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

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

doi:10.1021/jo801557e

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

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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	8808-8814
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	73
Issue number	22
DOIs	https://doi.org/10.1021/jo801557e
Publication status	Published - 21 Nov 2008

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10.1021/jo801557e

CCDC 713982: Experimental Crystal Structure Determination
Goretzki, G. (Contributor), Davies, E. S. (Contributor), Argent, S. P. (Contributor), Alsindi, W. Z. (Contributor), Blake, A. J. (Contributor), Warren, J. (Contributor), McMaster, J. (Contributor) & Champness, N. R. (Contributor), Cambridge Crystallographic Data Centre, 2008
DOI: 10.5517/ccryyp9, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccryyp9&sid=DataCite
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title = "Bis-morpholine-substituted perylene bisimides: Impact of isomeric arrangement on electrochemical and spectroelectrochemical properties",

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. {\textcopyright} 2008 American Chemical Society.",

author = "Gudrun Goretzki and Davies, {E. Stephen} and Argent, {Stephen P.} and Alsindi, {Wassim Z.} and Blake, {Alexander J.} and Warren, {John E.} and Jonathan McMaster and Champness, {Neil R.}",

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year = "2008",

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doi = "10.1021/jo801557e",

language = "English",

volume = "73",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Bis-morpholine-substituted perylene bisimides: Impact of isomeric arrangement on electrochemical and spectroelectrochemical properties

AU - Goretzki, Gudrun

AU - Davies, E. Stephen

AU - Argent, Stephen P.

AU - Alsindi, Wassim Z.

AU - Blake, Alexander J.

AU - Warren, John E.

AU - McMaster, Jonathan

AU - Champness, Neil R.

N1 - 22

PY - 2008/11/21

Y1 - 2008/11/21

N2 - (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.

AB - (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.

U2 - 10.1021/jo801557e

DO - 10.1021/jo801557e

M3 - Article

SN - 0022-3263

VL - 73

SP - 8808

EP - 8814

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

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

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CCDC 713982: Experimental Crystal Structure Determination

Cite this