Bis-morpholine-Substituted Perylene Bisimides: Impact of Isomeric Arrangement on Electrochemical and Spectroelectrochemical Properties
The Journal of Organic Chemistry2008Vol. 73(22), pp. 8808–8814
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Gudrun Goretzki, E. Stephen Davies, Stephen P. Argent, W.Z. Alsindi, Alexander J. Blake, Jason D. Warren, Jonathan McMaster, Neil R. Champness
Abstract
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.
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