Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications

Download
index.pdf
2021-12-01
Cevher, Duygu
Taşkaya Aslan, Sultan
Bolayır, Eda
Hizalan Ozsoy, Gonul
UDUM, YASEMİN
Yıldırım, Erol
Toppare, Levent Kamil
Çırpan, Ali
Show full item record
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
333
views
205
downloads
A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were performed on model tetramer structures to shed light on how substituting the fluorine atom to the acceptor building block affects the structural, electronic and optical properties of the polymers. The results of computational studies were compared with experimental studies. The structure adjustment accomplished by fluorine substitution on the benzothiadiazole moiety reveals an influence on the electronic structure of polymers with a more negative HOMO energy level. A high VOC for the resulting photovoltaic device was examined for PBDTSe-FFBT. Difluorinated polymer PBDTSe-FFBT:PC71BM organic solar cell exhibited the highest photovoltaic performance of 2.63% with JSC of 7.24 mA cm-2, VOC of 0.72 V and FF of 50.6%. PBDTSe-BT:PC71BM revealed the best PCE as 2.39%, and the device reached the highest efficiency up to 1.68% for PBDTSe-FBT:PC71BM.
Benzodithiophene, Benzothiadiazole, Fluorine substitution, Power conversion efficiency, Organic solar cell
https://hdl.handle.net/11511/93767
Electrochimica Acta
Department of Chemistry, Article

Suggestions

Synthesis, characterization and photovoltaic properties of benzo[c][1,2,5]oxadiazole based conjugated polymers for organic solar cells
Karakurt, Oğuzhan; Çırpan, Ali; Günbaş, Emrullah Görkem; Department of Chemistry (2021-1-22)
In this thesis, six conjugated polymers were synthesized by coupling of 2,1,3- benzoxadiazole derivatives with donor groups via Stille polycondensation reactions. Moreover, the effect of molecular weight for P1 and P2, effect of position of alkyl chain for P5 and effect of π-bridge groups for P6 which are selenophene and thiophene on optical, electrochemical, and photovoltaic properties were investigated. Also, modifications on alkyl chains of P3 and P4 were performed to increase their functionalities via p...
Investigation the effect of π bridge and side chain on photovoltaic properties of benzodithiophene and quinoxaline based conjugated polymers
Taşkaya Aslan, Sultan; Alemdar, Eda; Hacıefendioğlu, Tuğba; UDUM, YASEMİN; Toppare, Levent Kamil; Yıldırım, Erol; Çırpan, Ali (2022-04-15)
© 2022 Elsevier LtdA series of donor–acceptor type alternative polymers containing 2D-BDT and 1D-BDT as the donors and quinoxaline as the acceptor were successfully obtained by Stille coupling reactions. Synthesized polymers containing selenophene and thiophene as π-bridges in their backbones and 2-ethylhexylselenophene and 2-ethylhexylalkoxy side groups on the BDT structure were named as P1, P2, P3 and P4, respectively. Eonsetox and Eonsetred were investigated for P1, P2, P3, and P4, respectively. Onset ox...
Syntheses of conjugated polymers and investigation the effect of gold nanoparticle - thiol interaction for organic solar cell application
Gülmez, Selin; Çırpan, Ali; Department of Chemistry (2022-8-31)
In this thesis, five benzo[c][1,2,5] thiadiazole-based conjugated polymers were synthesized. Four of them were synthesized via Stille and Suzuki coupling reactions and the remaining one was synthesized by post-polymerization. The effect of functional groups of the tip of the alkyl chain was analyzed. Moreover, thiol group and gold nanoparticle interaction on the organic solar cell efficiency for P1-SH were investigated. Electronic and optical band gaps of polymers were found as 1.85/1.81, 1.95/1.85, 1.83/1....
Synthesis of various camphor-based chiral pyridine derivatives
Işık, Murat; Tanyeli, Cihangir; Department of Chemistry (2005)
Chiral aromatic nitrogen heterocycles are finding many applications in asymmetric organic synthesis, particularly as ligands in the preparation of chiral metal complexes. Since camphor-based chiral auxiliaries are known to be especially effective, a number of pyridines fused to the camphor skeleton have been reported. It is well known that nicotinic acid and its derivatives exhibiting qualitatively the biological activity of nicotinamide, which acts as an electron acceptor in many biological redox reactions...
Synthesis of bistriphenylamine- and benzodithiophene-based random conjugated polymers for organic photovoltaic applications
CETIN, Asli; ISTANBULLUOGLU, Cagla; HACIOGLU, Serife Ozdemir; CEVHER, ŞEVKİ CAN; Toppare, Levent Kamil; Çırpan, Ali (2017-11-15)
In this study, donor-acceptor random polymers containing benzotriazole acceptor and bistriphenylamine and benzodithiophene donors, P1 and P2, were successfully synthesized by Stille coupling polymerization. The effect of bistriphenylamine moiety and thiophene -conjugated linker on electrochemical, spectroelectrochemical, and optical behaviors of the polymers were investigated. Optoelectronic properties and photovoltaic performance of the polymers were examined under the illumination of AM 1.5G, 100 mWcm(-2)...
Citation Formats
D. Cevher et al., “Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications,” Electrochimica Acta, vol. 398, pp. 0–0, 2021, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/93767.
METU IIS - Integrated Information Service open@metu.edu.tr