Skip to main content
SpringerLink
Log in

RETRACTED ARTICLE: Core–shell super-structures via smart deposition of naphthothiadiazole and benzodithiophene-possessing polymer backbones onto carbon nanotubes and photovoltaic applications thereof

  • Published:
Journal of Materials Science: Materials in Electronics Aims and scope Submit manuscript

This article was retracted on 10 October 2022

This article has been updated

Abstract

Core–shell super-structures were developed via π-stacking of poly[benzodithiophene-bis(decyltetradecyl-thien) naphthothiadiazole] (PBDT-DTNT) and poly[bis(triiso-propylsilylethynyl) benzodithiophene-bis(decyltetradecyl-thien) naphthobisthiadiazole] (PBDT-TIPS-DTNT-DT) as conductive shells onto carbon nanotubes (CNTs). Structure of conjugated polymers substantially determines their deposition model onto CNTs. Regioregular poly(3-hexyl thiophene) (P3HT) chains with hexyl side chains developed delicate nanofibrils with a base attached to CNT surface. However, PBDT-DTNT and PBDT-TIPS-DTNT-DT complicated conductive polymers with fused and infused thiophenic and benzenic rings preferred to be π-stacked with a face-on manner onto CNT surface and fabricate shells. Grafting of CNT surface with a polythiophene such as poly(3-dodecyl thiophene) (PDDT) introduced some defects onto the shell structure; because PBDT-DTNT and PBDT-TIPS-DTNT-DT polymers were not able to be π-deposited onto CNT surface grafted with PDDT. The PDDT grafts were considered as hindrances against the stacking of complicated polymers. The thickness of PBDT-DTNT and PBDT-TIPS-DTNT-DT shells ranged in 10–12 and 5–8 nm, respectively. Higher hindrance of TIPS side structures in PBDT-TIPS-DTNT-DT chains reflected thinner shells. By developing core–shells based on PBDT-TIPS-DTNT-DT and PBDT-DTNT, the conductivity reached 10.11 and 12.15 S/cm, respectively. Donor–acceptor core–shell nano-hybrids were then applied in active layer of photovoltaics. Efficiencies for CNT (core)-PBDT-DTNT (shell) and CNT (core)-PBDT-TIPS-DTNT-DT (shell) were 4.07 and 2.34%, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

Change history

References

  1. K. Khan, A. Kausar, A.U. Rahman, Modern drifts in conjugated polymers and nanocomposites for organic solar cells: a review. Polym. Plast. Technol. Eng. 54(2), 140–154 (2015)

    Article  CAS  Google Scholar 

  2. S. Bhadra, D. Khastgir, Degradation and stability of polyaniline on exposure to electron beam irradiation (structure–property relationship). Polym. Degrad. Stab. 92(10), 1824–1832 (2007)

    Article  CAS  Google Scholar 

  3. G. Li, R. Zhu, Y. Yang, Polymer solar cells. Nat. Photonics 6(3), 153–161 (2012)

    Article  CAS  Google Scholar 

  4. D. Dang, P. Zhou, L. Duan, X. Bao, R. Yang, W. Zhu, An efficient method to achieve a balanced open circuit voltage and short circuit current density in polymer solar cells. J. Mater. Chem. A 4(21), 8291–8297 (2016)

    Article  CAS  Google Scholar 

  5. Y. Li, Molecular design of photovoltaic materials for polymer solar cells: toward suitable electronic energy levels and broad absorption. Acc. Chem. Res. 45(5), 723–733 (2012)

    Article  CAS  Google Scholar 

  6. L. Huo, T. Liu, X. Sun, Y. Cai, A.J. Heeger, Y. Sun, Single-junction organic solar cells based on a novel wide-bandgap polymer with efficiency of 9.7%. Adv. Mater. 27(18), 2938–2944 (2015)

    Article  CAS  Google Scholar 

  7. G. Yu, J. Gao, J.C. Hummelen, F. Wudl, A.J. Heeger, Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science 270(5243), 1789–1791 (1995)

    Article  CAS  Google Scholar 

  8. L. Ye, S. Zhang, W. Zhao, H. Yao, J. Hou, Highly efficient 2D-conjugated benzodithiophene-based photovoltaic polymer with linear alkylthio side chain. Chem. Mater. 26(12), 3603–3605 (2014)

    Article  CAS  Google Scholar 

  9. N. Wang, W. Chen, W. Shen, L. Duan, M. Qiu, J. Wang, C. Yang, Z. Du, R. Yang, Novel donor–acceptor polymers containing o-fluoro-p-alkoxyphenyl-substituted benzo [1, 2-b: 4, 5-b′] dithiophene units for polymer solar cells with power conversion efficiency exceeding 9%. J. Mater. Chem. A 4(26), 10212–10222 (2016)

    Article  CAS  Google Scholar 

  10. Y. Liu, J. Zhao, Z. Li, C. Mu, W. Ma, H. Hu, K. Jiang, H. Lin, H. Ade, H. Yan, Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells. Nat. Commun. 5, 5293 (2014)

    Article  CAS  Google Scholar 

  11. Z. He, C. Zhong, S. Su, M. Xu, H. Wu, Y. Cao, Enhanced power-conversion efficiency in polymer solar cells using an inverted device structure. Nat. Photon. 6(9), 591–595 (2012)

    Article  Google Scholar 

  12. M. Wang, X. Hu, P. Liu, W. Li, X. Gong, F. Huang, Y. Cao, Donor–acceptor conjugated polymer based on naphtho [1, 2-c: 5, 6-c] bis [1, 2, 5] thiadiazole for high-performance polymer solar cells. J. Am. Chem. Soc. 133(25), 9638–9641 (2011)

    Article  CAS  Google Scholar 

  13. I. Osaka, T. Abe, M. Shimawaki, T. Koganezawa, K. Takimiya, Naphthodithiophene-based donor–acceptor polymers: versatile semiconductors for OFETs and OPVs. ACS Macro Lett. 1(4), 437–440 (2012)

    Article  CAS  Google Scholar 

  14. I. Osaka, M. Shimawaki, H. Mori, I. Doi, E. Miyazaki, T. Koganezawa, K. Takimiya, Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer. J. Am. Chem. Soc. 134(7), 3498–3507 (2012)

    Article  CAS  Google Scholar 

  15. P. Guo, Y. Xia, F. Huang, G. Luo, J. Li, P. Zhang, Y. Zhu, C. Yang, H. Wu, Y. Cao, An alkylthieno-2-yl flanked dithieno [2, 3-d: 2′, 3′-d′] benzo [1, 2-b: 4, 5-b′] dithiophene-based low band gap conjugated polymer for high performance photovoltaic solar cells. RSC Adv. 5(17), 12879–12885 (2015)

    Article  CAS  Google Scholar 

  16. E. Bundgaard, F.C. Krebs, Low-band-gap conjugated polymers based on thiophene, benzothiadiazole, and benzobis (thiadiazole). Macromolecules 39(8), 2823–2831 (2006)

    Article  CAS  Google Scholar 

  17. T.T. Steckler, X. Zhang, J. Hwang, R. Honeyager, S. Ohira, X.H. Zhang, A. Grant, S. Ellinger, S.A. Odom, D. Sweat, D.B. Tanner, A spray-processable, low bandgap, and ambipolar donor–acceptor conjugated polymer. J. Am. Chem. Soc. 131(8), 2824–2826 (2009)

    Article  CAS  Google Scholar 

  18. J. Tong, L. An, J. Li, P. Zhang, P. Guo, C. Yang, Q. Su, X. Wang, Y. Xia, Large branched alkylthienyl bridged naphtho [1,2-c:5,6-c′] bis [1,2,5] thiadiazole-containing low bandgap copolymers: Synthesis and photovoltaic application. J. Macromol. Sci. Part A 54(3), 176–185 (2017)

    Article  CAS  Google Scholar 

  19. I. Osaka, T. Kakara, N. Takemura, T. Koganezawa, K. Takimiya, Naphthodithiophene–naphthobisthiadiazole copolymers for solar cells: alkylation drives the polymer backbone flat and promotes efficiency. J. Am. Chem. Soc. 135(24), 8834–8837 (2013)

    Article  CAS  Google Scholar 

  20. X. Hu, M. Wang, F. Huang, X. Gong, Y. Cao, 23% Enhanced efficiency of polymer solar cells processed with 1-chloronaphthalene as the solvent additive. Synth. Met. 164, 1–5 (2013)

    Article  CAS  Google Scholar 

  21. Y. Sun, J. Seifter, M. Wang, L.A. Perez, C. Luo, G.C. Bazan, F. Huang, Y. Cao, A.J. Heeger, Effect of molecular order on the performance of naphthobisthiadiazole-based polymer solar cells. Adv. Energy Mater. 4(6), 1–5 (2014)

    Article  CAS  Google Scholar 

  22. C. Mu, P. Liu, W. Ma, K. Jiang, J. Zhao, K. Zhang, Z. Chen, Z. Wei, Y. Yi, J. Wang, S. Yang, High-efficiency all-polymer solar cells based on a pair of crystalline low-bandgap polymers. Adv. Mater. 26(42), 7224–7230 (2014)

    Article  CAS  Google Scholar 

  23. V. Vohra, K. Kawashima, T. Kakara, T. Koganezawa, I. Osaka, K. Takimiya, H. Murata, Nat. Photon. 9, 403–409 (2015)

    Article  CAS  Google Scholar 

  24. L. Huo, Y. Zhou, Y. Li, Alkylthio-substituted polythiophene: absorption and photovoltaic properties. Macromol. Rapid Commun. 30(11), 925–931 (2009)

    Article  CAS  Google Scholar 

  25. C. Cui, W.Y. Wong, Y. Li, Improvement of open-circuit voltage and photovoltaic properties of 2D-conjugated polymers by alkylthio substitution. Energy Environ. Sci. 7(7), 2276–2284 (2014)

    Article  CAS  Google Scholar 

  26. J.H. Kim, M. Lee, H. Yang, D.H. Hwang, A high molecular weight triisopropylsilylethynyl (TIPS)-benzodithiophene and diketopyrrolopyrrole-based copolymer for high performance organic photovoltaic cells. J. Mater. Chem. A 2(18), 6348–6352 (2014)

    Article  CAS  Google Scholar 

  27. S. Wood, J.H. Kim, D.H. Hwang, J.S. Kim, Effects of fluorination and side chain branching on molecular conformation and photovoltaic performance of donor–acceptor copolymers. Chem. Mater. 27(12), 4196–4204 (2015)

    Article  CAS  Google Scholar 

  28. H. Gu, T.M. Swager, Fabrication of free-standing, conductive, and transparent carbon nanotube films. Adv. Mater. 20(23), 4433–4437 (2008)

    Article  CAS  Google Scholar 

  29. R. Allen, L. Pan, G.G. Fuller, Z. Bao, Using in-situ polymerization of conductive polymers to enhance the electrical properties of solution-processed carbon nanotube films and fibers. ACS Appl. Mater. Interfaces 6(13), 9966–9974 (2014)

    Article  CAS  Google Scholar 

  30. X.I.A.O.L.E.I. Liu, J. Ly, S.O.N.G. Han, D.A.I.H.U.A. Zhang, A. Requicha, M.E. Thompson, C.H.O.N.G.W.U. Zhou, Synthesis and electronic properties of individual single-walled carbon nanotube/polypyrrole composite nanocables. Adv. Mater. 17(22), 2727–2732 (2005)

    Article  CAS  Google Scholar 

  31. I.A. Tchmutin, A.T. Ponomarenko, E.P. Krinichnaya, G.I. Kozub, O.N. Efimov, Electrical properties of composites based on conjugated polymers and conductive fillers. Carbon 41(7), 1391–1395 (2003)

    Article  CAS  Google Scholar 

  32. R.G. Goh, N. Motta, J.M. Bell, E.R. Waclawik, Effects of substrate curvature on the adsorption of poly (3-hexylthiophene) on single-walled carbon nanotubes. Appl. Phys. Lett. 88(5), 053101 (2006)

    Article  Google Scholar 

  33. A. Star, J.F. Stoddart, D. Steuerman, M. Diehl, A. Boukai, E.W. Wong, X. Yang, S.W. Chung, H. Choi, J.R. Heath, Preparation and properties of polymer-wrapped single-walled carbon nanotubes. Angew. Chem. Int. Ed. 40(9), 1721–1725 (2001)

    Article  CAS  Google Scholar 

  34. J. Chen, H. Liu, W.A. Weimer, M.D. Halls, D.H. Waldeck, G.C. Walker, Noncovalent engineering of carbon nanotube surfaces by rigid, functional conjugated polymers. J. Am. Chem. Soc. 124(31), 9034–9035 (2002)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemical Engineering Department, Faculty of Engineering, Azarbaijan Shahid Madani University, P.O. Box: 5375171379, Tabriz, Iran

    Samira Agbolaghi

Authors
  1. Samira Agbolaghi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Samira Agbolaghi.

Additional information

This article has been retracted. Please see the retraction notice for more detail:https://doi.org/10.1007/s10854-022-09186-6

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 155 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Agbolaghi, S. RETRACTED ARTICLE: Core–shell super-structures via smart deposition of naphthothiadiazole and benzodithiophene-possessing polymer backbones onto carbon nanotubes and photovoltaic applications thereof. J Mater Sci: Mater Electron 30, 832–841 (2019). https://doi.org/10.1007/s10854-018-0353-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10854-018-0353-x

Search

Navigation