Electrochemical and spectroelectrochemical investigations of perylene peri-tetracarbonyl species

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Electrochemical and spectroelectrochemical investigations of perylene peri-tetracarbonyl species. / Pearce, Nicholas; Davies, E. Stephen; Champness, Neil R.

In: Dyes and Pigments, Vol. 183, 108735, 23.07.2020.

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@article{824b5310756c4fa5984c4e213ca565b3,
title = "Electrochemical and spectroelectrochemical investigations of perylene peri-tetracarbonyl species",
abstract = "The electronic effects of varying the nature of the carbonyl groups in a series of perylene-3,4,9,10-tetracarbonyl compounds have been investigated. The four carbonyl groups comprise of esters, imides and anhydrides and combinations thereof. The series has been extensively characterised by electrochemical methods and it is found that the combination of imide and anhydride groups enhances the electron accepting properties of the perylene core. In contrast, the perylene core is the most electron rich when each of the four peri-positions is functionalised with an ester group. In the case of tetra-esterified perylene a reversible oxidation process can also be observed. The nature of the carbonyl species provides a degree of redox potential tunability whilst maintaining similar optical properties of the chromophores. This suggests that careful selection of peri-substituents is important in the fabrication of optoelectronic devices incorporating 3,4,9,10-tetracarbonyl perylene species.",
keywords = "Anhydrides, Electrochemistry, Electron acceptor, Esters, LUMO energy, Perylene imides, Spectroelectrochemistry",
author = "Nicholas Pearce and Davies, {E. Stephen} and Champness, {Neil R.}",
note = "Funding Information: NRC gratefully acknowledges the support of the UK Engineering and Physical Sciences Research Council ( EP/S002995/1 and EP/N033906/1 ) and that of University of Nottingham Propulsion Futures Beacon . Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",
year = "2020",
month = jul,
day = "23",
doi = "10.1016/j.dyepig.2020.108735",
language = "English",
volume = "183",
journal = "Dyes and Pigments",
issn = "0143-7208",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Electrochemical and spectroelectrochemical investigations of perylene peri-tetracarbonyl species

AU - Pearce, Nicholas

AU - Davies, E. Stephen

AU - Champness, Neil R.

N1 - Funding Information: NRC gratefully acknowledges the support of the UK Engineering and Physical Sciences Research Council ( EP/S002995/1 and EP/N033906/1 ) and that of University of Nottingham Propulsion Futures Beacon . Publisher Copyright: © 2020 Elsevier Ltd

PY - 2020/7/23

Y1 - 2020/7/23

N2 - The electronic effects of varying the nature of the carbonyl groups in a series of perylene-3,4,9,10-tetracarbonyl compounds have been investigated. The four carbonyl groups comprise of esters, imides and anhydrides and combinations thereof. The series has been extensively characterised by electrochemical methods and it is found that the combination of imide and anhydride groups enhances the electron accepting properties of the perylene core. In contrast, the perylene core is the most electron rich when each of the four peri-positions is functionalised with an ester group. In the case of tetra-esterified perylene a reversible oxidation process can also be observed. The nature of the carbonyl species provides a degree of redox potential tunability whilst maintaining similar optical properties of the chromophores. This suggests that careful selection of peri-substituents is important in the fabrication of optoelectronic devices incorporating 3,4,9,10-tetracarbonyl perylene species.

AB - The electronic effects of varying the nature of the carbonyl groups in a series of perylene-3,4,9,10-tetracarbonyl compounds have been investigated. The four carbonyl groups comprise of esters, imides and anhydrides and combinations thereof. The series has been extensively characterised by electrochemical methods and it is found that the combination of imide and anhydride groups enhances the electron accepting properties of the perylene core. In contrast, the perylene core is the most electron rich when each of the four peri-positions is functionalised with an ester group. In the case of tetra-esterified perylene a reversible oxidation process can also be observed. The nature of the carbonyl species provides a degree of redox potential tunability whilst maintaining similar optical properties of the chromophores. This suggests that careful selection of peri-substituents is important in the fabrication of optoelectronic devices incorporating 3,4,9,10-tetracarbonyl perylene species.

KW - Anhydrides

KW - Electrochemistry

KW - Electron acceptor

KW - Esters

KW - LUMO energy

KW - Perylene imides

KW - Spectroelectrochemistry

UR - http://www.scopus.com/inward/record.url?scp=85089422939&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2020.108735

DO - 10.1016/j.dyepig.2020.108735

M3 - Article

AN - SCOPUS:85089422939

VL - 183

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 108735

ER -