Unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters

Abstract A detailed investigation of the energy levels of perylene-3,4,9,10-tetracarboxylic tetraethylester as a representative compound for the whole family of perylene esters was performed. It was revealed via electrochemical measurements that one oxidation and two reductions take place. The bandg...

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Autores principales:	Christian Wiebeler, Joachim Vollbrecht, Adam Neuba, Heinz-Siegfried Kitzerow, Stefan Schumacher
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/4cd6b991e369430e93a55319c01ebc67
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spelling	oai:doaj.org-article:4cd6b991e369430e93a55319c01ebc672021-12-02T16:27:50ZUnraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters10.1038/s41598-021-95551-02045-2322https://doaj.org/article/4cd6b991e369430e93a55319c01ebc672021-08-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-95551-0https://doaj.org/toc/2045-2322Abstract A detailed investigation of the energy levels of perylene-3,4,9,10-tetracarboxylic tetraethylester as a representative compound for the whole family of perylene esters was performed. It was revealed via electrochemical measurements that one oxidation and two reductions take place. The bandgaps determined via the electrochemical approach are in good agreement with the optical bandgap obtained from the absorption spectra via a Tauc plot. In addition, absorption spectra in dependence of the electrochemical potential were the basis for extensive quantum-chemical calculations of the neutral, monoanionic, and dianionic molecules. For this purpose, calculations based on density functional theory were compared with post-Hartree–Fock methods and the CAM-B3LYP functional proved to be the most reliable choice for the calculation of absorption spectra. Furthermore, spectral features found experimentally could be reproduced with vibronic calculations and allowed to understand their origins. In particular, the two lowest energy absorption bands of the anion are not caused by absorption of two distinct electronic states, which might have been expected from vertical excitation calculations, but both states exhibit a strong vibronic progression resulting in contributions to both bands.Christian WiebelerJoachim VollbrechtAdam NeubaHeinz-Siegfried KitzerowStefan SchumacherNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-11 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Christian Wiebeler Joachim Vollbrecht Adam Neuba Heinz-Siegfried Kitzerow Stefan Schumacher Unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters
description	Abstract A detailed investigation of the energy levels of perylene-3,4,9,10-tetracarboxylic tetraethylester as a representative compound for the whole family of perylene esters was performed. It was revealed via electrochemical measurements that one oxidation and two reductions take place. The bandgaps determined via the electrochemical approach are in good agreement with the optical bandgap obtained from the absorption spectra via a Tauc plot. In addition, absorption spectra in dependence of the electrochemical potential were the basis for extensive quantum-chemical calculations of the neutral, monoanionic, and dianionic molecules. For this purpose, calculations based on density functional theory were compared with post-Hartree–Fock methods and the CAM-B3LYP functional proved to be the most reliable choice for the calculation of absorption spectra. Furthermore, spectral features found experimentally could be reproduced with vibronic calculations and allowed to understand their origins. In particular, the two lowest energy absorption bands of the anion are not caused by absorption of two distinct electronic states, which might have been expected from vertical excitation calculations, but both states exhibit a strong vibronic progression resulting in contributions to both bands.
format	article
author	Christian Wiebeler Joachim Vollbrecht Adam Neuba Heinz-Siegfried Kitzerow Stefan Schumacher
author_facet	Christian Wiebeler Joachim Vollbrecht Adam Neuba Heinz-Siegfried Kitzerow Stefan Schumacher
author_sort	Christian Wiebeler
title	Unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters
title_short	Unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters
title_full	Unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters
title_fullStr	Unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters
title_full_unstemmed	Unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters
title_sort	unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/4cd6b991e369430e93a55319c01ebc67
work_keys_str_mv	AT christianwiebeler unravelingtheelectrochemicalandspectroscopicpropertiesofneutralandnegativelychargedperylenetetraethylesters AT joachimvollbrecht unravelingtheelectrochemicalandspectroscopicpropertiesofneutralandnegativelychargedperylenetetraethylesters AT adamneuba unravelingtheelectrochemicalandspectroscopicpropertiesofneutralandnegativelychargedperylenetetraethylesters AT heinzsiegfriedkitzerow unravelingtheelectrochemicalandspectroscopicpropertiesofneutralandnegativelychargedperylenetetraethylesters AT stefanschumacher unravelingtheelectrochemicalandspectroscopicpropertiesofneutralandnegativelychargedperylenetetraethylesters
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Unraveling the electrochemical and spectroscopic properties of neutral and negatively charged perylene tetraethylesters

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