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Synthesis and characterization of n-type conjugated copolymers bearing perylene diimide moieties

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Abstract

Three electron-deficient conjugated polymers based on perylene diimide (PDI) units, namely, poly[(N,N′-didodecyl-3,4,9,10-perylene diimide-1,7-diyl)-alt-(9,9-dihexylfluorene-2,7-diyl)] (PPDIF), poly{(N,N′-didodecyl-3,4,9,10-perylene diimide-1,7-diyl)-alt-[N-(2-ethylhexyl) carbazole-3, 6-diyl]} (PPDIC) and poly{(N,N′-didodecyl-3,4,9,10-perylene diimide-1,7-diyl)-co-[N-(2-ethylhexyl) carbazole-3,6-diyl]-co-(9,9-dihexylfluorene-2,7-diyl)} (PPDICF) have been synthesized via Suzuki coupling reaction, and their chemical structures are confirmed by 1H NMR, 13C NMR and FT-IR. All these polymers show broad absorption bands in 250–700 nm, and their optical band gaps are calculated to be ~1.7 eV. Cyclic voltammetry results confirm that the objective macromolecules possess high electron affinity of ~3.9 eV. By employing poly-3-hexylthiophene (P3HT) as electron donor and PPDIC as electron acceptor, all polymer solar cells (aPSCs) with bulky heterojunction structure have been fabricated, preliminary results indicate they have one of the most highest open-circuit voltage (V oc) (0.86 V) reported so far in aPSCs with PDI-based polymers as electron acceptor.

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References

  1. Günes S, Neugebauer H, Sariciftci NS (2007) Conjugated polymer-based organic solar cells. Chem Rev 107:1324–1338

    Article  Google Scholar 

  2. Thompson BC, Fréchet JMJ (2008) Polymer-fullerene composite solar cells. Angew Chem Int Ed 47:58–77

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  4. Chen H, Hou J, Zhang S, Liang Y, Yang G, Yang Y, Yu L, Wu Y, Li G (2009) Polymer solar cells with enhanced open-circuit voltage and efficiency. Nat Photonics 3:649–653

    Article  CAS  Google Scholar 

  5. Hou J, Chen H, Zhang S, Chen RI, Yang Y, Wu Y, Li G (2009) Synthesis of a low band gap polymer and its application in highly efficient polymer solar cells. J Am Chem Soc 131:15586–15587

    Article  CAS  Google Scholar 

  6. Park SH, Roy A, Beaupré S, Cho S, Coates N, Moon JS, Moses D, Leclerc M, Lee K, Heeger AJ (2009) Bulk heterojunction solar cells with internal quantum efficiency approaching 100%. Nat Photonics 3:297–302

    Article  CAS  Google Scholar 

  7. Kim JY, Lee K, Coates NE, Moses D, Nguyen TQ, Dante M, Heeger AJ (2007) Efficient tandem polymer solar cells fabricated by all-solution processing. Science 317:222–225

    Article  CAS  Google Scholar 

  8. Zhan X, Tan Z, Domercq B, An Z, Zhang X, Barlow S, Li Y, Zhu D, Kippelen B, Marder SR (2007) A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells. J Am Chem Soc 129:7246–7247

    Article  CAS  Google Scholar 

  9. Tan Z, Zhou E, Zhan X, Wang X, Li Y, Barlow S, Marder SR (2008) Efficient all-polymer solar cells based on blend of tris(thienylenevinylene)-substituted polythiophene and poly[perylene diimide-alt-bis(dithienothiophene)]. Appl Phys Lett 93:73303–73309

    Article  Google Scholar 

  10. Zhou Y, Pei J, Dong Q, Sun X, Liu Y, Tian W (2009) Donor-acceptor molecule as the acceptor for polymer-based bulk heterojunction solar cells. J Phys Chem C 113:7882–7886

    Article  CAS  Google Scholar 

  11. Yu G, Heeger AJ (1995) Charge separation and photovoltaic conversion in polymer composites with internal donor/acceptor heterojunctions. J Appl Phys 78:4510–4515

    Article  CAS  Google Scholar 

  12. McNeill CR, Halls JJM, Wilson R, Whiting GL, Berkebile S, Ramsey MG, Friend RH, Greenham NC (2008) Efficient polythiophene/polyfluorene copolymer bulk heterojunction photovoltaic devices: device physics and annealing effects. Adv Funct Mater 18:2309–2321

    Article  CAS  Google Scholar 

  13. Mikroyannidis JA, Stylianakis MM, Sharma GD, Balraju P, Roy MS (2009) A novel alternating phenylenevinylene copolymer with perylene bisimide units: synthesis, photophysical, electrochemical, and photovoltaic properties. J Phys Chem C 113:7904–7912

    Article  CAS  Google Scholar 

  14. Sang G, Zhou E, Huang Y, Zou Y, Zhao G, Li Y (2009) Incorporation of thienylenevinylene and triphenylamine moieties into polythiophene side chains for all-polymer photovoltaic applications. J Phys Chem C 113:5879–5885

    Article  CAS  Google Scholar 

  15. McNeill CR, Abrusci A, Zaumseil J, Wilson R, McKiernan MJ, Burroughes JH, Halls JJM, Greenham NC, Friend RH (2007) Dual electron donor/electron acceptor character of a conjugated polymer in efficient photovoltaic diodes. Appl Phys Lett 90:193506

    Article  Google Scholar 

  16. Kozma E, Kotowski D, Bertini F, Luzzati S, Catellani M (2010) Synthesis of donor-acceptor poly (perylene diimide-altoligothiophene) copolymers as n-type materials for polymeric solar cells. Polymer 51:2264–2270

    Article  CAS  Google Scholar 

  17. Tan Z, Zhou E, Zhan X, Wang X, Li Y, Barlow S, Marder SR (2008) Efficient all-polymer solar cells based on blend of tris(thienylenevinylene)-substituted polythiophene and poly[perylene diimide-alt-bis(dithienothiophene)]. Appl Phys Lett 93:73309

    Article  Google Scholar 

  18. Zhan X, Tan Z, Zhou E, Li Y, Misra R, Grant A, Domercq B, Zhang X, An Z, Zhang X, Barlow S, Kippelen B, Marder SR (2009) Copolymers of perylene diimide with dithienothiophene and dithienopyrrole as electron-transport materials for all-polymer solar cells and field-effect transistors. J Mater Chem 19:5794–5803

    Article  CAS  Google Scholar 

  19. Zhou E, Tajima K, Yang CH, Hashimoto K (2010) Band gap and molecular energy level control of perylene diimide-based donor–acceptor copolymers for all-polymer solar cells. J Mater Chem 20:2362–2368

    Article  CAS  Google Scholar 

  20. Qin R, Li W, Li C, Du C, Veit C, Schleiermacher HF, Andersson M, Bo Z, Liu Z, Anginäs O, Wuerfel U, Zhang F (2009) A planar copolymer for high efficiency polymer solar cells. J Am Chem Soc 131:14612–14613

    Article  CAS  Google Scholar 

  21. Lai M-H, Tsai J-H, Chueh C-C, Wang C-F, Chen W-C (2010) Syntheses of new 3,6-carbazole-based donor/acceptor conjugated copolymers for optoelectronic device applications. Macromol Chem Phys 211:2017–2025

    Article  CAS  Google Scholar 

  22. Zhou E, Cong J, Yamakawa S, Wei Q, Nakamura M, Tajima K, Yang C, Hashimoto K (2010) Synthesis of thieno[3,4-b]pyrazine-based and 2,1,3-benzo-thiadiazole-based donor–acceptor copolymers and their application in photovoltaic devices. Macromolecules 43:2873–2879

    Article  CAS  Google Scholar 

  23. Zhou E, Cong J, Tajima K, Hashimoto K (2010) Synthesis and photovoltaic properties of donor–acceptor copolymers based on 5,8-dithien-2-yl-2,3-diphenylquinoxaline. Chem Mater 22:4890–4895

    Article  CAS  Google Scholar 

  24. Salim T, Sun S, Wong LH, Xi L, Foo YL, Lam YM (2010) The role of poly(3-hexylthiophene) nanofibers in an all-polymer blend with a polyfluorene copolymer for solar cell applications. J Phys Chem C 114:9459–9468

    Article  CAS  Google Scholar 

  25. Ranger M, Rondeau D, Leclerc M (1997) New well-defined poly (2,7-fluorene) derivatives: photoluminescence and base doping. Macromolecules 30:7686–7691

    Article  CAS  Google Scholar 

  26. Ahrens MJ, Sinks LE, Rybtchinski B, Liu W, Jones BA, Giaimo JM, Gusev AV, Goshe AJ, Tiede DM, Wasielewski MR (2004) Self-assembly of supramolecular light-harvesting arrays from covalent multi-chromophore perylene-3,4:9,10-bis(dicarboximide) building blocks. J Am Chem Soc 126:8284–8294

    Article  CAS  Google Scholar 

  27. Liu S-J, Zhao Q, Chen R-F, Deng Y, Fan Q-L, Li F-Y, Wang L-H, Huang C-H, Huang W (2006) π-Conjugated chelating polymers with charged iridium complexes in the backbones: synthesis, characterization, energy transfer, and electrochemical properties. Chem Eur J 12:4351–4361

    Article  CAS  Google Scholar 

  28. Li Y, Ding J, Day M, Tao Y, Lu J, D’iorio M (2004) Synthesis and properties of random and alternating fluorene/carbazole copolymers for use in blue light-emitting devices. Chem Mater 16:2165–2173

    Article  CAS  Google Scholar 

  29. Bettington S, Tavasli M, Bryce MR, Beeby A, Al-Attar H, Monkman AP (2007) Tris-cyclometalated iridium(III) complexes of carbazole(fluorenyl)pyridine ligands: synthesis, redox and photophysical properties, and electrophosphorescent light-emitting diodes. Chem Eur J 13:1423–1431

    Article  CAS  Google Scholar 

  30. Qi ZJ, Wei B, Sun YM, Wang XM, Kang F, Hong MX, Tang LL (2010) Comparative study of photoelectric properties of regiosymmetrical poly(3,4-dialkoxythiophene)s. Polym Bull. doi 10.1007/s00289-010-0324-8

  31. Liu MS, Luo J, Jen AK-Y (2003) Efficient green-light-emitting diodes from silole-containing copolymers. Chem Mater 15:3496–3500

    Article  CAS  Google Scholar 

  32. Wang Y, Yang L, Yao C, Qin W, Yin S, Zhang F (2011) Enhanced performance and stability in polymer photovoltaic cells using lithium benzoate as cathode interfacial layer. Sol Energy Mater Sol Cells 95:1243–1247

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This study was supported by the National Natural Science Foundation of China (Project grant No. 50803040 and 20872103) and the Open Project Program of Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, China (No. 10HJYH02). We are greatly thank to the analytical & testing center of Sichuan University for providing measurements of NMR, UV–Vis and PL data for the intermediates and objective compounds.

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Authors and Affiliations

  1. College of Chemistry, Sichuan University, Chengdu, 610064, China

    Er-Fu Huo, Yong Zou, Yan Huang, Zhi-Yun Lu & Qing Jiang

  2. Key Laboratory of Luminescence and Optical Information, Ministry of Education, Beijing Jiaotong University, Beijing, 100044, China

    Jing-Lu Bai & Su-Ling Zhao

  3. Analytical & Testing Center, Sichuan University, Chengdu, 610064, China

    Hui-Qin Sun

  4. Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Hunan, 411105, People’s Republic of China

    Yu Liu

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  1. Er-Fu Huo
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  2. Yong Zou
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Correspondence to Yan Huang or Su-Ling Zhao.

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Huo, EF., Zou, Y., Sun, HQ. et al. Synthesis and characterization of n-type conjugated copolymers bearing perylene diimide moieties. Polym. Bull. 67, 843–857 (2011). https://doi.org/10.1007/s00289-011-0471-6

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  • DOI: https://doi.org/10.1007/s00289-011-0471-6

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