Electrochemical and optical properties of novel terthienyl based azobenzene, coumarine and fluorescein containing polymers: Multicolored electrochromic polymers

2014-01-01
Yigit, Deniz
Udum, Yasemin Arslan
GÜLLÜ, Mustafa
Toppare, Levent Kamil
Three electroactive terthienyl based monomers, namely 1-phenyl-2-[4-(2,2':5',2 ''-terthien-3'-ylmethoxy)phenyl]diazene (TTAz), 4-(2,2':5',2 ''-terthien-3'-ylmethoxy)-2H-chromen-2-one (TTCo) and methyl 2-[3-oxo-6-(2,2':5',2 ''-terthien-3'-ylmethoxy)-3H-xanthen-9-yl] benzoate (TTFlo), were synthesized with good yields and their conducting polymers were electrochemically prepared on ITO electrode surfaces. The effect of chromophore type on electrochemical and optical properties of the polymers was investigated using cyclic voltammetry and spectroelectrochemical techniques in detail. Results revealed that type of chromophore group greatly influences the electronic and optoelectronic behaviors of electrochromic materials. It was observed that PTTAz, PTTCo and PTTFlo also exhibited multicolored electrochromism at their neutral and oxidized states. Electrochromic switching studies indicated that PTTAz (28% at 500 nm, 25% at 770 nm and 64% at 1220 nm) and PTTCo (25% at 475 nm, 32% at 740 nm and 63% at 1200 nm) have higher optical contrasts (Delta T%) with longer switching times than those of PTTFlo (16% at 496 nm and 50% at 1280 nm) in both visible and NIR regions. Comparing with PTTFlo film, PTTAz and PTTCo polymer films showed more reasonable switching stabilities. Besides, the optical band gaps were calculated from the onset of pi-pi* transition in polymer's neutral states, as 1.65 eV, 1.80 eV and 1.78 eV for PTTAz, PTTCo and PTTFlo, respectively.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY

Suggestions

Electrochemical polymerization of a new low-voltage oxidized thienylenepyrrole-derivative and its electrochromic device application
Carbas, Buket Bezgin; KIVRAK, Arif; TEKE, Ecem; Zora, Metin; Önal, Ahmet Muhtar (Elsevier BV, 2014-09-01)
Synthesis of a new monomer, 2,5-bis-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1-phenyl-1H-pyrrole (ENE), from pyrrole, iodobenzene and 3,4-ethylenedioxythiophene (EDOT), and its electropolymerization are reported. ENE was oxidized at a low oxidation potential (0.45 V vs. Ag/AgCl) and successfully electropolymerized in acetonitrile containing 0.1 M NaClO4 and LiClO4 electrolyte mixture. The resulting polymer, P(ENE), revealed five distinctive colors upon doping, which indicated that the polymer is multichro...
Spectroelectrochemical investigation of the anodic oxidation of dibenzo-18-crown-6
Cihaner, A; Önal, Ahmet Muhtar (Elsevier BV, 2004-10-01)
Poly(dibenzo-18-crown-6) (poly-DB18C6) was synthesized by electrochemical oxidation of dibenzo-18-crown-6 (DB18C6) using a mixture of acetonitrile and dichloromethane as the solvent and tetrabutylammonium tetrafluoroborate (TBABF(4)) or tetrabutylammonium hexafluorophosphate (TBAPF(6)) as supporting electrolyte. The anodic polymerization of DB18C6 was investigated using in situ ESR and in situ UV-Vis spectroscopic techniques. Spectroelectrochemical (SPEL), properties and thermal analysis of the resulting po...
Dual type complementary colored polymer electrochromic devices utilized by 3-ester substituted thiophenes
CAMURLU, P; Çırpan, Ali; Toppare, Levent Kamil (Elsevier BV, 2004-10-15)
Dual type polymer electrochromic devices (ECDs) based on potentiodynamically coated films of octanoic acid 2-thiophen-3-yl-ethyl ester (OTE), decanedioic acid bis-(2-thiophen-3-yl-ethyl) ester (DATE) and ethylene dioxythiophene (EDOT) were constructed. The former two function as anodically coloring layers and the latter as a cathodically coloring layer in between tetrabutylammonium tetrafluoroborate (TBAFB) poly(methylmethacrylate) gel media. The spectroelectrochemistry, switching ability and stability of t...
Molecular architecture: Another plausible pathway toward a low band gap polymer
Tarkuc, Simge; Udum, Yasemin Arslan; Toppare, Levent Kamil (Elsevier BV, 2010-05-01)
A donor-acceptor-donor pi-conjugated monomer (10,13-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)dibenzo[a,c]phenazine (PHED)) composed of bi-EDOT and dibenzo[a,c]phenazine repeat units was synthesized to examine the role of acceptor structure on the electronic and optoelectronic properties of the polymer. The spectroelectrochemical analysis showed that the introduction of electron-accepting unit results in a shift in the onset of the pi-pi* transition towards longer wavelengths. The optical band gap (Eg) f...
Electrochemical copolymerization and characterization of dianilines linked by polyether bridge with aniline
TİRKEŞ, SEHA; Önal, Ahmet Muhtar (Springer Science and Business Media LLC, 2010-04-01)
Copolymer of aniline and triethylene glycol bis(o-aminophenyl) ether was synthesized by constant potential electrolysis. Cyclic voltammogram of the copolymer films recorded in the monomer-free electrolytic solution revealed that the redox behavior of the films approaches to that of poly(triethylene glycol bis(o-aminophenyl) ether) with increasing amount of triethylene glycol bis(o-aminophenyl) in the feed ratio. Copolymerization was investigated by in situ recording the changes in the electronic absorption ...
Citation Formats
D. Yigit, Y. A. Udum, M. GÜLLÜ, and L. K. Toppare, “Electrochemical and optical properties of novel terthienyl based azobenzene, coumarine and fluorescein containing polymers: Multicolored electrochromic polymers,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 215–222, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/36908.