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
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
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
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
<a href="/en/project/GA19-03160S" target="_blank" >GA19-03160S: Electrochemical study on new artificial enzymes and their role in sensing of neurotransmitters</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Electrochimica acta
ISSN
0013-4686
e-ISSN
1873-3859
Volume of the periodical
370
Issue of the periodical within the volume
FEB 2021
Country of publishing house
GB - UNITED KINGDOM
Number of pages
8
Pages from-to
137674
UT code for WoS article
000623415400009
EID of the result in the Scopus database
2-s2.0-85099311810