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Synthesis and characterization of 5,6-bis(n-octyloxy)[2,1,3] selenadiazole-based polymers for photovoltaic applications

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Abstract

Two D–A conjugated polymers containing benzo[1,2-b:4,5-b’] dithiophene (BDT), benzo[1,2-b:4,5-b’]difuran (BDF) donor units and 4,7-di(thiophen-2-yl)-5,6-bis(n-octyloxy)[2,1,3]benzoselenadiazole (DTBSe) acceptor unit, namely PBDTDTBSe and PBDFDTBSe have been synthesized by Stille coupling polymerization. The two polymers show good solubility in common organic solvents, good film forming properties, broad absorption (350–700 nm), low optical band gap (about 1.60 eV) and relatively high hole mobility [1.22 × 10−2 cm−2/(V.s)]. The devices based on the blend film of PBDFDTBSe and PC71BM (1:1, w/w) exhibited the best device performance with PCE of 3.28 %, V oc of 0.71 V, J sc of 10.37 mA cm−2 and FF of 44.6 % under illumination of AM 1.5 G (100 mW cm−2).

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References

  1. Kim JY, Lee K, Coates NE, Moses D, Nguyen TQ, Dante M, Heeger A (2007) Science 317:222

    Article  CAS  Google Scholar 

  2. Liu YH, Zhao JB, Li ZhK, Mu Ch, Ma W, Hu HW, Jiang K, Lin HR, Ade H, Yan H (2014) Nat Commun. doi:10.1038/ncomms6293

    Google Scholar 

  3. You JB, Chen CC, Hong ZR, Yoshimura K, Ohya K, Xu R, Ye ShL, Gao J, Li G, Yang Y (2013) Adv Mater 25(29):3973

    Article  CAS  Google Scholar 

  4. Yang JL, Yan DH, Jones TS (2015) Chem Rev 115:5570

    Article  CAS  Google Scholar 

  5. Ye L, Zhang ShQ, Zhao WCh, Yao HF, Hou JH (2014) Chem Mater 26(12):3603

    Article  CAS  Google Scholar 

  6. You JB, Dou LT, Yoshimura K, Kato T, Ohya K, Moriarty T, Emery K, Chen CC, Gao J, Li G, Yang Y (2013) Nat Commun 4:1446

    Article  Google Scholar 

  7. Chen JW, Cao Y (2009) Acc Chem Res 11:1709

    Article  Google Scholar 

  8. Zhan XW, Zhu DB (2010) Polym Chem 1:409

    Article  CAS  Google Scholar 

  9. Huo LJ, Huang Y, Fan BH, Guo X, Jing Y, Zhang MJ, Li YF, Hou JH (2012) Chem Commun 48:3318

    Article  CAS  Google Scholar 

  10. Yang M, Peng B, Liu B, Zou YP, Zhou KC, He YH, Pan CY, Li YF (2010) J Phys Chem C 114:17989

    Article  CAS  Google Scholar 

  11. Zheng Zh, Zhang ShQ, Zhang MJ, Zhao K, Ye L, Chen Y, Yang B, Hou JH (2014) Adv Mater. doi:10.1002/adma.201404525

    Google Scholar 

  12. Zhang ZH, Peng B, Liu B, Pan CY, Li YF, He YH, Zhou KC, Zou YP (2010) Polym Chem 1:1441

    Article  CAS  Google Scholar 

  13. Zou YP, Najari A, Berrouard P, Beaupré S, Aich RB, Tao Y, Leclerc M (2010) J Am Chem Soc 132:5330

    Article  CAS  Google Scholar 

  14. He ZC, Zhong CG, Su SJ, Xu M, Wu HB, Cao Y (2012) Nat Photonics 6:591

    Google Scholar 

  15. Bunz H (2010) Angew Chem Int Ed 49:5037

    Article  CAS  Google Scholar 

  16. Liu B, Chen XW, Zou YP, Xiao L, Xu XJ, He YH, Li LD, Li YF (2012) Macromolecules 45:6898

    Article  CAS  Google Scholar 

  17. Huang F, Hou L, Shen H, Yang R, Hou Q, Cao Y (2006) J Polym Sci, Part A: Polym Chem 44:2521

    Article  CAS  Google Scholar 

  18. Hou J, Park MH, Zhang S, Yao Y, Chen LM, Li JH, Yang Y (2008) Macromolecules 41:6012

    Article  CAS  Google Scholar 

  19. Chen XW, Liu B, Zou YP, Xiao L, Guo XP, He YH, Li YF (2012) J Mater Chem 22:17724

    Article  CAS  Google Scholar 

  20. Helgesen M, Gevorgyan SA, Krebs FC, Janssen RA (2009) Chem Mater 21:4669

    Article  CAS  Google Scholar 

  21. Zhou E, Yamakawa S, Zhang Y, Tajima K, Yang C, Hashimoto K (2009) J Mater Chem 19:7730

    Article  CAS  Google Scholar 

  22. Lee WH, Son SK, Kim K, Lee SK, Shin WS, Moon S, Kang IN (2012) Macromolecules 45:1303

    Article  CAS  Google Scholar 

  23. Malliaras GG, Salem JR, Brock PJ, Scott C (1998) Phys Rev B 58:13411

    Article  Google Scholar 

  24. Zhang J, Cai WZ, Huang F, Wang EG, Zhong CM, Liu SJ, Wang M, Duan CH, Yang TB, Cao Y (2011) Macromolecules 44:894

    Article  CAS  Google Scholar 

  25. Li W, Zhou Y, Andersson BV, Andersson LM, Thomann Y, Veit C, Tvingstedt K, Qin R, Bo Z, Inganas O, Wurfel U, Zhang F (2011) Org Electron 12:1544

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Open-End Fund for the Valuable and Precision Instruments of Central South University. The NMR data are characterized by Modern Analysis and testing Center of Central South University.

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    Authors and Affiliations

    1. College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, China

      Weifang Liu, Lixia Qiu, Wangjun Tang, Lihui Jiang, Hongjian Peng, Guohui Chen, Xuxian Xiao & Yingping Zou

    2. State Key Laboratory of Molecular Engineering of Polymers, Fudan University, Shanghai, 200433, China

      Lihui Jiang

    3. School of Physics and Electronics, Central South University, Changsha, 410083, China

      Lihui Jiang & Yingping Zou

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    1. Weifang Liu
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    2. Lixia Qiu
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    Correspondence to Lihui Jiang or Xuxian Xiao.

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    W. Liu, L. Qiu and W. Tang contributed to this work equally.

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    Liu, W., Qiu, L., Tang, W. et al. Synthesis and characterization of 5,6-bis(n-octyloxy)[2,1,3] selenadiazole-based polymers for photovoltaic applications. Polym. Bull. 73, 385–398 (2016). https://doi.org/10.1007/s00289-015-1493-2

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    • DOI: https://doi.org/10.1007/s00289-015-1493-2

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