ProTOT: Synthesis of the missing member of the 3,4-chalcogen substituted bridged thiophenes and its utilization in donor-acceptor polymers

Yaylali, Figen V.
Ozel, Hande
Toppare, Levent Kamil
Soylemez, Saniye
© 2020 Elsevier LtdSynthesis of sulfur containing derivatives of bridged dioxythiophene based polymers (PEDOT and PProDOT) and their applications in electrochromism have been pursued in recent years with promising results. Interestingly, synthesis of 3,4-dihydro-2H-thieno[3,4-b][1,4]oxathiepine (ProTOT) has not been pursued. Here, we describe the synthesis of this novel electron rich monomer and D-A-D type monomer that contain ProTOT as the donor and benzo[c][1,2,5]thiadiazole as the acceptor. ProTOT cannot be electrochemically polymerized to yield the corresponding polymer PProTOT. However, the D-A-D monomer utilizing ProTOT as the donor unit was electropolymerized successfully to yield P(ProTThia) and its electrochromic properties and performance in amperometric biosensors have been investigated. P(ProTThia) was shown to be both p and n-dopable with 4 distinctly different colors at different redox states. P(ProTThia) showed a promising optical contrast of 35% in the visible region and excellent optical contrast of 80% in the NIR region. A novel amperometric biosensor for the detection of glucose consisting of P(ProTThia), chitosan (CHIT) and multi-walled carbon nanotubes (MWCNT) was also constructed. Herein, for the first time, we propose that a specific combination of this trio can be used as an inexpensive alternative and effective way to fabricate highly sensitive and fast response glucose biosensors. The proposed glucose sensing system possessed superior properties with KMapp value of 0.05 mM, 32 μM limit of detection and 63.76 μA mM−1 cm−2 sensitivity which was also tested with a commercial beverage sample to ratify the feasibility of the proposed sensor.


HACIOGLU, B; Akbulut, Ural; Toppare, Levent Kamil (Wiley, 1989-10-01)
Electroinitiated polymerization of acrylamide was carried out in acetonitrile–tetrabutylammonium fluoroborate by electrolytic reduction of monomer. It was shown by cyclic voltammetry that direct electron transfer from the cathode to the monomer can be achieved in this solvent–electrolyte system. Reduction peak potentials measured by cyclic voltammetry indicated that sodium salts will interfere with such a mechanism. Since the reduction peak potential of sodium salt and dimethylformamide are found to be lowe...
YURTSEVER, E; ISSEVER, S (Elsevier BV, 1992-01-01)
Two-dimensional Monte-Carlo simulations of lattice polymers were carried out employing Lennard-Jones (LJ) type intramolecular interactions. The shape-dependent properties of these polymers were studied over a large range of interaction parameters and temperatures. The variation of the critical constant was also analysed. Two-dimensional surfaces of sections were used to determine the portions of the parameter space which corresponded to theta-conditions. The behaviour of LJ polymers far from theta-condition...
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A novel selenophene-based monomer, 1,4-di(selenophen-2-yl)-benzene (DSB), was synthesized via Stille coupling reaction of 1,4-dibromobenzene and tributyl(2-selenophenyl)stannane. Conducting polymer (PDSB) was prepared electrochemically in the presence of tetrabutylammonium hexafluorophosphate (TBAPF(6)) as the supporting electrolyte in dichloromethane (DCM). The resulting conducting polymer was characterized by Cyclic Voltammetry, Fourier Transform Infrared and Ultraviolet-visible spectroscopy. Spectroelect...
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New compounds consisting of aniline units linked by polyether bridges have been synthesized and their electrochemical polymerization was performed via constant potential electrolysis and cyclic voltammetry in an aqueous solution containing 3.0 moI L-1 H2SO4. Chemical polymerization was carried out using (NH4)(2)S2O8 as oxidizing agent. It was found that both methods gave the same polymer product without any cleavage of the polyether bridge between aniline rings. The polymers were characterized using the Fou...
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In this study, two new benzotriazole (BTz) and dithienothiophene (DTT) containing conjugated polymers were synthesized. After successful characterizations of the monomers by proton-nuclear magnetic resonance (1H NMR) and carbon-NMR (13C NMR) techniques, poly(4-(dithieno[3, 2-b:2,3-d]thiophen-2-yl)-2-(2-octyldodecyl)-2H-benzo[d][1,2,3] triazole) P1 and poly(4-(5-(dithieno[3,2-b:2,3-d]thiophen-2-yl)thiophen-2-yl)-2-(2-octyldodecyl)-7-(thiophen-2-yl)-2H-benzo[d][1,2,3]triazole) P2 were synthesized via a typica...
Citation Formats
F. V. Yaylali, H. Ozel, Y. UDUM, L. K. Toppare, S. Soylemez, and E. G. GÜNBAŞ, “ProTOT: Synthesis of the missing member of the 3,4-chalcogen substituted bridged thiophenes and its utilization in donor-acceptor polymers,” Polymer, pp. 0–0, 2020, Accessed: 00, 2021. [Online]. Available: