One electron vs. two electron electrochemical and chemical oxidation of electron-donor substituted diketo-pyrrolo-pyrroles

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F13%3A39896191" target="_blank" >RIV/00216275:25310/13:39896191 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388955:_____/13:00394518

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.electacta.2013.05.106" target="_blank" >http://dx.doi.org/10.1016/j.electacta.2013.05.106</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.electacta.2013.05.106" target="_blank" >10.1016/j.electacta.2013.05.106</a>

Jazyk výsledku

angličtina

Název v původním jazyce

One electron vs. two electron electrochemical and chemical oxidation of electron-donor substituted diketo-pyrrolo-pyrroles

Popis výsledku v původním jazyce

Electrochemical and chemical (using FeCl3) oxidation reactions of a series of eight N,N'-dialkylated soluble diketo-pyrrolo-pyrrole dyes (DPPs) substituted by electron donating and/or electron withdrawing groups were investigated electrochemically and byUV-vis spectrometry and the results were rationalized by DFT calculations. Influence of substituents on HOMO and LUMO energies as well as on the electron transfer mechanism was followed. Destabilization of HOMO by two piperidino-substituents in 3,6-diphenyl-DPP 5 enabled to observe a potential inversion in electrochemical oxidation of this derivative, when a two-electron oxidation occurs leading directly to a dication, whereas other DPPs are oxidized first in a one-electron transfer to a radical cation. In chemical oxidation with FeCl3 the radical cation is produced by two mechanisms: either directly (standard reaction) or in the case of 5 by a comproportionation reaction of neutral molecule and its dication. Using mutual comparison of

Název v anglickém jazyce

One electron vs. two electron electrochemical and chemical oxidation of electron-donor substituted diketo-pyrrolo-pyrroles

Popis výsledku anglicky

Electrochemical and chemical (using FeCl3) oxidation reactions of a series of eight N,N'-dialkylated soluble diketo-pyrrolo-pyrrole dyes (DPPs) substituted by electron donating and/or electron withdrawing groups were investigated electrochemically and byUV-vis spectrometry and the results were rationalized by DFT calculations. Influence of substituents on HOMO and LUMO energies as well as on the electron transfer mechanism was followed. Destabilization of HOMO by two piperidino-substituents in 3,6-diphenyl-DPP 5 enabled to observe a potential inversion in electrochemical oxidation of this derivative, when a two-electron oxidation occurs leading directly to a dication, whereas other DPPs are oxidized first in a one-electron transfer to a radical cation. In chemical oxidation with FeCl3 the radical cation is produced by two mechanisms: either directly (standard reaction) or in the case of 5 by a comproportionation reaction of neutral molecule and its dication. Using mutual comparison of

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CG - Elektrochemie

OECD FORD obor

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Projekt

<a href="/cs/project/EE2.3.30.0021" target="_blank" >EE2.3.30.0021: Posílení excelentních týmů výzkumu a vývoje na Univerzitě Pardubice</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Electrochimica Acta

ISSN

0013-4686

e-ISSN

—

Svazek periodika

106

Číslo periodika v rámci svazku

nemá

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

351-359

Kód UT WoS článku

000323192400046

EID výsledku v databázi Scopus

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