Chemical oxidative polymerization of ethacridine
Само за регистроване кориснике
2012
Аутори
Marjanović, BudimirJuranić, Ivan O.
Ćirić-Marjanović, Gordana
Mojović, M
Pasti, Igor
Janošević, Aleksandra
Trchova, Miroslava
Holler, P
Horský, J
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Novel electroactive paramagnetic ethacridine oligomers were synthesized by the oxidation of ethacridine lactate with ammonium peroxydisulfate in acidic aqueous solution. The oxidative coupling of ethacridine was proved by gel permeation chromatography and MALDI-TOF mass spectrometry demonstrating the presence of oligomeric chains. Theoretical study of the mechanism of oxidation of ethacridine has been based on the semi-empirical quantum chemical computations of heat of formation and ionization energy of ethacridine, protonated ethacridine, generated reactive species and reaction intermediates, taking into account influence of pH and solvation effects. It was revealed that the prevalent ethacridine dimers are N(C6)C5 coupled. The influence of oxidant to monomer mole ratio on the molecular structure and the morphology of ethacridine oligomers has been studied by elemental analysis, FTIR, Raman, EPR and UV-Visible spectroscopies, MALDI-TOF mass spectrometry and scanning electron microscop...y. Besides unoxidized monomeric units as prevalent, oligoethacridines contain the iminoquinonoid and newly formed fused phenazine units. The electroactivity of ethacridine oligomers was investigated by cyclic voltammetry.
Кључне речи:
Electroactive oligomer / Ethacridine / Functionalized oligoaminoacridine / Oxidative polymerization / ParamagnetismИзвор:
Reactive and Functional Polymers, 2012, 72, 1, 25-35Финансирање / пројекти:
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
- Електропроводни и редокс-активни полимери и олигомери: синтеза, структура, својства и примена (RS-MESTD-Basic Research (BR or ON)-172043)
- HPSEE European project
- Czech Grant Agency (203/08/0686)
DOI: 10.1016/j.reactfunctpolym.2011.10.002
ISSN: 1381-5148
WoS: 000299971700004
Scopus: 2-s2.0-80755152944
Институција/група
PharmacyTY - JOUR AU - Marjanović, Budimir AU - Juranić, Ivan O. AU - Ćirić-Marjanović, Gordana AU - Mojović, M AU - Pasti, Igor AU - Janošević, Aleksandra AU - Trchova, Miroslava AU - Holler, P AU - Horský, J PY - 2012 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1806 AB - Novel electroactive paramagnetic ethacridine oligomers were synthesized by the oxidation of ethacridine lactate with ammonium peroxydisulfate in acidic aqueous solution. The oxidative coupling of ethacridine was proved by gel permeation chromatography and MALDI-TOF mass spectrometry demonstrating the presence of oligomeric chains. Theoretical study of the mechanism of oxidation of ethacridine has been based on the semi-empirical quantum chemical computations of heat of formation and ionization energy of ethacridine, protonated ethacridine, generated reactive species and reaction intermediates, taking into account influence of pH and solvation effects. It was revealed that the prevalent ethacridine dimers are N(C6)C5 coupled. The influence of oxidant to monomer mole ratio on the molecular structure and the morphology of ethacridine oligomers has been studied by elemental analysis, FTIR, Raman, EPR and UV-Visible spectroscopies, MALDI-TOF mass spectrometry and scanning electron microscopy. Besides unoxidized monomeric units as prevalent, oligoethacridines contain the iminoquinonoid and newly formed fused phenazine units. The electroactivity of ethacridine oligomers was investigated by cyclic voltammetry. T2 - Reactive and Functional Polymers T1 - Chemical oxidative polymerization of ethacridine VL - 72 IS - 1 SP - 25 EP - 35 DO - 10.1016/j.reactfunctpolym.2011.10.002 ER -
@article{ author = "Marjanović, Budimir and Juranić, Ivan O. and Ćirić-Marjanović, Gordana and Mojović, M and Pasti, Igor and Janošević, Aleksandra and Trchova, Miroslava and Holler, P and Horský, J", year = "2012", abstract = "Novel electroactive paramagnetic ethacridine oligomers were synthesized by the oxidation of ethacridine lactate with ammonium peroxydisulfate in acidic aqueous solution. The oxidative coupling of ethacridine was proved by gel permeation chromatography and MALDI-TOF mass spectrometry demonstrating the presence of oligomeric chains. Theoretical study of the mechanism of oxidation of ethacridine has been based on the semi-empirical quantum chemical computations of heat of formation and ionization energy of ethacridine, protonated ethacridine, generated reactive species and reaction intermediates, taking into account influence of pH and solvation effects. It was revealed that the prevalent ethacridine dimers are N(C6)C5 coupled. The influence of oxidant to monomer mole ratio on the molecular structure and the morphology of ethacridine oligomers has been studied by elemental analysis, FTIR, Raman, EPR and UV-Visible spectroscopies, MALDI-TOF mass spectrometry and scanning electron microscopy. Besides unoxidized monomeric units as prevalent, oligoethacridines contain the iminoquinonoid and newly formed fused phenazine units. The electroactivity of ethacridine oligomers was investigated by cyclic voltammetry.", journal = "Reactive and Functional Polymers", title = "Chemical oxidative polymerization of ethacridine", volume = "72", number = "1", pages = "25-35", doi = "10.1016/j.reactfunctpolym.2011.10.002" }
Marjanović, B., Juranić, I. O., Ćirić-Marjanović, G., Mojović, M., Pasti, I., Janošević, A., Trchova, M., Holler, P.,& Horský, J.. (2012). Chemical oxidative polymerization of ethacridine. in Reactive and Functional Polymers, 72(1), 25-35. https://doi.org/10.1016/j.reactfunctpolym.2011.10.002
Marjanović B, Juranić IO, Ćirić-Marjanović G, Mojović M, Pasti I, Janošević A, Trchova M, Holler P, Horský J. Chemical oxidative polymerization of ethacridine. in Reactive and Functional Polymers. 2012;72(1):25-35. doi:10.1016/j.reactfunctpolym.2011.10.002 .
Marjanović, Budimir, Juranić, Ivan O., Ćirić-Marjanović, Gordana, Mojović, M, Pasti, Igor, Janošević, Aleksandra, Trchova, Miroslava, Holler, P, Horský, J, "Chemical oxidative polymerization of ethacridine" in Reactive and Functional Polymers, 72, no. 1 (2012):25-35, https://doi.org/10.1016/j.reactfunctpolym.2011.10.002 . .