Application of spectroelectrochemistry in elucidation of electrochemical mechanism of azoquinoline dye 2-methyl-5-[(E)-phenyldiazenyl]quinolin-8-ol

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F18%3A00490125" target="_blank" >RIV/61388955:_____/18:00490125 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.electacta.2018.03.096" target="_blank" >http://dx.doi.org/10.1016/j.electacta.2018.03.096</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.electacta.2018.03.096" target="_blank" >10.1016/j.electacta.2018.03.096</a>

Result language

angličtina

Original language name

Application of spectroelectrochemistry in elucidation of electrochemical mechanism of azoquinoline dye 2-methyl-5-[(E)-phenyldiazenyl]quinolin-8-ol

Original language description

In situ spectroelectrochemical detection of reaction intermediates was used as a decisive method for elucidation of a rather complex redox mechanism of azoquinoline dye 2-methyl-5-[(E)-phenyldiazenyl]quinolin-8-ol (R-N=N-Ph, where Ph = phenyl, R = 2-methyl-8-hydroxyquinoline fragment). Electrochemical properties were studied in non-aqueous solution by cyclic voltammetry, UV–Vis and IR spectroelectrochemistry and high pressure liquid chromatography with diode array detector. Oxidation and reduction mechanisms involve coupled electron and proton transfers. Oxidation proceeds primarily on hydroxyl group at quinoline moiety and (E)-5-(phenyldiazenyl)quinoline-7,8-diol as the main oxidation product has been suggested. The electrochemically active site for reduction is the azo group. This was proved by in situ UV–Vis and IR spectroelectrochemical data. Detailed analysis of the effects of the presence of acids and bases evidenced the presence of two species in equilibrium: HOR(NH + )-N=N-Ph and HOR-N=N-Ph. The compound containing the hydrazo group (5-(2-phenylhydrazinyl)quinolin-8-ol (R-N=N-Ph) is the main reduction product. Molecular orbital calculations and DFT calculations of IR spectra support the experimental results. In situ IR spectroelectrochemical experiments proved that no reaction of R-N=N-Ph anion or dianion with the solvent acetonitrile was observed during the reduction of the azodye.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10406 - Analytical chemistry

Project

<a href="/en/project/GA18-04682S" target="_blank" >GA18-04682S: Probing Electron Transport Mechanism in Single Molecule Junctions by Conductance and Thermoelectricity Measurements.</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2018

Confidentiality

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

Name of the periodical

Electrochimica acta

ISSN

0013-4686

e-ISSN

—

Volume of the periodical

270

Issue of the periodical within the volume

APR 2018

Country of publishing house

GB - UNITED KINGDOM

Number of pages

8

Pages from-to

509-516

UT code for WoS article

000429262900058

EID of the result in the Scopus database

2-s2.0-85044172029