Multipurpose acetic acid functionalized carbazole derivatives: Synthesis, electrochemical properties and electrochromic device applications

Özdemir Hacıoğlu, Şerife
Akbey, Tuba E.
Toppare, Levent Kamil
In this study, synthesis of two multifunctional acetic acid functionalized carbazole bearing monomers; 243,6-bis(2,3-dihydrothieno [3,4-b] [1,4]dioxin-5-yl)-9H-carbazol-9-yl)acetic acid (Ml) and 3,6-dithien-2-yl-9H car bazol-9-ylaceticacid (M2) via Stille cross-coupling reaction was reported. Obtained monomers were electro-chemically polymerized in 0.1 M TBAPF(6)/DCM/ACN (5:95, v:v) solution and characterized in terms of electrochemical, spectroelectrochemical and electrochromic switching behaviors. When poly-2-(3,6-bis(2,3-dihydrothieno[3,4-b] [1,4]dioxin-5-yl)-9H-carbazol-9-ypacetic acid (P1) and poly-3,6-dithien-2-yl-9H car bazol-9-ylaceticacid (P2) were compared in terms of electrochemical behaviors, by virtue of the electron-rich EDOT units in the P1 chains, the polymer film exhibited lower monomer oxidation potential at around 1.05 V. Both polymers exhibited neutral state yellow color with similar optical band gaps and multi-electrochromic behaviors under different applied potentials. Insertion of thiophene unit instead of ethylene dioxythiophene (EDOT) unit on the polymer backbone enhanced the electrochromic and optical contrast properties and P2 showed the higher optical contrast then P1. Furthermore, owing to the promising electrochromic properties of P2 like red shifted absorption and higher optical contrast, a prototype P2 and PEDOT bearing solid state electrochromic devices (ECDs) were constructed and characterized. P2 and PEDOT comprising ECD works between yellow and blue colors at - 2.0 V and at 2.0 V respectively, with 41% optical contrast and 1.3 s switching time at 580 nm. Furthermore, P2 was used for energy storage applications before and in the present study it was used for ECD applications with promising results which make acetic acid functionalized carbazole derivatives mull-purpose new generation materials.


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Çamurlu, Pınar; Toppare, Levent Kamil; Department of Chemistry (2006)
In this study three different 3-ester substituted thiophene monomers were synthesized via esterification reaction of 3-thiophene ethanol with adipoyl chloride or sebacoyl chloride or octanoyl chloride in the presence of triethylamine at 00C. Characterizations of the monomers were performed by 1H-NMR, 13C-NMR, FTIR, DSC, TGA techniques. Electrochemical behavior of the monomers both in presence or absence of BFEE were studied by cyclic voltammetry. Results showed the astonishing effect of BFEE on the polymeri...
Bifunctional Silicotungstic Acid and Tungstophosphoric Acid Impregnated Cu-Zn-Al & Cu-Zn-Zr Catalysts for Dimethyl Ether Synthesis from Syngas
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In the present study, a set of methanol synthesis catalysts with different Cu/Zn/Al or Cu/Zn/Zr molar ratios were synthesized by a co-precipitation method. Silicotungstic acid and tungstophosphoric acid were impregnated into these materials to synthesize new bifunctional catalytic materials to be used in direct synthesis of dimethyl ether (DME) from syngas. In the case of methanol production, synthesized Cu/Zn/Al catalysts exhibited quite high methanol selectivity, reaching to approximately 87%. These resul...
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Oguzturk, H. Esra; TİRKEŞ, SEHA; Önal, Ahmet Muhtar (2015-08-01)
In this study, synthesis of four new monomers; 3,6-di(2-furyl)-9H-carbazole (M1), 3,6-di(2-furyl)-9-ethyl-carbazole (M2), 2,7-di(2-furyl)-9-H-carbazole (M3), 2,7-di(2-furyl)-9-(tridecan-7-yl)-9H-carbazole (M4), was achieved via Stifle cross-coupling reaction. The monomers were electrochemically polymerized, via repetitive cycling in acetonitrile-tetrabutylammonium hexafluorophosphate electrolytic medium. Optical and electrochemical properties of the monomers and their corresponding polymers were investigate...
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Polyhedral oligomeric silsesquioxanes appended conjugated soluble polymers based on thieno[3,4-c]pyrrole-4,6,dione acceptor unit
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A series of new donor-acceptor-donor type fluorescent molecules incorporating thieno[3,4-c]pyrrole-4,6-dione (TPD) as the acceptor unit were synthesized. TPD acceptor unit was modified with polyhedral oligomeric silsesquioxanes (POSS) cages and integrated with thiophene and alkylenedioxythiophene derivatives (3,4-ethylenedioxythiophene (EDOT) and 3,4-propylenedioxythiophene (ProDOT)) using Stille coupling reaction. The monomers, T-2-POSS, E-2-POSS, and P-2-POSS, were polymerized successfully via electrochem...
Citation Formats
Ş. Özdemir Hacıoğlu et al., “Multipurpose acetic acid functionalized carbazole derivatives: Synthesis, electrochemical properties and electrochromic device applications,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, vol. 908, pp. 0–0, 2022, Accessed: 00, 2022. [Online]. Available: