Novel poly(2,5-dithienylpyrrole) (PSNS) derivatives functionalized with azobenzene, coumarin and fluorescein chromophore units: spectroelectrochemical properties and electrochromic device applications

Date

2015-01-01

Author

Yigit, Deniz
Hacioglu, Serife O.
GÜLLÜ, Mustafa
Toppare, Levent Kamil

Metadata

Show full item record

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

Item Usage Stats

242
views

0
downloads

Three novel 2,5-dithienylpyrrole (SNS) derivatives containing strong chromophore units such as azobenzene, coumarin and fluorescein were synthesized to investigate the effects of chromophore substituents on the electrochemical and spectroelectrochemical properties of resulting polymers. Electrochemical and optoelectronic characteristics of the homopolymers, poly(1-(2-(4-(phenyldiazenyl)phenoxy)ethyl)-2,5di(thiophen-2-yl)-1H-pyrrole) (PTPTAz), poly(4-(2-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)ethoxy)-2H-chromen-2-one) (PTPTCo) and poly(methyl 2-(6-(2-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl) ethoxy)-3-oxo-3H-xanthen-9-yl) benzoate) (PTPTFlo), were investigated in detail. The combination of a strong chromophore pendant group with a poly(2,5-dithienylpyrrole) (PSNS) backbone significantly influences the electronic and optoelectronic behaviors of conducting polymers. PTPTAz and PTPTCo exhibited different colors in their neutral and oxidized states while PTPTFlo showed a yellow color in all states. The optical band gap (E-g) values of PTPTAz, PTPTCo and PTPTFlo films were calculated as 2.81 eV, 2.44 eV and 2.31 eV respectively. Moreover, a PTPTFlo/PEDOT based dual type solid state electrochromic device (ECD) was constructed. The ECD exhibited quite good long-term stability with reasonable optical memory performance under ambient conditions.

Subject Keywords

Anode, Optical-properties, Color, Green, Benzotriazole, 3,4-ethylenedioxythiophene, Redox, Copolymer, Polymers

URI

https://hdl.handle.net/11511/41314

Journal

NEW JOURNAL OF CHEMISTRY

DOI

https://doi.org/10.1039/c4nj02098g

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Electrochemical polymerization and characterization of polyether-substituted aniline derivatives Tirkeş, Süha; Oenal, Ahmet M. (Wiley, 2007-08-01) 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...
Electrochemical synthesis of crowned conducting polymers : nature of radical cations in polymerization and mechanism of conductivity Cihaner, Atilla; Önal, Ahmet Muhtar; Department of Chemistry (2004) 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 solvent and tetrabutylammonium tetrafluoroborate (TBABF4) or tetrabutylammonium hexafluorophosphate (TBAPF6) 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 polymers h...
Tailoring the optoelectronic properties of donor-acceptor-donor type pi-conjugated polymers via incorporating different electron-acceptor moieties Tarkuc, Simge; Udum, Yasemin Arslan; Toppare, Levent Kamil (2012-01-31) Syntheses of donor-acceptor-donor type of pi-conjugated monomers were performed to examine the effect of the acceptor units' strength on the electrochemical and optoelectrochemical properties of the resulting monomer and polymer. Palladium catalyzed Stille cross-coupling reaction of an organotin reagent with an organic electrophile was used for the synthesis of target monomers, 5,8-bis(4-hexylthiophen-2-yl)-2-(2,3-dihydrobenzo[b][1,4]clioxin-6-y1)-3-(2,3-dihydrobenzo[b][1,41dioxin-7-yl)quinoxaline (DBQHT) a...
Synergistic effect of boron containing substances on flame retardancy and thermal stability of clay containing intumescent polypropylene nanoclay composites Dogan, Mehmet; Bayramlı, Erdal (Wiley, 2011-12-01) The functions of nanoclay and three different boron containing substances, zinc borate (ZnB), borophosphate (BPO(4)), and boron silicon containing preceramic oligomer (BSi), were studied to improve the flame retardancy of polypropylene (PP)-nanoclay-intumescent system composed of ammonium polyphosphate (APP) and pentaerythritol (PER). The flame retardancy of PP composites was investigated using limiting oxygen index (LOI), UL-94 standard, thermogravimetric analysis (TGA), and cone calorimeter.
Donor-acceptor polymer electrochromes with cyan color: Effect of alkyl chain length on doping processes Celikbilek, Ozden; Icli-Ozkut, Merve; Algi, Fatih; Önal, Ahmet Muhtar; CİHANER, ATİLLA (2012-01-01) A new series of donor-acceptor-donor (D-A-D) type compounds consisting of dialkyl substituted 3,4-propylenedioxythiophene and benzothiadiazole units were synthesized and polymerized chemically and electrochemically to investigate the effect of alkyl chain length on the doping process of the conjugated polymers. It was found that the alkyl chain length plays a key role on both doping processes and the solubility of the polymer. It is also noteworthy that this new series of D-A-D electrochromes transmits or r...

Citation Formats

D. Yigit, S. O. Hacioglu, M. GÜLLÜ, and L. K. Toppare, “Novel poly(2,5-dithienylpyrrole) (PSNS) derivatives functionalized with azobenzene, coumarin and fluorescein chromophore units: spectroelectrochemical properties and electrochromic device applications,” NEW JOURNAL OF CHEMISTRY, pp. 3371–3379, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41314.