The effects of 4,7-di(pyrrolidin-1-yl) substituents on the reduction and oxidation mechanisms of 1,10-phenanthrolines: New perspectives in tailoring of phenantroline derivatives

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F21%3A00541424" target="_blank" >RIV/61388955:_____/21:00541424 - isvavai.cz</a>

Výsledek na webu

<a href="http://hdl.handle.net/11104/0318983" target="_blank" >http://hdl.handle.net/11104/0318983</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.electacta.2020.137674" target="_blank" >10.1016/j.electacta.2020.137674</a>

Jazyk výsledku

angličtina

Název v původním jazyce

The effects of 4,7-di(pyrrolidin-1-yl) substituents on the reduction and oxidation mechanisms of 1,10-phenanthrolines: New perspectives in tailoring of phenantroline derivatives

Popis výsledku v původním jazyce

The oxidation and reduction mechanisms of substituted 4,7-di(pyrrolidin-1-yl)-1,10-phenanthrolines were investigated in non-aqueous environment by means of cyclic voltammetry. Reduction of these derivatives leads to the formation of radical anion and subsequent reductive cleavage of pyrrolidine-1-yl moiety in overall ECE reduction processes. The regenerating formation of 1,10-phenanthroline was observed. IR spectroelectrochemistry and HPLC-MS/MS analysis were applied to support this result. The presence of pyrrolidine-1-yl moiety significantly thermodynamically facilitates the reduction of the 1,10phenanthroline structure. Concerning oxidation, the primarily formed cation radical on nitrogen of the pyrrolidine moiety is further oxidized and undergoes a coupled nucleophilic addition of water and hydroxylated compound is formed as the oxidation product. Additionally, further opening of pyrrolidine ring and oxidative cleavage of alkyl are other proposed reactions. The results presented in this work pave the way for novel chelating agents with electrochemically controlled polarity. Furthermore, reductive regeneration of individual components of the molecular assemblies described in this work opens new directions in electrochemical technologies for the environmental protection.

Název v anglickém jazyce

The effects of 4,7-di(pyrrolidin-1-yl) substituents on the reduction and oxidation mechanisms of 1,10-phenanthrolines: New perspectives in tailoring of phenantroline derivatives

Popis výsledku anglicky

The oxidation and reduction mechanisms of substituted 4,7-di(pyrrolidin-1-yl)-1,10-phenanthrolines were investigated in non-aqueous environment by means of cyclic voltammetry. Reduction of these derivatives leads to the formation of radical anion and subsequent reductive cleavage of pyrrolidine-1-yl moiety in overall ECE reduction processes. The regenerating formation of 1,10-phenanthroline was observed. IR spectroelectrochemistry and HPLC-MS/MS analysis were applied to support this result. The presence of pyrrolidine-1-yl moiety significantly thermodynamically facilitates the reduction of the 1,10phenanthroline structure. Concerning oxidation, the primarily formed cation radical on nitrogen of the pyrrolidine moiety is further oxidized and undergoes a coupled nucleophilic addition of water and hydroxylated compound is formed as the oxidation product. Additionally, further opening of pyrrolidine ring and oxidative cleavage of alkyl are other proposed reactions. The results presented in this work pave the way for novel chelating agents with electrochemically controlled polarity. Furthermore, reductive regeneration of individual components of the molecular assemblies described in this work opens new directions in electrochemical technologies for the environmental protection.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GA19-03160S" target="_blank" >GA19-03160S: Elektrochemická studie nových umělých enzymů a jejich role v analýze neurotransmiterů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2021

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

370

Číslo periodika v rámci svazku

FEB 2021

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

137674

Kód UT WoS článku

000623415400009

EID výsledku v databázi Scopus

2-s2.0-85099311810