Application of spectroelectrochemistry in elucidation of electrochemical mechanism of azoquinoline dye 2-methyl-5-[(E)-phenyldiazenyl]quinolin-8-ol
PBN-AR
Instytucja
Wydział Matematyki, Fizyki i Chemii (Uniwersytet Śląski w Katowicach)
Informacje podstawowe
Główny język publikacji
EN
Czasopismo
Electrochimica Acta (40pkt w roku publikacji)
ISSN
0013-4686
EISSN
Wydawca
PERGAMON-ELSEVIER SCIENCE LTD
DOI
URL
Rok publikacji
2018
Numer zeszytu
Strony od-do
509-516
Numer tomu
270
Liczba arkuszy
0,40
Autorzy
Pozostali autorzy
+ 5
Słowa kluczowe
EN
Azoquinoline dyes
Reduction
Oxidation
IR spectroelectrochemistry
UV–Vis spectroelectrochemistry
Streszczenia
Język
EN
Treść
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.
Cechy publikacji
original-article
Inne
System-identifier
3342900147175
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