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.

doi:10.1021/jo400026r

Authors

Anna G. Slater

STEPHEN DAVIES e.s.davies@nottingham.ac.uk
Research Officer

STEPHEN ARGENT stephen.argent@nottingham.ac.uk
Senior Research Fellow

William Lewis

Alexander J. Blake

JONATHAN MCMASTER Jonathan.McMaster@nottingham.ac.uk
Professor of Chemistry

Neil R. Champness

Abstract

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.

Citation

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. https://doi.org/10.1021/jo400026r

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
DOI	https://doi.org/10.1021/jo400026r
Public URL	https://nottingham-repository.worktribe.com/output/3108626
Publisher URL	https://pubs.acs.org/doi/10.1021/jo400026r