Design, synthesis and electropolymerization of a new chemiluminescent terthienyl system

Atılgan, Nurdan
A novel monomer, possessing chemiluminescence properties, 5,7-di-ethylenedioxythiophen-2-yl-2,3-dihydro-thieno[3,4-d]pyridazine-1,4-dione (ETE-Lum) was synthesized. Chemiluminescence properties of ETE-Lum were investigated in alkaline water solution in the presence of H2O2 and this reaction was catalyzed by Fe+3 ion and blood. This study submits a new opportunity to investigate forensic and analytical application instead of 5-amino-2,3-dihydro-1,4-phthalazine-dione (luminol). Response of other metalic cations was also investigated under the same reaction conditions. Electrochemical properties of ETE-Lum were studied in 0.1 M acetonitrile/tetrabutylammonium perchlorate solvent system containing BF3-Et2O and also in neat BF3-Et2O solution. In addition, the corresponding polymer film of ETE-Lum (PETE-Lum) was synthesized successfully via repetitive cycling by cyclic voltammetry and its electrochemical properties were investigated in a monomer-free electrolyte solution. Spectroelectrochemical behavior of the polymer film on indium tin oxide working electrode was also investigated by recording the electronic absorption spectra, in-situ, in monomer-free electrolyte solution at different potentials. Furthermore, spectroelectrochemical studies revealed that PETE-Lum had an electronic band gap of 1.66 eV. The results of electrochemical and electroluminesence measurements indicated that chemiluminecent unit of monomer was protected during polymerization. In addition, PETE-Lum film was found to be electrochemiluminescence active, maintaining its activitiy over 1000 cycles.


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A novel electroactive monomer 5,8-Di(1H-pyrrol-2-yl)-2, 3-di(thiophen-2-yl) quinoxaline (PTQ) was successfully synthesized via Stille Coupling reaction between quinoxaline and pyrrole. Nuclear magnetic resonance (1H NMR and 13C NMR) and Mass spectroscopy were used to characterize the monomer. The monomer was electrochemically polymerized in the presence of tetrabutylammonium perchlorate (TBAP) as supporting electrolyte in dichloromethane. Monomer reveals relatively low oxidation potential at +0.70V. Spectro...
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Reboxetine (RBX) electrochemical redox behavior at hanging mercury drop (HMDE) and glassy carbon electrodes (GCE) was studied in various pH Britton-Robinson universal buffers using cyclic voltammetry and square-wave voltammetry. RBX was reduced at the HMDE and oxidized at the GCE with reversible adsorption controlled and irreversible diffusion controlled processes respectively. The anodic peak is due to the amine and the cathodic peak may correspond to oxygen protonation. An oxidation reaction mechanism is ...
Citation Formats
N. Atılgan, “Design, synthesis and electropolymerization of a new chemiluminescent terthienyl system,” M.S. - Master of Science, Middle East Technical University, 2008.