Incorporation of Different Conjugated Linkers into Low Band Gap Polymers Based on 5,6-Bis(octyloxy)-2,1,3 benzooxadiazole for Tuning Optoelectronic Properties

Goker, SEZA
Udum, Yasemin Arslan
Çırpan, Ali
Toppare, Levent Kamil
Four new 2,1,3-benzooxadiazole-based donoracceptor conjugated polymers, namely poly{9-(9-heptadecanyl)-9H-carbazole-alt-5,6-bis(octyloxy)-4,7-di(selenophen-2-yl)benzo[ c][1,2,5] oxadiazole)}(PSBSC), poly{9-(9-heptadecanyl)-9H-carbazole- alt-5,6-bis(octyloxy)-4,7-di(furan-2-yl) benzo[c][1,2,5]oxadiazole)}(PFBFC), poly{9,9-dioctyl-9H-fluorene-alt-5,6bis( octyloxy)-4,7-di(selenophen-2-yl) benzo[c][1,2,5] oxadiazole)} (PSBSFL), and poly{9,9-dioctyl-9H-fluorene-alt-5,6-bis(octyloxy)- 4,7-di(furan-2-yl) benzo[c][1,2,5] oxadiazole)}(PFBFFL), were synthesized via Stille polycondensation reaction. All polymers were found to be soluble in common organic solvents such as chloroform, tetrahydrofuran, and chlorobenzene. Their structures were verified by 1 H-NMR and the molecular weights were determined by gel permeation chromatography (GPC). The polymer films exhibited broad absorption bands. Among all polymers, photovoltaic cells based on the device structure of ITO/PEDOT: PSS/PSBSC: PC71BM(1: 3, w/w)/LiF/Al revealed an open-circuit voltage of 0.62 V, a short circuit current of 7.63 mA cm 22 and a power conversion efficiency of 1.89%. This work demonstrates a good example for tuning absorption range, energy level, and photovoltaic properties of the polymers with different spacers and donor units can offer a simple and effective method to improve the efficiency of PSCs. (C) 2016 Wiley Periodicals, Inc.


Synthesis, characterizations and photovoltaic applications of dithienothiophene and benzotriazole containing conjugated polymers
Cevher, Şevki Can; Çırpan, Ali; Toppare, Levent Kamil; Department of Chemistry (2013)
Fused bithiophene containing conjugated polymers are recently used in different applications; for example organic light emitting diodes, solar cells, electrochromic devices and organic field effect transistors. Fused bithiophene derivatives increase the planarity, charge mobility and decrease band gap when incorporated into the polymer backbone. Connecting atom between the bithiopheneunit can be phosphorous, silicon, nitrogen and sulphur. In this thesis, dihienothiophene was coupled with benzotriazole via S...
Application of FAM ligands in the metal-promoted catalytic enantioselective synthesis of organic compounds
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Novel ferrocenyl substituted aziridinyl methanol (FAM) ligands were synthesized and successfully used in metal-promoted catalytic enantioselective azomethine ylide cycloadditions, diethylzinc additions to enones, alkynylzinc additions to aldehydes, diethylzinc additions to aldehydes, and Henry reactions. These reactions are summarized in this report.
The effect of the different donor units on fluorescent conjugated polymers containing 2,1,3-benzooxadiazole as the acceptor unit
Goker, Seza; Hizalan, Gonul; Ileri, Merve; Hacioglu, Serife O.; Toppare, Levent Kamil (2015-08-15)
A series of monomers were synthesized via Stille coupling to obtain low-band gap conjugated polymers namely poly(5,6-bis(octyloxy)-4,7-di(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]oxadiazole (PTTBO)), poly(5,6-bis(octyloxy)-4,7-di(selenophen-2-yl)benzo[c][1,2,5]oxadiazole (PSBO)) and poly(5,6-bis(octyloxy)-4,7-di(furan-2-yl)benzo[c][1,2,5]oxadiazole (PFBO)) which comprise electron-rich thieno[3,2b]thiophene (TT), selenophene and furan, as the donor units in conjugation with electron-deficient 2,1,3-benzooxa...
Effect of Dithienopyrrole Unit on Electrochromic and Optical Properties of Benzotriazole-Based Conjugated Polymers
UNLU, Naime Akbasoglu; DENIZ, Tugba Kaya; SENDUR, Merve; Çırpan, Ali (2012-09-26)
A series of benzotriazole (BTz)- and dithienopyrrole (DTP)-based three polymers; poly[2-(2-dodecyl-2H-benzo[d][1,2,3]triazol-4-yl)-4-hexyl-4H-dithieno[3,2-b:2',3'-d]pyrrole] (P1), poly[2- (5-(2-dodecyl-7-(thiophen-2-yl)-2H-benzo[d][1,2,3]triazol-4-yl)thiophen-2-yl)-4-hexyl-4H-dithieno[3,2-b:2',3'-d]pyrrole] (P2), and poly[2-(5-(2-dodecyl-7-(4-hexylthiophen-2-yl)-2H-benzo[d][1,2,3]triazol-4-yl)-3-hexylthiophen-2-yl)-4-hexyl-4H-dithieno[3,2-b:2',3'-d]pyrrole] (P3) was synthesized via Stille coupling. To inves...
Use of purified and modified bentonites in linear low-density polyethylene/organoclay/compatibilizer nanocomposites
Seyidoglu, Tijen; Yılmazer, Ülkü (2012-05-05)
Polyethylene-based ternary nanocomposites were prepared with different clay structures, obtained by the modification of purified Resadiye bentonite as the reinforcement, a random terpolymer of ethylene, butyl acrylate, and maleic anhydride with the trade name Lotader3210 as the compatibilizer, and linear low-density polyethylene (LLDPE) as the polymer matrix in an intensive batch mixer. The quaternary ammonium/phosphonium salts used for the modification of bentonite were dimethyldioctadecyl ammonium (DMDA) ...
Citation Formats
S. Goker, G. HIZALAN, S. KUTKAN, Y. A. Udum, A. Çırpan, and L. K. Toppare, “Incorporation of Different Conjugated Linkers into Low Band Gap Polymers Based on 5,6-Bis(octyloxy)-2,1,3 benzooxadiazole for Tuning Optoelectronic Properties,” JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, pp. 2459–2467, 2016, Accessed: 00, 2020. [Online]. Available: