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Photophysics and thermally-induced degradation of P2TI-DD, a polymer synthesized by direct arylation reaction

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Abstract

A low band gap (\(E_\text {g} = 1.6 ~ \text {eV}\)) copolymer, P2TI-DD, with bithiophene donor and 2-decyldodecyl (DD)-substituted isoindigo acceptor was successfully prepared using direct arylation polycondensation method. Its HOMO and LUMO energy levels were found to be \(-5.47\) and \(-3.79 ~ \text {eV}\), respectively. The PL spectra of P2TI-DD in solvents of different polarity were found to red-shift with increasing solvent polarity while its absorption remained the same, confirming the intramolecular charge transfer characteristics of its excited state and non-polar ground state, respectively. The deconvoluted PL spectra of the copolymer confirmed the presence of inter-chain exciton in the poor solvent, cyclohexane and thin films while it is missing in the chlorinated solvents. Thermally induced degradation reduced the absorption of P2TI-DD by 35% after heating at 85 °C   for more than 190 h. The main degradation mechanism in the copolymer was found to be chain scission as confirmed by the increase in the free exciton bandwidth and the appearance of a blue-shifted emission. The thermal decomposition temperature of P2TI-D was around 330 °C. Its X-ray diffraction traces revealed a sharp peak which corresponds to ordered lamellar (100) planes and a broad halo (010) due to the characteristics of π–π interchain stacking in the films.

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References

  1. B. Du, R. Geng, W. Tan, Y. Mao, D. Li, X. Zhang, D. Liu, W. Tang, W. Huang, T. Wang, Heating induced aggregation in non-fullerene organic solar cells towards high performance. J. Energy Chem. 54, 131–137 (2021)

    Article  Google Scholar 

  2. Q. Liu, Y. Jiang, K. Jin, J. Qin, X. Jingui, W. Li, J. Xiong, J. Liu, Z. Xiao, K. Sun et al., 18% efficiency organic solar cells. Sci. Bull. 65(4), 272–275 (2020)

    Article  CAS  Google Scholar 

  3. Y. Cui, H. Yao, J. Zhang, K. Xian, T. Zhang, L. Hong, Y. Wang, X. Ye, K. Ma, C. An et al., Single-junction organic photovoltaic cells with approaching 18% efficiency. Adv. Mater. 32(19), 1908205 (2020)

    Article  CAS  Google Scholar 

  4. J. Xiong, K. Jin, Y. Jiang, J. Qin, T. Wang, J. Liu, Q. Liu, H. Peng, X. Li, A. Sun et al., Thiolactone copolymer donor gifts organic solar cells a 16.72% efficiency. Sci. Bull. 64(21), 1573–1576 (2019)

    Article  CAS  Google Scholar 

  5. Y.-J. Cheng, S.-H. Yang, C.-S. Hsu, Synthesis of conjugated polymers for organic solar cell applications. Chem. Rev. 109(11), 5868–5923 (2009)

    Article  CAS  Google Scholar 

  6. A.V. Patil, W.-H. Lee, E. Lee, K. Kim, I.-N. Kang, S.-H. Lee, Synthesis and photovoltaic properties of a low-band-gap copolymer of dithieno [3, 2-b: 2’, 3’-d] thiophene and dithienylquinoxaline. Macromolecules 44(6), 1238–1241 (2011)

    Article  CAS  Google Scholar 

  7. J.D. Yuen, F. Wudl, Strong acceptors in donor-acceptor polymers for high performance thin film transistors. Energy Environ. Sci. 6(2), 392–406 (2013)

    Article  CAS  Google Scholar 

  8. J.E. Hyuk, A. Hyungju, J.W. Ho, J.J. Woong, J.J. Woong, Isoindigo-based conjugated polymer for high-performance organic solar cell with a high VOC of 1.06 V as processed from non-halogenated solvent. Dyes Pigment. 161, 113–118 (2019)

    Article  Google Scholar 

  9. L. Song-Fu, C. Chin-Ti, C. Chi-Yang, Isoindigo-dicyanobithiophene-based copolymer for high performance polymer-fullerene solar cells reaching 1.06 V open circuit voltage and 8.36% power conversion efficiency. ACS Macro Lett. 6(9), 969–974 (2017)

    Article  Google Scholar 

  10. C.H. Yeon, P. Jung-Hwa, C. Junjie, K. Su-Yeon, O. Juwon, K. Dongho, P.S. Young, Influence of intramolecular charge-transfer characteristics of excitons on polaron generation at the donor/acceptor interface in polymer solar cells. J. Phys. Chem. C 125(33), 18352–18361 (2021)

    Article  Google Scholar 

  11. T. Keller, T. Gahlmann, T. Riedl, U. Scherf, Direct arylation polycondensation (dap) synthesis of alternating quaterthiophene–benzothiadiazole copolymers for organic solar cell applications. ChemPlusChem 84(9), 1249–1252 (2019)

    Article  CAS  Google Scholar 

  12. C. Dan, Q. Shengchun, W. Zhanguo, W. Jizheng, High efficiency P3HT:PCBM solar cells with an inserted PCBM layer. J. Mater. Chem. C 2(22), 4383–4387 (2014)

    Article  Google Scholar 

  13. N.A. Tegegne, Z. Abdissa, W. Mammo, M.R. Andersson, D. Schlettwein, H. Schwoerer, Ultrafast excited state dynamics of a bithiophene–isoindigo copolymer obtained by direct arylation polycondensation and its application in indium tin oxide-free solar cells. J. Polym. Sci., Part B: Polym. Phys. 56(21), 1475–1483 (2018)

    Article  CAS  Google Scholar 

  14. ASTM International, Standard Test Methods for Photovoltaic Modules in Cyclic Temperature and Humidity Environments ASTM e1171–15 (ASTM International, West Conshohocken, 2015)

    Google Scholar 

  15. M. Zhiying, G. Hua, W. Dong, S. Zhigang, Influence of alkyl side-chain length on the carrier mobility in organic semiconductors: herringbone vs. pi-pi stacking. J. Mater. Chem. C 4(20), 4546–4555 (2016)

    Article  Google Scholar 

  16. F.C. Spano, C. Silva, H-and J-aggregate behavior in polymeric semiconductors. Annu. Rev. Phys. Chem. 65, 477–500 (2014)

    Article  CAS  Google Scholar 

  17. Y. Yan, Y. Bohao, Y. Yongjie, Z. Hailiang, Novel side-chain alternative copolymer combined FRET and DRET with large pseudo-Stokes shift and polarity-sensitive fluorescence behavior. J. Mater. Chem. C 7(36), 11285–11292 (2019)

    Article  Google Scholar 

  18. A. Tegegne Newayemedhin, A. Zelalem, M. Wendimagegn, U. Takayuki, O.-S. Yoshiko, G. Francesco, P. William, R. Andersson Mats, S. Derck, V. Varun et al., Effect of alkyl side chain length on intra-and intermolecular interactions of terthiophene–isoindigo copolymers. J. Phys. Chem. C 124(18), 9644–9655 (2020)

    Article  Google Scholar 

  19. Z.E. Lampert, C.L. Reynolds Jr., J.M. Papanikolas, M. Osama Aboelfotoh, Controlling morphology and chain aggregation in semiconducting conjugated polymers: the role of solvent on optical gain in meh-ppv. J. Phys. Chem. B 116(42), 12835–12841 (2012)

    Article  CAS  Google Scholar 

  20. N.A. Tegegne, Z. Abdissa, W. Mammo, Photophysical, thermal and structural properties of thiophene and benzodithiophene-based copolymers synthesized by direct arylation polycondensation method. Polymers 13(7), 1151 (2021)

    Article  CAS  Google Scholar 

  21. M.G. Tessema, A. Newayemedhin, Correlation between LUMO offset of donor/acceptor molecules to an open circuit voltage in bulk heterojunction solar cell. Phys B Condens. Matter 445, 56–59 (2014)

    Article  Google Scholar 

  22. Z. Ma, E. Wang, M.E. Jarvid, P. Henriksson, O. Inganäs, F. Zhang, M.R. Andersson, Synthesis and characterization of benzodithiophene–isoindigo polymers for solar cells. J. Mater. Chem. 22(5), 2306–2314 (2012)

    Article  CAS  Google Scholar 

  23. C. Jenny, S. Carlos, H. Friend Richard, C. Spano Frank, Role of intermolecular coupling in the photophysics of disordered organic semiconductors: aggregate emission in regioregular polythiophene. Phys. Rev. Lett. 98(20), 206406 (2007)

    Article  Google Scholar 

  24. C. Jenny, C. Jui-Fen, C. Spano Frank, H. Friend Richard, S. Carlos, Determining exciton bandwidth and film microstructure in polythiophene films using linear absorption spectroscopy. Appl. Phys. Lett. 94(16), 117 (2009)

    Google Scholar 

  25. N.A. Tegegne, Aggregation and thermally induced photo-physics and structural ordering of thiophene–quinoxaline copolymer. Mater. Res. Express 8(9), 095307 (2021)

    Article  CAS  Google Scholar 

  26. M.L. Raicoski, M.G. Vivas, Photobleaching kinetics of meh-ppv in solution: the role of conformational disorder. J. Phys. Chem. B 125(34), 9887–9894 (2021)

    Article  CAS  Google Scholar 

  27. M. Manceau, A. Rivaton, J.-L. Gardette, S. Guillerez, N. Lemaître, The mechanism of photo-and thermooxidation of poly (3-hexylthiophene)(p3ht) reconsidered. Polym. Degrad. Stab. 94(6), 898–907 (2009)

    Article  CAS  Google Scholar 

  28. H.F. Dam, T.R. Andersen, M.V. Madsen, T.K. Mortensen, M.F. Pedersen, U. Nielsen, F.C. Krebs, Roll and roll-to-roll process scaling through development of a compact flexo unit for printing of back electrodes. Solar Energy Mater. Solar Cells 140, 187–192 (2015)

    Article  CAS  Google Scholar 

  29. B.S. Desalegn, N. Bekri, F.G. Hone, D.M. Andoshe, W. Mammo, Z. Abdissa, G. Bosman, N.A. Tegegne, One-pot synthesis and thermal stability of thiophene-bridged thieno [3, 2-b] thiophene donor-based copolymers. Mater. Today Commun. 29, 102803 (2021)

    Article  CAS  Google Scholar 

  30. L. Fernandes, H. Gaspar, J.P.C. Tomé, F. Figueira, G. Bernardo, Thermal stability of low-bandgap copolymers ptb7 and ptb7-th and their bulk heterojunction composites. Polym. Bull. 75(2), 515–532 (2018)

    Article  CAS  Google Scholar 

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Funding

NB, ZA and WM would like to acknowledge the financial support from the International Science Program (ISP), Uppsala Univeristy, Sweden. NT would like to acknowledge the financial support from Organization for Women in Science for the Developing World (OWSD).

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Authors and Affiliations

  1. Department of Physics, Addis Ababa University, 1176, Addis Ababa, Ethiopia

    Nika Bekri, Eninges Asmare & Newayemedhin A. Tegegne

  2. Department of Physics and Statistics, Addis Ababa Science and Technology University, 16417, Addis Ababa, Ethiopia

    Nika Bekri

  3. Department of Chemistry, Addis Ababa University, 33658, Addis Ababa, Ethiopia

    Zelalem Abdissa & Wendimagegn Mammo

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  1. Nika Bekri
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  2. Eninges Asmare
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  5. Newayemedhin A. Tegegne
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Correspondence to Newayemedhin A. Tegegne.

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10854_2022_8499_MOESM1_ESM.docx

Details of materials used, molecular weight determination, and PL of P2TI-DD in solution and DFT results such as the optimized geometry and ESP of the mono-and di-mer are included. Supplementary file1 (DOCX 1179 kb)

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Bekri, N., Asmare, E., Abdissa, Z. et al. Photophysics and thermally-induced degradation of P2TI-DD, a polymer synthesized by direct arylation reaction. J Mater Sci: Mater Electron 33, 16066–16076 (2022). https://doi.org/10.1007/s10854-022-08499-w

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