Investigation of Fluorine Atom Effect on Benzothiadiazole Acceptor Unit in Donor Acceptor Donor Systems

Date

2019-07-12

Author

Çakal, Deniz
Akdağ, Akın
Önal, Ahmet Muhtar

Metadata

Show full item record

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

Item Usage Stats

232
views

0
downloads

Synthesis of two new pi-conjugated monomers containing fluorine substituted benzothiadiazoles as acceptor units and 3,4-ethylenedioxythiophene (EDOT) as donor unit was accomplished by facilitating Stille cross-coupling reactions (4,7-bis(2,3-dihydrothieno[3,4-b][1,4] dioxin-5-yl)-5-fluorobenzo[c][1,2,5] thiadiazole (E2BTD-F) and 4,7-bis(2,3-dihydrothieno [3,4-b][1,4] dioxin-5-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole (E2BTD-2F)). NMR and HRMS spectra of newly synthesized compounds are in agreement with the structures. To compare fluorine substitution effects, non-fluorinated analogue (4,7-bis(2,3-dihydrothieno[3,4-b][1,4] dioxin-5-yl) benzo[c][1,2,5] thiadiazole (E2BTD)) was also synthesized. Besides a blue shift in their absorption spectra, an anodic shift was also noted in the oxidation potentials of both monomers with fluorine atom substitution on the acceptor unit. This was further confirmed by DFT calculations such that upon fluorine substitution EDOT donor units deviate from planarity. Electropolymerization of the monomers were achieved successfully via potentiodynamic polymerization method. A similar trend in optoelectronic properties was also observed for the polymer films as for the monomers. (C) 2019 The Electrochemical Society.

Subject Keywords

Renewable Energy, Sustainability and the Environment, Electrochemistry, Materials Chemistry, Electronic, Optical and Magnetic Materials, Surfaces, Coatings and Films, Condensed Matter Physics

URI

https://hdl.handle.net/11511/47522

Journal

JOURNAL OF THE ELECTROCHEMICAL SOCIETY

DOI

https://doi.org/10.1149/2.0471912jes

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis of New Thienylene Pyrrole Monomers and Their Electropolymerizations Eken, Serap; Carbas, Buket Bezgin; Akdağ, Akın; Önal, Ahmet Muhtar (The Electrochemical Society, 2014-01-01) In this study, four new 2,5-dithienylpyrroles (SNS) 1-(3-fluoro-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-FPTP), 1-(3-chlorophenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-ClPTP), 1-(3-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-BrPTP) and 1-(4-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (p-BrPTP) containing meta and para substituted benzene ring at the nitrogen atom were synthesized via Paal-Knorr condensation of 1,4-di(2-thienyl)-1,4-butanedione with corresponding halo-substituted anilines. The mon...
Synthesis and Characterization of Thiophene and Thieno[3,2-b]thiophene Containing Conjugated Polymers Rustamh, Elvin; Goker, Seza; UDUM, YASEMİN; Udum, Yasemin Arslan; Toppare, Levent Kamil (The Electrochemical Society, 2015-01-01) Herein, we report the synthesis of two donor-acceptor-donor polymers (P1 and P2) based on thiophene (M1) and thieno [3,2-b]thiophene (M2) as the donor and 2,5-bis(dodecyloxy)benzene as the acceptor unit. The effects of different donor units on the polymers' electrochemical and optical properties were examined by cyclic voltammetry and spectroelectrochemical analysis. Introducing thieno[3,2-b]thiophene unit as the donor unit enhances pi-stacking and consequently lowering the bandgap of the resulting polymer....
Syntheses and Characterization of Benzotriazole, Thienopyrroledione, and Benzodithiophene Containing Conjugated Random Terpolymers for Organic Solar Cells Goksu, Kardelen; Hizalan, Gonul; Udum, Yasemin Arslan; Hacioglu, Serife Ozdemir; Cevher, Sevki Can; Akrema, Akrema; Toppare, Levent Kamil; Çırpan, Ali (The Electrochemical Society, 2019-11-20) Two random terpolymers bearing alkoxy-benzodithiophene as an electron-rich unit and N-octylthieno[3,4,c]pyrrole-4,6-dione (TPD) as an electron deficient group with thiophene and selenophene pi bridges, were synthesized and characterized. Electrochemical, optical properties of the polymers were analyzed to get an insight on the effect of different p bridges. Photovoltaic performances of the polymers were investigated with a conventional device architecture. PBTS, PBTSe based polymer solar cells (PSCs) exhibi...
Electrochemical Behavior of Hydrazine Borane in Methanol Solution Ozhava, Derya; Önal, Ahmet Muhtar; Özkar, Saim (The Electrochemical Society, 2014-01-01) Electrochemical behavior of hydrazine borane (HB) was investigated on gold electrode in 0.5 M LiClO4 solution in methanol using cyclic voltammetry, electrochemical impedance spectroscopy (EIS) and chronoamperometry. Two irreversible peaks at 164 and 530 mV are attributed to direct electro-oxidation of HB on gold electrode in methanol. Both EIS results and CV data at different scan rates indicate a diffusion controlled electron transfer reaction. Furthermore, the Tafel slope (b = 0.191 V) and charge transfer...
Modeling of Magnetic Properties of Nanocrystalline La-doped Barium Hexaferrite KÜÇÜK, İLKER; Sozeri, Huseyin; Ozkan, Husnu (Springer Science and Business Media LLC, 2011-05-01) In this paper an artificial neural network (ANN) has been developed to compute the magnetization of the pure and La-doped barium ferrite powders synthesized in ammonium nitrate melt. The input parameters were: the Fe/Ba ratio, La content, sintering temperature, HCl washing and applied magnetic field. A total of 8284 input data set from currently measured 35 different samples with different Fe/Ba ratios, La contents and washed or not washed in HCl were available. These data were used in the training set for ...

Citation Formats

D. Çakal, A. Akdağ, and A. M. Önal, “Investigation of Fluorine Atom Effect on Benzothiadiazole Acceptor Unit in Donor Acceptor Donor Systems,” JOURNAL OF THE ELECTROCHEMICAL SOCIETY, pp. 0–0, 2019, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47522.