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.

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., McMaster, J., & 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