Abstract
This work is devoted to the electrochemical characterization of a new azulene compound (Z)-5-[(azulen-1-yl)methylene]-2-thioxothiazolidin-4-one (L) by cyclic, differential pulse, and rotating disk electrode voltammetries (CV, DPV and RDE, respectively). The redox processes in acetonitrile solutions are established, analyzed and some of them have been assigned to the particular functional groups at which they take place. The influence of L concentration, scan rate and scan domain in CV, and rotation rate in RDE, have been studied. Formation of a polyazulene film has been observed in millimolar solutions of L in 0.1 mol·L−1 tetrabutylammonium perchlorate in acetonitrile by successive scans in the domain of the first anodic process or by controlled potential electrolysis. Evidence for the films was obtained by electrochemistry through transfer of the modified electrodes in ferrocene solutions. The best conditions for the film synthesis (electropolymerization potential and charge) have been established. The SEM images allowed the characterization of the polyL films morphology under the conditions established for film deposition.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Razus, A.C., Birzan, Nae L., Cristian, S., Chiraleu, L.F., Cimpeanu, V.: Azulene-1-azopyridine 1′-oxides. Dyes Pigm. 57, 223–233 (2003)
Razus, A.C., Birzan, L., Cristea, M., Tecuceanu, V., Blanariu, L., Enache, C.: Novel mono- and bis-azo dyes containing the azulen-1-yl moiety: synthesis, characterization, electronic spectra and basicity. Dyes Pigm. 80, 337–342 (2009)
Razus, A.C., Birzan, L., Cristea, M., Tecuceanu, V., Hanganu, A., Enache, C.: 4-(Azulen-1-yl) six-membered heteroaromatics substituted with thiophen-2-yl or furan-2-yl moieties in 2 and 6 positions. J. Heterocycl. Chem. 48, 1019–1027 (2011)
Razus, A.C., Nica, S., Cristian, L., Raicopol, M., Birzan, L., Dragu, A.E.: Synthesis and physico-chemical properties of highly conjugated azo-aromatic systems. 4-(Azulen-1-yl)-pyridines with mono- and bis azo-aromatic moieties at C3-position of azulene. Dyes Pigm. 91, 55–61 (2011)
Razus, A.C., Birzan, L., Cristea, M., Popa, B.: Aromatic diazenes containing azulen-1-yl moieties Part 2: the synthesis, characterization, electronic spectra and basicity of novel, bis aromatic diazenes containing two azulen-1-yl moieties. Dyes Pigm. 82, 216–225 (2009)
Ungureanu, E.-M., Buica, G.-O., Razus, A.C., Birzan, L., Weisz, R., Bujduveanu, M.-R.: Electrochemical study on 4-(azulen-1-yl)-2,6-bis(2-furyl)- and 4-(azulen-1-yl)-2,6-bis(2-thienyl)-pyridines. Rev. Chim. 63(1), 27–33 (2012)
Ungureanu, E.M., Cretu, M.-S., Buica, G.-O., Razus, A., Birzan, L.: Electrochemical study of azo-azulene compounds. Electrochim. Acta. 53, 7089–7099 (2008)
Ungureanu, E.-M., Amarandei, C.A., Caval, D.I., Buica, G.O., Razus, A.C., Birzan, L.: Electrochemical synthesis of azo azulene films. J. Optoelectron. Adv. Mater. 12, 1805–1810 (2010)
Lash, T.D., Colby, D.A., Graham, S.R., Ferrence, G.M., Szczpura, L.F.: Organometallic chemistry of azuliporphyrins: synthesis, spectroscopy, electrochemistry and structural characterization of nickel(II), palladium(II) and platinum(II) complexes of azuliporphyrins. Inorg. Chem. 42, 7326–7338 (2003)
Wang, F., Lai, Y.-H., Han, M.-Y.: Stimuli-responsive conjugated copolymers having electro-active azulene and bithiophene units in the polymer skeleton: effect of protonation and p-doping on conducting properties. Macromolecules. 37, 3222–3230 (2004)
Razus, A.C., Nitu, C., Tecuceanu, V., Cimpeanu, V.: 2-Substituted (azulen-1-yl)ethenes. Eur. J. Org. Chem. 23, 4601–4610 (2003)
Sheehan, D., Hrapchak, B.: Theory and practice of Histotechnology, 2nd edn, p. 230. Battelle Press, Ohio (1980)
Emanuele, P., Goodman, Z.D.: A simple and rapid stain for copper in liver tissue. Ann. Diagn. Pathol. 2, 125–126 (1998)
Lichtenstein, I.E.: Improved rhodanine method for the spectrophotometric determination of gold. Anal. Chem. 47, 465–468 (1975)
Gilbert, H.A., Narang, D.: Spectrophotometric determination of palladium(II) with 5(p-dimethylaminobenzylidene)rhodanine. Anal. Chim. Acta 24, 241–249 (1961)
Rastegararzadeh, S., Pourreza, N., Kiasat, A.R., Yahyavi, H.: Selective solid phase extraction of palladium by adsorption of its 5 (p-dimethylaminobenzylidene) rhodanine complex on silica–PEG as a new adsorbent. Microchim. Acta 170, 135–140 (2010)
Ludlow, J.W., Guikema, J.A., Consigli, R.A.: Use of 5-(4-dimethylaminobenzylidene)rhodanine in quantitating silver grains eluted from autoradiograms of biological material. Anal. Biochem. 154, 104–109 (1986)
Kshirsagar, V., Gandhe, S., Gautam, M.D.: Electrochemical studies on p-dimethylaminobenzylidine rhodanine and its application as amperometric reagent. RASAYAN J. Chem. 3, 772–776 (2010)
Yavuz, E., Tokalioglu, S., Sahan, S.: FAAS determination of Ag(I) in water, anode slime, rock and cream samples by solid phase extraction method based on sepabeads SP207/5-(p-dimethylaminobenzylidene) rhodanine combination. J. Braz. Chem. Soc. 24, 736–742 (2013)
Fahmy, H.M., Abdul-Wahab, M., Abdel-Reheem, H.: Electrochemical reduction of some rhodanine derivatives at the DME. J. Electroanal. Chem. Interfacial. Electrochem. 184, 135–145 (1985)
Acknowledgments
The authors are grateful to Dr. A.C. Razus from the Romanian Academy, Organic Chemistry Center “C.D. Nenitzescu” for fruitful scientific advice and synthesis of the azulene derivative and to the financial support from project ID PN-II-PT-PCCA-2013-4-2151, contract number 236/2014.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Diacu, E., Buica, GO., Chilibon, I. et al. Chemically Modified Electrodes Based on 5-(Azulen-1-yl)methylene)-2-thioxothiazolidin-4-one. J Solution Chem 45, 1588–1597 (2016). https://doi.org/10.1007/s10953-016-0521-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10953-016-0521-7