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Bis-morpholine-substituted perylene bisimides: Impact of isomeric arrangement on electrochemical and spectroelectrochemical properties

Goretzki, Gudrun; Davies, E. Stephen; Argent, Stephen P.; Alsindi, Wassim Z.; Blake, Alexander J.; Warren, John E.; McMaster, Jonathan; Champness, Neil R.

Authors

Gudrun Goretzki

Wassim Z. Alsindi

Alexander J. Blake

John E. Warren

Neil R. Champness



Abstract

(Graph Presented) The synthesis and separation of the 1,6- and 1,7- isomers of N,N′-bis(n-butyl)dimorpholino-3,4:9,10-perylenetetracarboxylic acid bisimide are reported. Investigations of the electrochemical and spectroscopic, in particular, spectroelectrochemical, properties of the two isomers reveal a sequence of electrochemically and chemically reversible redox processes for both isomers. Importantly, the 1,7-isomer of N,N′-bis(n-butyl)dimorpholino-3, 4:9,10-perylenetetracarboxylic acid bisimide was observed to undergo a two-electron oxidation process, which contrasts with the behavior of both the corresponding 1,6-isomer and other related amino-substituted perylene bis-imide species. © 2008 American Chemical Society.

Citation

Goretzki, G., Davies, E. S., Argent, S. P., Alsindi, W. Z., Blake, A. J., Warren, J. E., …Champness, N. R. (2008). Bis-morpholine-substituted perylene bisimides: Impact of isomeric arrangement on electrochemical and spectroelectrochemical properties. Journal of Organic Chemistry, 73(22), 8808-8814. https://doi.org/10.1021/jo801557e

Journal Article Type Article
Acceptance Date Jul 18, 2008
Online Publication Date Oct 15, 2008
Publication Date Nov 21, 2008
Deposit Date Jul 3, 2020
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 73
Issue 22
Pages 8808-8814
DOI https://doi.org/10.1021/jo801557e
Public URL https://nottingham-repository.worktribe.com/output/3109205
Publisher URL https://pubs.acs.org/doi/10.1021/jo801557e