies, E. Stephen; Argent, Stephen P.; Lewis, William; Blake, Alexander J.; McMaster, Jonathan; Champness, Neil R.


Anna G. Slater

William Lewis

Alexander J. Blake

Neil R. Champness


The synthesis and separation of the 1,6- and 1,7- isomers of N,N′-bis(alkyl)diadamantylthio-3,4,9,10-perylenetetracarboxylic acid diimide are reported. Investigations of the structural, electrochemical, spectroscopic, and spectroelectrochemical properties of the isomers reveal a sequence of electrochemically and chemically reversible reduction processes for both isomers. Three X-ray crystal structures are reported including a pair of 1,6- and 1,7-isomers demonstrating the twist of the perylene core in the solid state. Our studies thoroughly characterize the mono- and direduced states of the two isomers allowing unequivocal characterization of the reduced species by UV-vis and IR spectroscopic measurements. EPR studies also allow direct identification of the monoreduced PTCDI species and spectroscopic measurements confirm the delocalization of electronic density around the carbonyl moieties of the reduced species. © 2013 American Chemical Society.


Slater, A. G., Davies, E. S., Argent, S. P., Lewis, W., Blake, A. J., McMaster, J., & Champness, N. R. (2013). Bis-thioether-substituted perylene diimides: Structural, electrochemical, and spectroelectrochemical properties. Journal of Organic Chemistry, 78(7), 2853-2862.

Journal Article Type Article
Acceptance Date Jan 9, 2013
Online Publication Date Mar 25, 2013
Publication Date Apr 5, 2013
Deposit Date Jul 3, 2020
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 78
Issue 7
Pages 2853-2862
Public URL
Publisher URL