Synthesis and electropolymerization of thieno[3,4-c]pyrrole-4,6-dione based donor-acceptor-donor type monomers (original) (raw)
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Journal of Polymer Science Part A: Polymer Chemistry, 2012
A new benzo[1,2-b:4,5-b']dithiophene (BDT) building block with 4,8-disubstitution using 2-(2-ethylhexyl)-3-hexylthieno[3,2-b]thiophene as the substituent has been designed and synthesized. The new building block has been copolymerized with benzothiadiazole (BT) and 5,6-difluorobenzothiadiazole (fBT) by Suzuki and Stille coupling polymerization to synthesize donor-acceptor conjugated polymers. The optical and electrochemical properties of the synthesized copolymers were studied. Bulk heterojunction solar cells were fabricated using the donor-acceptor copolymers in conjunction with PC 71 BM and exhibited up to 4.20% power conversion efficiency. † Electronic supplementary information (ESI) available. See
European Polymer Journal, 2016
Four new donor-acceptor conjugated copolymers, containing pyrene moieties flanked by thienyl or bithienyl groups as a donor units and thieno[3,4-c]pyrrole-4,6-dione (TPD) as acceptor units, were successfully prepared via a direct arylation polymerisation method. While all polymers prepared had 2-ethylhexyloxy-substituents on the pyrene repeat units, two different alkylsusbtituents (octyl or 4-hexylphenyl groups) were attached to their TPD moieties. The influence of these different substituents as well as the number of thienyl units linking the pyrene and TPD units along polymer chains on the photophysical, electronic and photovoltaic properties of these materials was investigated. All polymers displayed good thermal stability up to 315°C. The optical band gap of the four polymers, PP EH DT-TPD O , PP EH DT-TPD HP , PP EH DT2-TPD O and PP EH DT2-TPD HP , were estimated to be 2.00, 2.06, 1.94 and 1.91 eV, respectively. Polymers that possessed a single thiophene unit attached to the pyrene unit, PP EH DT-TPD O and PP EH DT-TPD HP , displayed deeper HOMO levels compared to those with bithiophene units, PP EH DT2-TPD O a n d P P EH DT2-TPD HP. Photovoltaic devices were fabricated from all polymers. PP EH DT2-TPD O boasted the highest efficiency with a PCE (2.06 %), a FF of 53.07 %, a J sc of 4.66 mA/cm 2 and a V oc of 0.83 V.
Electrochimica Acta, 2000
The electrochemical behavior of 2,5-di-(-2-thienyl)-pyrrole (SNS) on Pt has been studied from a 10 mM monomer solution in 0.2 M LiClO 4 +ethanol or in 0.2 M LiCl +ethanol by cyclic voltammetry, chronopotentiometry and chronoamperometry. The monomer exhibits two similar consecutive oxidation processes. Uniform, adherent and electroactive films of dark-blue poly(SNS) doped with ClO 4 − or with Cl − are obtained at low potentials related to the first process. Reproducible film weights are found at 0.700 V versus AgAgCl during 360 s. The increase in transport rate of reactants by stirring the solution with a magnetic bar at 150 rpm accelerates the SNS electropolymerization, allowing to collect much more polymer weight than from the quiescent solution. The productivity of poly(SNS) doped with Cl − determined by 'ex situ' ultramicrogravimetry increases notably under stirring, although its percentage in Cl − is similar to that found under quiescent conditions. This is ascribed to the production of a major proportion of longer linear molecules in polymer, consistent with its higher conductivity when it is synthesized under stirring. This effect is not so clear for the poly(SNS) doped with ClO 4 − due to the little influence of stirring upon its productivity and conductivity. The detection of short linear oligomers in the soluble fractions of polymers in thioglycerol by mass spectrometry-fast atom bombardment allows to propose a radical polycondensation as initial electropolymerization mechanism.
Science and Technology Development Journal, 2016
A new monomer of N-benzoyl dithieno[2,3-b:2’,3’-d]pyrrole (BDP), has been successfully prepared via copper-catalyzed amidation. Then, this monomer was brominated to form 2,6-dibromo-n-benzoyl dithieno[2,3-b:2’,3’-d]pyrrole (DiBDP) monomer. The structures of monomers were confirmed via the nuclear magnetic resonance (1HNMR) and Fourier transform infrared (FT-IR). BDP and DiBDP monomers will be used as monomers for Suzuki polycondensation reaction to synthesize the donor-acceptor (D-A) conjugated polymers.