Syntheses, electrochemical and spectroelectrochemical characterization of benzothiadiazole and benzoselenadiazole based random copolymers

2016-6-13
Kutkan, Seda
Goker, Seza
Hacioglu, Serife O.
Toppare, Levent Kamil
Three novel donor-acceptor-donor type random copolymers based on benzothiadiazole (BTh) and benzoselenadiazole (BSe) were synthesized via Pd (0) catalyzed Suzuki polycondensation reaction. The two acceptor units were coupled with electron rich moieties which are carbazole (CZ), fluorene (FL) and silafluorene (SiFL). Monomers were characterized using H-1 and C-13-NMR spectroscopy. The number and weight average molecular weights of the polymers were calculated using gel permeation chromatography (GPC). All three polymers were electrochemically and spectroelectrochemically characterized. PBThBSeCZ, PBThBSeFL and PBThBSeSiFL showed only p-dopable character and their doping/dedoping potentials were determined as 1.4V/1.2V, 1.53V/1.27V and 1.8V/1.3V, respectively. Corresponding HOMO energy levels were calculated as -5.85eV, -6.05eV and -6.15eV whereas LUMO energy levels were found to be -3.67eV, -3.84eV and -3.77eV, respectively. PBThBSeCZ had lower HOMO level and band gap than PBThBSeFL and PBThBSeSiFL due to its increased electron donating capability of nitrogen atom in carbazole unit.
Journal of Macromolecular Science, Part A

Suggestions

Synthesis and electro-optical properties of new conjugated hybrid polymers based on furan and fluorene units
Gunes, Arzu; CİHANER, ATİLLA; Önal, Ahmet Muhtar (2013-02-01)
A novel series of hybrid monomers containing furan and fluorene units, namely 2-(2-(furan-2-yl)-9H-fluoren-7-yl)furan (FFF), 2,7-di(furan-2-yl)-9H-fluoren-9-one (FOF) and 2-(2-(furan-2-yl)-9,9-dihexyl-9H-fluoren-7-yl)furan (FHF), was synthesized and their electrochemical polymerization was achieved via potential cycling. Optical and electrochemical properties of the polymers, poly(2-(2-(furan-2-yl)9H-fluoren-7-yl)furan (PFFF), poly(2,7-di(furan-2-yl)-9H-fluoren-9-one) (PFOF) and poly(2-(2-(furan2-yl)-9,9-di...
Synthesis and electrochromic properties of trans-stilbene bearing copolymers obtained with different repeat unit and chain length
Karakus, Melike; Nurioglu, Ayda Goycek; Akpinar, Hava Zekiye; Toppare, Levent Kamil; Çırpan, Ali (Elsevier BV, 2013-6)
Three new random copolymers containing benzotriazole (BTz), thiophene (Th) and trans-stilbene (St) were synthesized via Stille coupling technique with different monomer ratios. In order to determine the effect of stilbene quantity on electrochromic properties of the polymers, feed ratios of the monomers were altered in chemical polymerization. Polymer chain length effect was also investigated via using different reaction times and the same feed ratio. The characteristics of the synthesized copolymers were c...
Syntheses of electroactive layers based on functionalized anthracene for electrochromic applications
Yıldırım, Ahmet; Tarkuc, S.; AK, MESUT; Toppare, Levent Kamil (Elsevier BV, 2008-05-30)
A new monomer (DTAT) was synthesized via linking 3,4-ethylenedioxythiophene (EDOT) on anthracene. The polymer, P(DTAT) was electrosynthesized by anodic oxidation of the corresponding monomer in 0.1 M LiClO4 acetonitrile (ACN) solution. The optical properties, the absorption spectra and the kinetics, were examined. Spectroelectrochemical analysis showed that P(DTAT) has an electronic band gap (due to pi-pi* transition) of 1.57 eV at 776 nm.
Syntheses and characterization of benzotriazole, thienopyrroledione and benzodithiophene containing conjugated random terpolymers for organic solar cells
Göksu, Kardelen.; Çırpan, Ali; Department of Chemistry (2019)
Two random terpolymers, PBTS and PBTSe were designed and synthesized successfully as the donor units for polymer organic solar cell. Desired terpolymers contain alkoxy-benzodithiophene as an electron rich unit and Noctylthieno[3,4,c]pyrrole-4,6-dione (TPD) as the electron deficient group. Furthermore, thiophene and selenophene π bridges were introduced to benzotriazole unit as the acceptor moieties into copolymer backbone. The properties of synthesized terpolymers solar cell device were investigated by opti...
Synthesis and electrochemical polymerization of D-A-D type monomers with thieno [3,4-c] pyrrole-4,6-dione acceptor unit
Çakal, Deniz; Cihaner, Atilla; Önal, Ahmet Muhtar (Elsevier BV, 2018-11-01)
In this study, three new donor-acceptor-donor type monomers bearing 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno [3,4-c]pyrrole- 4,6(5H)-dione (A) as an acceptor unit and thiophene, 3,4-ethylenedioxythiophene (EDOT) and 3,3-didecy1-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (didecyl-ProDOT) as donor units were synthesized via Stille cross-coupling reaction and their electrochemical polymerization by repetitive cycling was reported. The electrochemical and optical properties of the monomers ((5-(2-ethyl-liexyl)-1,...
Citation Formats
S. Kutkan, S. Goker, S. O. Hacioglu, and L. K. Toppare, “Syntheses, electrochemical and spectroelectrochemical characterization of benzothiadiazole and benzoselenadiazole based random copolymers,” Journal of Macromolecular Science, Part A, pp. 475–483, 2016, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/28429.