Skip to main content
Log in

A-D-A small molecule donors based on pyrene and diketopyrrolopyrrole for organic solar cells

  • Articles
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

Three new electron donating small molecules (SMs), Pyr(EH-DPP)2, Pyr(HD-DPP)2 and PyrA(EH-DPP)2, are designed and synthesized through coupling electron rich pyrene core with electron deficient diketopyrrolopyrrole (DPP) terminals, of which the derived organic solar cells (OSCs) exhibit interesting structure-performance correlation. It shows that the tune of their solubilizing side chains and π-bridge for the acceptor-donor-acceptor (A-D-A) SMs can significantly alter the resultant short-circuit current density and power conversion efficiency (PCE) in OSCs. The Pyr(EH-DPP)2 with short side chains displays broader absorption and higher hole mobility than the Pyr(HD-DPP)2 with long side chains. Although showing planar structure, the acetylene bridge-incorporated PyrA(EH-DPP)2 adapts an undesired edge-on packing and strong aggregation in film, leading to non-ideal morphology and poor miscibility with fullerene acceptors. As a result, the PCE of the solar cell based on Pyr(EH-DPP)2 is several times higher than those based on Pyr(HD-DPP)2 and PyrA(EH-DPP)2, indicating the A-D-A combination of polyaromatics with DPP would be the promising skeleton for developing photovoltaic semiconductors.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. He Z, Xiao B, Liu F, Wu H, Yang Y, Xiao S, Wang C, Russell TP, Cao Y. Nat Photon, 2015, 9: 174–179

    Article  CAS  Google Scholar 

  2. Liu Y, Zhao J, Li Z, Mu C, Ma W, Hu H, Jiang K, Lin H, Ade H, Yan H. Nat Commun, 2014, 5: 5293

    Article  CAS  Google Scholar 

  3. Li CZ, Chang CY, Zang Y, Ju HX, Chueh CC, Liang PW, Cho N, Ginger DS, Jen AKY. Adv Mater, 2014, 26: 6262–6267

    Article  CAS  Google Scholar 

  4. Zhao W, Li S, Zhang S, Liu X, Hou J. Adv Mater, 2017, 29: 1604059

    Article  Google Scholar 

  5. Kumari T, Lee SM, Kang SH, Chen S, Yang C. Energy Environ Sci, 2017, 10: 258–265

    Article  CAS  Google Scholar 

  6. Yang Y, Zhang ZG, Bin H, Chen S, Gao L, Xue L, Yang C, Li Y. J Am Chem Soc, 2016, 138: 15011–15018

    Article  CAS  Google Scholar 

  7. Zhang S, Ye L, Zhao W, Yang B, Wang Q, Hou J. Sci China Chem, 2015, 58: 248–256

    Article  CAS  Google Scholar 

  8. Li Y. Sci China Chem, 2015, 58: 191

    Article  CAS  Google Scholar 

  9. Zhao W, Zhang S, Hou J. Sci China Chem, 2016, 59: 1574–1582

    Article  CAS  Google Scholar 

  10. Zhang S, Zuo L, Chen J, Zhang Z, Mai J, Lau TK, Lu X, Shi M, Chen H. J Mater Chem A, 2016, 4: 1702–1707

    Article  CAS  Google Scholar 

  11. Zhang Q, Kan B, Liu F, Long G, Wan X, Chen X, Zuo Y, Ni W, Zhang H, Li M, Hu Z, Huang F, Cao Y, Liang Z, Zhang M, Russell TP, Chen Y. Nat Photon, 2014, 9: 35–41

    Article  Google Scholar 

  12. He Z, Zhong C, Su S, Xu M, Wu H, Cao Y. Nat Photon, 2012, 6: 593–597

    Article  CAS  Google Scholar 

  13. Jin Y, Chen Z, Dong S, Zheng N, Ying L, Jiang XF, Liu F, Huang F, Cao Y. Adv Mater, 2016, 28: 9811–9818

    Article  CAS  Google Scholar 

  14. Fan B, Sun C, Jiang XF, Zhang G, Chen Z, Ying L, Huang F, Cao Y. Adv Funct Mater, 2016, 26: 6479–6488

    Article  CAS  Google Scholar 

  15. Zhou C, Zhang G, Zhong C, Jia X, Luo P, Xu R, Gao K, Jiang X, Liu F, Russell TP, Huang F, Cao Y. Adv Energy Mater, 2017, 7: 1601081

    Article  Google Scholar 

  16. Lin Y, Zhao F, Wu Y, Chen K, Xia Y, Li G, Prasad SKK, Zhu J, Huo L, Bin H, Zhang ZG, Guo X, Zhang M, Sun Y, Gao F, Wei Z, Ma W, Wang C, Hodgkiss J, Bo Z, Inganäs O, Li Y, Zhan X. Adv Mater, 2017, 29: 1604155

    Article  Google Scholar 

  17. Coughlin JE, Henson ZB, Welch GC, Bazan GC. Acc Chem Res, 2014, 47: 257–270

    Article  CAS  Google Scholar 

  18. Wang JL, Wu Z, Miao JS, Liu KK, Chang ZF, Zhang RB, Wu HB, Cao Y. Chem Mater, 2015, 27: 4338–4348

    Article  CAS  Google Scholar 

  19. Intemann JJ, Yao K, Ding F, Xu Y, Xin X, Li X, Jen AKY. Adv Funct Mater, 2015, 25: 4889–4897

    Article  CAS  Google Scholar 

  20. Roncali J, Leriche P, Blanchard P. Adv Mater, 2014, 26: 3821–3838

    Article  CAS  Google Scholar 

  21. Kan B, Zhang Q, Li M, Wan X, Ni W, Long G, Wang Y, Yang X, Feng H, Chen Y. J Am Chem Soc, 2014, 136: 15529–15532

    Article  CAS  Google Scholar 

  22. Sun K, Xiao Z, Lu S, Zajaczkowski W, Pisula W, Hanssen E, White JM, Williamson RM, Subbiah J, Ouyang J, Holmes AB, Wong WWH, Jones DJ. Nat Commun, 2015, 6: 6013

    Article  CAS  Google Scholar 

  23. Kan B, Li M, Zhang Q, Liu F, Wan X, Wang Y, Ni W, Long G, Yang X, Feng H, Zuo Y, Zhang M, Huang F, Cao Y, Russell TP, Chen Y. J Am Chem Soc, 2015, 137: 3886–3893

    Article  CAS  Google Scholar 

  24. Liu SY, Fu WF, Xu JQ, Fan CC, Jiang H, Shi M, Li HY, Chen JW, Cao Y, Chen HZ. Nanotechnology, 2014, 25: 014006

    Article  Google Scholar 

  25. Liu SY, Liu WQ, Xu JQ, Fan CC, Fu WF, Ling J, Wu JY, Shi MM, Jen AKY, Chen HZ. ACS Appl Mater Interfaces, 2014, 6: 6765–6775

    Article  CAS  Google Scholar 

  26. Chen M, Fu W, Shi M, Hu X, Pan J, Ling J, Li H, Chen H. J Mater Chem A, 2013, 1: 105–111

    Article  CAS  Google Scholar 

  27. Tang A, Zhan C, Yao J. Adv Energy Mater, 2015, 5: 1500059

    Article  Google Scholar 

  28. Qin H, Li L, Guo F, Su S, Peng J, Cao Y, Peng X. Energy Environ Sci, 2014, 7: 1397–1401

    Article  CAS  Google Scholar 

  29. Wang JL, Xiao F, Yan J, Wu Z, Liu KK, Chang ZF, Zhang RB, Chen H, Wu HB, Cao Y. Adv Funct Mater, 2016, 26: 1803–1812

    Article  CAS  Google Scholar 

  30. Tang A, Zhan C, Yao J, Zhou E. Adv Mater, 2017, 29: 1600013

    Article  Google Scholar 

  31. Shi H, Fu W, Shi M, Ling J, Chen H. J Mater Chem A, 2015, 3: 1902–1905

    Article  CAS  Google Scholar 

  32. Li W, Hendriks KH, Wienk MM, Janssen RAJ. Acc Chem Res, 2016, 49: 78–85

    Article  CAS  Google Scholar 

  33. Choi YS, Jo WH. Org Electron, 2013, 14: 1621–1628

    Article  CAS  Google Scholar 

  34. Duan X, Xiao M, Chen J, Wang X, Peng W, Duan L, Tan H, Lei G, Yang R, Zhu W. ACS Appl Mater Interfaces, 2015, 7: 18292–18299

    Article  CAS  Google Scholar 

  35. Chen J, Duan L, Xiao M, Wang Q, Liu B, Xia H, Yang R, Zhu W. J Mater Chem A, 2016, 4: 4952–4961

    Article  CAS  Google Scholar 

  36. Lin Y, Ma L, Li Y, Liu Y, Zhu D, Zhan X. Adv Energy Mater, 2013, 3: 1166–1170

    Article  CAS  Google Scholar 

  37. Bai H, Cheng P, Wang Y, Ma L, Li Y, Zhu D, Zhan X. J Mater Chem A, 2014, 2: 778–784

    Article  CAS  Google Scholar 

  38. Jung M, Seo D, Kwak K, Kim A, Cha W, Kim H, Yoon Y, Ko MJ, Lee DK, Kim JY, Son HJ, Kim BS. Dyes Pigments, 2015, 115: 23–34

    Article  CAS  Google Scholar 

  39. Jung JW, Russell TP, Jo WH. Chem Mater, 2015, 27: 4865–4870

    Article  CAS  Google Scholar 

  40. Harschneck T, Zhou N, Manley EF, Lou SJ, Yu X, Butler MR, Timalsina A, Turrisi R, Ratner MA, Chen LX, Chang RPH, Facchetti A, Marks TJ. Chem Commun, 2014, 50: 4099–4101

    Article  CAS  Google Scholar 

  41. Li L, Huang Y, Peng J, Cao Y, Peng X. J Mater Chem A, 2013, 1: 2144–2150

    Article  CAS  Google Scholar 

  42. Zerdan RB, Shewmon NT, Zhu Y, Mudrick JP, Chesney KJ, Xue J, Castellano RK. Adv Funct Mater, 2014, 24: 5993–6004

    Article  CAS  Google Scholar 

  43. Wu XF, Fu WF, Xu Z, Shi M, Liu F, Chen HZ, Wan JH, Russell TP. Adv Funct Mater, 2015, 25: 5954–5966

    Article  CAS  Google Scholar 

  44. Min J, Luponosov YN, Gerl A, Polinskaya MS, Peregudova SM, Dmitryakov PV, Bakirov AV, Shcherbina MA, Chvalun SN, Grigorian S, Kaush-Busies N, Ponomarenko SA, Ameri T, Brabec CJ. Adv Energy Mater, 2014, 4: 1301234

    Article  Google Scholar 

  45. Lin Y, Zhao F, He Q, Huo L, Wu Y, Parker TC, Ma W, Sun Y, Wang C, Zhu D, Heeger AJ, Marder SR, Zhan X. J Am Chem Soc, 2016, 138: 4955–4961

    Article  CAS  Google Scholar 

  46. Zhao X, Ma L, Zhang L, Wen Y, Chen J, Shuai Z, Liu Y, Zhan X. Macromolecules, 2013, 46: 2152–2158

    Article  CAS  Google Scholar 

  47. Mun JW, Cho I, Lee D, Yoon WS, Kwon OK, Lee C, Park SY. Org Electron, 2013, 14: 2341–2347

    Article  CAS  Google Scholar 

  48. Gao K, Xiao L, Kan Y, Li L, Yan Y, Huang H, Peng J, Cao Y, Peng X. Chin J Chem, 2016, 34: 353–358

    Article  CAS  Google Scholar 

  49. Kan Y, Liu C, Zhang L, Gao K, Liu F, Chen J, Cao Y. J Mater Chem A, 2016, 4: 14720–14728

    Article  CAS  Google Scholar 

  50. Crawford AG, Liu Z, Mkhalid IAI, Thibault MH, Schwarz N, Alcaraz G, Steffen A, Collings JC, Batsanov AS, Howard JAK, Marder TB. Chem Eur J, 2012, 18: 5022–5035

    Article  CAS  Google Scholar 

  51. Yunpeng Q, Long Y, Huili F, Jianhui H. Sci Sin Chim, 2016, 46: 195

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (51473142, 21674093, 21374075), the Major State Basic Research Development Program (2014CB643503), and International Science and Technology Cooperation Program of China (2016YFE0102900).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Chang-Zhi Li, Alex K. -Y. Jen or Hongzheng Chen.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xu, JQ., Liu, W., Liu, SY. et al. A-D-A small molecule donors based on pyrene and diketopyrrolopyrrole for organic solar cells. Sci. China Chem. 60, 561–569 (2017). https://doi.org/10.1007/s11426-016-9003-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-016-9003-9

Keywords

Navigation