Phenyl-substituted cibalackrot derivatives: Redox behavior, structure-properties relationships and in situ UV-vis/EPR-spectroelectrochemistry of radical ions

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F23%3A00573390" target="_blank" >RIV/61388955:_____/23:00573390 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/23:00573390

Výsledek na webu

<a href="https://hdl.handle.net/11104/0343850" target="_blank" >https://hdl.handle.net/11104/0343850</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.electacta.2023.142498" target="_blank" >10.1016/j.electacta.2023.142498</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Phenyl-substituted cibalackrot derivatives: Redox behavior, structure-properties relationships and in situ UV-vis/EPR-spectroelectrochemistry of radical ions

Popis výsledku v původním jazyce

Redox properties and UV–vis and EPR spectroelectrochemical behavior of cibalackrot (7,14-diphenyldiindolo[3,2,1-de:3′,2′,1′-ij][1,5]naphthyridine-6,13‑dione, 1) and its six derivatives 2 - 7 carrying two substituted phenyl rings have been examined. The dyes are of potential interest for organic electronics and singlet fission for solar energy conversion. The compounds are reduced in two reversible one-electron steps under formation of a stable primary radical anion. Oxidation yields the radical cation in a first reversible step and the second step is quasireversible. The presence of radical ions was confirmed by in situ UV–vis/EPR spectroelectrochemistry. The substituents have different influence on oxidation and on reduction, as revealed using the LFER approach and interpreted with the help of calculated energies of frontier orbitals. The observed first reduction (Ered1) and first oxidation (Eox1) potentials correlate well with the calculated values and their difference (ΔE1) has photophysical relevance because it reflects the energy of HOMO-LUMO gap.

Název v anglickém jazyce

Phenyl-substituted cibalackrot derivatives: Redox behavior, structure-properties relationships and in situ UV-vis/EPR-spectroelectrochemistry of radical ions

Popis výsledku anglicky

Redox properties and UV–vis and EPR spectroelectrochemical behavior of cibalackrot (7,14-diphenyldiindolo[3,2,1-de:3′,2′,1′-ij][1,5]naphthyridine-6,13‑dione, 1) and its six derivatives 2 - 7 carrying two substituted phenyl rings have been examined. The dyes are of potential interest for organic electronics and singlet fission for solar energy conversion. The compounds are reduced in two reversible one-electron steps under formation of a stable primary radical anion. Oxidation yields the radical cation in a first reversible step and the second step is quasireversible. The presence of radical ions was confirmed by in situ UV–vis/EPR spectroelectrochemistry. The substituents have different influence on oxidation and on reduction, as revealed using the LFER approach and interpreted with the help of calculated energies of frontier orbitals. The observed first reduction (Ered1) and first oxidation (Eox1) potentials correlate well with the calculated values and their difference (ΔE1) has photophysical relevance because it reflects the energy of HOMO-LUMO gap.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10405 - Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)

Projekt

<a href="/cs/project/GA19-22806S" target="_blank" >GA19-22806S: Singletové štěpení: redox vlastnosti a fotofyzika kaptodativních biradikáloidů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

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

1873-3859

Svazek periodika

458

Číslo periodika v rámci svazku

AUG 2023

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

142498

Kód UT WoS článku

001007490900001

EID výsledku v databázi Scopus

2-s2.0-85156225702