Carbazole based electrochromic polymers bearing ethylenedioxy and propylenedioxy scaffolds

Önal, Ahmet Muhtar
In this study, synthesis of two new monomers; 2-(2,3-dihydrothieno[3,4-b] (1,4] dioxin-5-yl)-7(2,3-dihydrothieno [3,4-b][1,4]dioxin-7-yl)-9H-carbazole (ECzE) and 2-(3,3-dihexy1-3,4-dihydro2H-thieno[3,4-b][1,4]dioxepin-6yl)-7-(3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b] [1,4] dioxepin-8-yl)-9H-carbazole (PCzP), via Stille cross-coupling reaction and their electrochemical polymerization both by repetitive cycling and by constant potential electrolysis was reported. The electrochemical and optical properties of the monomers and their corresponding polymers, PECzE and PPCzP, were investigated and it was found that 3,4-ethylenedioxythiophene (EDOT) unit containing monomer and polymer (ECzE and PECzE) have lower oxidation potentials and lower band gap values as compared to dihexyl substituted 3,4-propylenedioxythiophene (PRODOT-6) unit containing monomer and polymer (PCzP and PPCzP). Spectroelectrochemical studies revealed that both of the polymer films exhibit multielectrochromic behavior as well as good electrochemical stability. Moreover, PPCzP was found to be soluble in some organic solvents and its solution in tetrahydrofuran can be reversibly oxidized and reduced using chemical reagents. A dual-type electrochromic device was also constructed using soluble PPCzP as the anodically coloring material and the optical studies were performed on the device. The electrochromic device showed good electrochromic response, such as reasonable coloration efficiency and redox stability.


Electrochemical synthesis of new conjugated polymers based on carbazole and furan units
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...
Alkyl end group Modification of Benzotriazole and Thiophene Containing Conjugated Polymers
Cevher, Şevki Can; Keleş, Duygu; Özdemir Hacıoğlu, Şerife; Toppare, Levent Kamil; Çırpan, Ali (null; 2016-07-21)
This study focused on modifying the alkyl‐end‐group of benzotriazole and thiophene containing conjugated polymers. Introducing a moiety with struc‐turally rigid and tendency to enhance the π‐π stacking and also absorption in the high energetic region, influence the both electronic and optic properties of the conjugated polymers. Stille cross coupling chemical polymerization method was performed to synthesize the polymer contains: benzotriazole and bisthiophene. Characterizations of polymers were done in ter...
Multipurpose acetic acid functionalized carbazole derivatives: Synthesis, electrochemical properties and electrochromic device applications
Özdemir Hacıoğlu, Şerife; YİĞİT, DENİZ; Akbey, Tuba E.; UDUM, YASEMİN; GÜLLÜ, MUSTAFA; DEPCİ, TOLGA; Toppare, Levent Kamil (2022-03-01)
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 po...
Selenophene-bearing low-band-gap conjugated polymers: tuning optoelectronic properties via fluorene and carbazole as donor moieties
Yasa, Mustafa; GÖKER, SEZA; Toppare, Levent Kamil (Springer Science and Business Media LLC, 2020-05-01)
In this study, two donor-acceptor (D-A)-type conjugated polymers, namely PQSeCz and PQSeFl, were designed and synthesized. Selenophene was incorporated as the pi-bridge and quinoxaline as an acceptor unit, while carbazole and fluorene were used as the donor units. Polymers were synthesized via palladium-catalyzed Suzuki polymerization reaction. All molecules were characterized by H-1 and C-13 NMR spectroscopy. The weight and number average molecular weights of the two polymers were determined by gel permeat...
Syntheses of conducting polymers of 3-ester substituted thiophenes and characterization of their electrochromic properties
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...
Citation Formats
E. G. C. ERGÜN and A. M. Önal, “Carbazole based electrochromic polymers bearing ethylenedioxy and propylenedioxy scaffolds,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 158–165, 2018, Accessed: 00, 2020. [Online]. Available: