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Branched dibenzofulvene-based organic dyes for dye-sensitized solar cells under one sun and dim light

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Abstract

Series of metal-free dyes (OMS4-7) featuring a dibenzofulvene connected with thienyl or furanyl as conjugation bridge, T-shaped diarylamines (diphenylamine or phenyl-1-naphthylamine) as donors and different numbers of cyanoacrylic acid as anchors have been synthesized and applied into dye-sensitized solar cells (DSSCs). The efects of different donors, conjuation segments and number of anchors on optical and photovoltaic properties were investigated through photophysics, electrochemical and photovoltaic measurements. Of the DSSCs, the structure contains mono anchor with thienyl dibenzofulvene linked to diphenylamine, i.e. OMS4-based device exhibited the highest power conversion efficiency (PCE) of 2.42%, a value of Jsc of 6.01 mA cm−2, a Voc of 0.63 V, and a fill factor of 0.63 under 10 mM CDA co-adsorbent and AM 1.5 irradiation. The corresponding device was also conducted with respect to different light intensity such as D65, CWF and TL84. As a result, the cell performance based on TL84 with 2500 lx exhibited the best PCE of 8.78%.

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References

  1. B. O’Reagen, M. Grätzel, A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature 353, 737–740 (1991)

    Article  Google Scholar 

  2. M. Grätzel, Recent advances in sensitized mesoscopic solar cells. Acc. Chem. Res. 42, 1788–1798 (2009)

    Article  Google Scholar 

  3. M.B. Desta, N.S. Vinh, C.H.P. Kumar, S. Chaurasia, W.T. Wu, J.T. Lin, T.C. Wei, E.W.G. Diau, Pyrazine-incorporating panchromatic sensitizers for dye sensitized solar cells under one sun and dim light. J. Mater. Chem. A 6, 13778–13789 (2018)

    Article  Google Scholar 

  4. K.S.K. Reddy, Y.C. Liu, H.H. Chou, K. Kala, T.C. Wei, C.Y. Yeh, Synthesis and characterization of novel β-bis(N, N-diarylamino)-substituted porphyrin for dye-sensitized solar cells under 1 sun and dim light conditions. ACS Appl. Mater. Interfaces. 10, 39970–39982 (2018)

    Article  Google Scholar 

  5. A. Hagfeldt, G. Boschloo, L.C. Sun, L. Kloo, H. Pettersson, Dye-sensitized solar cells. Chem. Rev. 110, 6595–6663 (2010)

    Article  Google Scholar 

  6. C.Y. Chen, M. Wang, J.Y. Li, N. Pootrakulchote, L. Alibabaei, C.H. Ngoc-Le, J.D. Decoppet, J.H. Tsai, C. Grätzel, C.G. Wu, S.M. Zakeeruddin, M. Grätzel, Highly efficient light-harvesting ruthenium sensitizer for thin-film dye-sensitized solar cells. ACS Nano 3, 3103–3109 (2009)

    Article  Google Scholar 

  7. W.C. Chen, F.T. Kong, Z.Q. Li, J.H. Pan, X.P. Liu, F.L. Guo, L. Zhou, Y. Huang, T. Yu, S.Y. Dai, Superior light-harvesting heteroleptic ruthenium (II) complexes with electron-donating antennas for high performance dye-sensitized solar cells. ACS Appl. Mater. Interfaces. 8, 19410–19417 (2016)

    Article  Google Scholar 

  8. M. Urbani, M. Grätzel, M.K. Nazeeruddin, T. Torres, Meso-substituted porphyrins for dye-sensitized solar cells. Chem. Rev. 114, 12330–12396 (2014)

    Article  Google Scholar 

  9. K. Kakiage, Y. Aoyama, T. Yano, K. Oya, J.I. Fujisawa, M. Hanaya, Highly-efficient dye-sensitized solar cells with collaborative sensitization by silyl-anchor and carboxy-anchor dyes. Chem. Commun. 51, 15894–15897 (2015)

    Article  Google Scholar 

  10. Y.K. Eom, I.T. Choi, S.H. Kang, J. Lee, J. Kim, M.J. Ju, H.K. Kim, Thieno[3,2‐b][1]benzothiophene derivative as a new π‐bridge unit in D–π–A structural organic sensitizers with over 10.47% efficiency for dye‐sensitized solar cells. Adv. Energy Mater. 5, 1500300 (2015)

    Article  Google Scholar 

  11. Z. Yao, H. Wu, Y. Li, J. Wang, J. Zhang, M. Zhang, Y. Guo, P. Wang, Dithienopicenocarbazole as the kernel module of low-energy-gap organic dyes for efficient conversion of sunlight to electricity. Energy Environ. Sci. 8, 3192–3197 (2015)

    Article  Google Scholar 

  12. A. Mishra, M.K.R. Fischer, P. Bäuerle, Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules. Angew. Chem. Int. Ed. 48, 2474–2499 (2009)

    Article  Google Scholar 

  13. Y.S. Yen, H.H. Chou, Y.C. Chen, C.Y. Hsu, J.T. Lin, Recent developments in molecule-based organic materials for dye-sensitized solar cells. J. Mater. Chem. 22, 8734–8747 (2012)

    Article  Google Scholar 

  14. S. Ahmad, E. Guillén, L. Kavan, M. Grätzel, M.K. Nazeeruddin, Metal free sensitizer and catalyst for dye sensitized solar cells. Energy Environ. Sci. 6, 3439–3466 (2013)

    Article  Google Scholar 

  15. N. Manfredi, B. Cecconi, A. Abbotto, Multi-branched multi-anchoring metal-free dyes for dye-sensitized solar cells. Eur. J. Org. Chem. 2014, 7069–7086 (2014)

    Article  Google Scholar 

  16. Y.C. Chen, J.T. Lin, Multi-anchored sensitizers for dye-sensitized solar cells. Sustain. Energy Fuels 1, 969–985 (2017)

    Article  Google Scholar 

  17. A. Peddapuram, H. Cheema, R.E. Adams, R.H. Schmehl, J.H. Delcamp, A stable panchromatic green dual acceptor, dual donor organic dye for dye-sensitized solar cells. J. Phys. Chem. C 121, 8770–8780 (2017)

    Article  Google Scholar 

  18. H. Meier, Z.S. Huang, D. Cao, Double D–π–A branched dyes – a new class of metal-free organic dyes for efficient dye-sensitized solar cells. J. Mater. Chem. C 5, 9828–9837 (2017)

    Article  Google Scholar 

  19. W. Li, Y. Wu, X. Li, Y. Xie, W. Zhu, Absorption and photovoltaic properties of organic solar cell sensitizers containing fluorene unit as conjunction bridge. Energy Environ. Sci. 4, 1830–1837 (2011)

    Article  Google Scholar 

  20. S. Chaurasia, Y.C. Chen, H.H. Chou, Y.S. Wen, J.T. Lin, Coplanar indenofluorene-based organic dyes for dye-sensitized solar cells. Tetrahedron 68, 7755–7762 (2012)

    Article  Google Scholar 

  21. Y. Bai, J. Zhang, D. Zhou, Y. Wang, M. Zhang, P. Wang, Engineering organic sensitizers for iodine-free dye-sensitized solar cells: red-shifted current response concomitant with attenuated charge recombination. J. Am. Chem. Soc. 133, 11442–11445 (2011)

    Article  Google Scholar 

  22. C. Du, C. Li, W. Li, X. Chen, Z. Bo, C. Veit, Z. Ma, U. Wuerfel, H. Zhu, W. Hu, F. Zhang, 9-Alkylidene-9H-fluorene-containing polymer for high-efficiency polymer solar cells. Macromolecules 44, 7617–7624 (2011)

    Article  Google Scholar 

  23. H. Li, R. Tang, Y. Hou, Y. Yang, J. Chen, L. Liu, H. Han, T. Peng, Q. Li, Z. Li, Diphenyldibenzofulvene-based sensitizers for efficient dye-sensitized solar cells: the tuned absorption properties and partially suppressed aggregation. Asian J. Org. Chem. 3, 176–184 (2014)

    Article  Google Scholar 

  24. A.L. Capodilupo, L. De Marco, E. Fabiano, R. Giannuzzi, A. Scrascia, C. Clarlucci, G.A. Corrente, M.P. Cipolla, G. Gigli, G. Ciccarella, New organic dyes based on a dibenzofulvene bridge for highly efficient dye-sensitized solar cells. J. Mater. Chem. A 2, 14181–14188 (2014)

    Article  Google Scholar 

  25. A.L. Capodilupo, L. De Marco, G.A. Corrente, R. Giannuzzi, E. Fabiano, A. Cardone, G. Gigli, G. Ciccarella, Synthesis and characterization of a new series of dibenzofulvene based organic dyes for DSSCs. Dyes Pigments 13, 79–89 (2016)

    Article  Google Scholar 

  26. A.L. Capodilupo, R. Giannuzzi, G.A. Corrente, L. De Marco, E. Fabiano, A. Cardone, G. Gigli, G. Ciccarella, Synthesis and photovoltaic performance of dibenzofulvene-based organic sensitizers for DSSC. Tetrahedron 72, 5788–5797 (2016)

    Article  Google Scholar 

  27. G.A. Corrente, E. Fabiano, L. De Marco, G. Accorsi, R. Giannuzzi, A. Cardone, G. Gigli, G. Ciccarella, A.L. Capodilupo, Effects of donor position on dibenzofulvene-based organic dyes for photovoltaics. J. Mater. Sci.: Mater. Electron. 28(12), 8694–8707 (2017)

    Google Scholar 

  28. J.T. Lin, P.C. Chen, Y.S. Yen, Y.C. Hsu, H.H. Chou, M.C.P. Yeh, Organic dyes containing furan moiety for high-performance dye-sensitized solar cells. Org. Lett. 11, 97–100 (2009)

    Article  Google Scholar 

  29. O. Gidron, M. Bendikov, α-Oligofurans: an emerging class of conjugated oligomers for organic electronics. Angew. Chem. Int. Ed. 53, 2546–2555 (2014)

    Article  Google Scholar 

  30. W. Jiang, Y. Sun, X. Wang, Q. Wang, W. Xu, Synthesis and photochemical properties of novel 4-diarylamine-1,8-naphthalimide derivatives. Dyes Pigments 77, 125–128 (2008)

    Article  Google Scholar 

  31. R.Y.Y. Lin, F.L. Wu, C.H. Chang, H.H. Chou, T.M. Chuang, T.C. Chu, C.Y. Hsu, P.W. Chen, K.C. Ho, Y.H. Lo, J.T. Lin, Y-shaped metal-free D–π–(A)2 sensitizers for high-performance dye-sensitized solar cells. J. Mater. Chem. A 2, 3092–3101 (2014)

    Article  Google Scholar 

  32. Z.S. Wang, H. Kawauchi, T. Kashima, H. Arakawa, Significant influence of TiO2 photoelectrode morphology on the energy conversion efficiency of N719 dye-sensitized solar cell. Coord. Chem. Rev. 248, 1381–1389 (2004)

    Article  Google Scholar 

  33. M. Nomura, K. Fukukawa, Y. Shibasaki, M. Ueda, New amorphous hole-transporting molecular materials: 1,1,1-Tris(4-(4-diarylaminobenzoyloxy)phenyl)ethane. Synth. Met. 132, 9–13 (2002)

    Article  Google Scholar 

  34. A. Baheti, K.R.J. Thomas, C.P. Lee, K.C. Ho, Synthesis and characterization of dianchoring organic dyes containing 2, 7-diaminofluorene donors as efficient sensitizers for dye-sensitized solar cells. Org. Electron. 14, 3267–3276 (2013)

    Article  Google Scholar 

  35. Y. Shao, L.F. Molnar, Y. Jung, J. Kussmann, C. Ochsenfeld, S.T. Brown, A.T. Gilbert, L.V. Slipchenko, S.V. Levchenko, D.P. O’Neill, R.A. DiStasio Jr., Advances in methods and algorithms in a modern quantum chemistry program package. Phys. Chem. Chem. Phys. 8(27), 3172–3191 (2006)

    Article  Google Scholar 

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Acknowledgements

Financial support from the Ministry of Science and Technology (Grant Nos. MOST 106-2221-E-151-046 -MY2 and MOST 106-2113-M-029-001) Taiwan ROC is gratefully acknowledged.

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Correspondence to Yung-Chung Chen or Yuan-Jay Chang.

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Chen, YC., Huang, GW., Chang, YJ. et al. Branched dibenzofulvene-based organic dyes for dye-sensitized solar cells under one sun and dim light. J Mater Sci: Mater Electron 30, 12981–12991 (2019). https://doi.org/10.1007/s10854-019-01660-y

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