Designing a Solution Processable Poly(3,4-ethylenedioxyselenophene) Analogue

Date

2018-11-13

Author

Ertan, Salih
CİHANER, ATİLLA

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

26
views

0
downloads

A new derivative (EDOS-POSS) of 3,4-ethylenedioxyselenophene integrated with alkyl-substituted polyhedral oligomeric silsesquioxane (POSS) cage was synthesized and characterized. The electroactive monomer was successfully polymerized via both chemical and electrochemical methods. The obtained polymer called PEDOS-POSS was solution-processable and soluble in common organic solvents like tetrahydrofuran, toluene, dichloromethane, and chloroform. PEDOS-POSS polymer exhibited electrochromic behavior: pure blue when neutralized and highly transparent when oxidized. When compared to the parent PEDOS (1.40 eV with lambda(max) = 673 nm), PEDOS-POSS polymer film has a somewhat higher band gap (1.50 eV with lambda(max) = 668 and 724 nm). Also, PEDOS POSS exhibited high optical contrast ratio (59%) and coloration efficiency (593 cm(2)/C for 95% switching) with a low switching time (0.7 s) due to the presence of POSS cage in the polymer backbone. In addition, PEDOS-POSS polymer film was highly robust and stable under ambient conditions (without purging the electrolyte solution with inert gas). Polymer films demonstrated high electrochemical stability; for example, it retained 76% of its electroactivity after 5000 cycles. Furthermore, the polymers exhibited fluorescent properties and exhibited a reddish orange emission centered about at 640 nm. Based on the findings, to the best of our knowledge, it can be concluded that the polymers are the first examples of soluble and fluorescent PEDOS derivatives. These promising properties make PEDOS-POSS polymer a potential material for bioapplications like imaging the cancer cells as well as optoelectronic applications.

Subject Keywords

Inorganic Chemistry, Organic Chemistry, Materials Chemistry, Polymers and Plastics

URI

https://hdl.handle.net/11511/65791

Journal

MACROMOLECULES

DOI

https://doi.org/10.1021/acs.macromol.8b01833

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Understanding the influence of hydrogen bonding and diisocyanate symmetry on the morphology and properties of segmented polyurethanes and polyureas: Computational and experimental study Sami, Selim; Yıldırım, Erol; Yurtsever, Mine; Yurtsever, Ersin; Yilgor, Emel; Yilgor, Iskender; Wilkes, Garth L. (Elsevier BV, 2014-09-02) Quantum mechanical calculations (QMC) and dissipative particle dynamics (DPD) siniulations were utilized to understand the nature of the short and long-range hydrogen bonding and its influence on the microphase morphology in segmented polyurethanes and segmented polyureas prepared without chain extenders through the stoichiometric reactions of hydroxy or amine terminated poly(tetramethylene oxide) (PTMO-1000) with 1,4-phenylene diisocyanate (PPDI) and 1,3-phenylene diisocyanate (MPDI). The possibility of lo...
ELECTROINITIATED POLYMERIZATION OF ACRYLAMIDE BY DIRECT ELECTRON-TRANSFER 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...
Coupling of ferrocenyl chromium carbene complex with cyclobutenediones Zora, Metin; Bekir Peynircioglu, N. (Elsevier BV, 2002-08-15) The coupling of ferrocenyl chromium carbene complex with cyclobutenediones leads to ferrocenyl-substituted 5-alkylidenefuranones and 4-cyclopentene-1,3-diones, methyl ferrocenoate and acetylferrocene in varying amounts. The scope and limitations of these processes are investigated. In comparison with the phenyl analog, ferrocenyl chromium carbene complex has been found to be less reactive. This is also supported by PM3 calculations. The coupling of ferrocenyl chromium carbene complex with cyclobutenediones...
Efficient one-pot synthesis of cyanoferrocene from ferrocenecarboxaldehyde using NH2OH center dot HCl/KI/ZnO/CH3CN system KIVRAK, Arif; Zora, Metin (Elsevier BV, 2007-05-01) A new and efficient one-pot synthesis of cyanoferrocene from ferrocenecarboxaldehyde is described by employing the NH2OH center dot HCI/KI/ZnO/CH3CN system.
Tuning of the neutral state color of the pi-conjugated donor-acceptor-donor type polymer from blue to green via changing the donor strength on the polymer Tarkuc, Simge; Udum, Yasemin Arslan; Toppare, Levent Kamil (Elsevier BV, 2009-07-17) Two donor-acceptor-donor types of T-conjugated monomers were synthesized using Stille coupling reaction. Both monomers were found to produce electroactive polymers upon electrochemical oxidation. The effects of different donor substituents on the polymers' electrochemical and spectroelectrochemical properties were examined. Optical characterization revealed that the band gaps of poly(2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)-5,8-di(thiophen-2-yl)quinoxaline) (PDBQTh) an...

Citation Formats

S. Ertan and A. CİHANER, “Designing a Solution Processable Poly(3,4-ethylenedioxyselenophene) Analogue,” MACROMOLECULES, pp. 8698–8704, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/65791.