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Synthesis and Photovoltaic Properties of Simple Fluorene-Based Triphenylamine Metal-Free Organic Sensitizers for Dye-Sensitized Solar Cells

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Abstract

Two novel metal-free organic dyes, TM-a and TM-b derived from triphenylamine have been successfully synthesized and characterized. These D-π-A sensitizers feature triphenylamine as an electron donor, fluorene and thiophene as π-bridges, and 2-cyanoacrylic acid as both an acceptor and an anchor. This architecture allows a deeper insight into the effect of modification of the properties of D-π-A sensitizers, which is beneficial to improve their performance of in dye-sensitized solar cells (DSSCs). Both the TM-a and TM-b dyes displayed maximum absorption in the visible region at 457 and 454 nm, respectively. The DSSCs based on TM-a exhibited a superior photoelectric conversion efficiency, along with higher open-circuit voltage and short-circuit current (η 2.91%, VOC 657 mV, JSC 6.81 mA cm–2, and FF 0.65). These results indicate that the dye, with triphenylamine as an electron donor and fluorene as a π-linker, is a highly promising candidate for efficient DSSC applications.

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REFERENCES

  1. Oregan, B. and Gratzel, M., Nature, 1991, vol. 353, p. 737. https://doi.org/10.1038/353737a0

    Article  CAS  Google Scholar 

  2. Nazeeruddin, M.K., Baranoff, E., and Graetzel, M., Sol. Energy, 2011, vol. 85, p. 1172. https://doi.org/10.1016/j.solener.2011.01.018

    Article  CAS  Google Scholar 

  3. Verbitskiy, E.V., Rusinov, G.L., Chupakhin, O.N., and Charushin, V.N., Dyes Pigm., 2021, vol. 194. https://doi.org/10.1016/j.dyepig.2021.109650

  4. Hagfeldt, A., Boschloo, G., Sun, L., Kloo, L., and Pettersson, H., Chem. Rev., 2010, vol. 110, p. 6595. https://doi.org/10.1021/cr900356p

    Article  CAS  PubMed  Google Scholar 

  5. Lee, C.-P., Lin, R.Y.-Y., Lin, L.-Y., Li, C.-T., Chu, T.-C., Sun, S.-S., Lin, J.T., and Ho, K.-C., RSC Adv., 2015, vol. 5, p. 23810. https://doi.org/10.1039/c4ra16493h

    Article  CAS  Google Scholar 

  6. Han, L., Zu, X., Cui, Y., Wu, H., Ye, Q., and Gao, J., Org. Electron., 2014, vol. 15, p. 1536. https://doi.org/10.1016/j.orgel.2014.04.016

    Article  CAS  Google Scholar 

  7. Ruamyart, C., Chasing, P., Sudyoadsuk, T., Promarak, V., and Ruangsupapichat, N., New J. Chem., 2021, vol. 45, p. 7542. https://doi.org/10.1039/d0nj06256a

    Article  CAS  Google Scholar 

  8. Tanaka, E., Mikhailov, M.S., Gudim, N.S., Knyazeva, E.A., Mikhalchenko, L.V., Robertson, N., and Rakitin, O.A., Mol. Syst. Design Eng., 2021, vol. 6, p. 730. https://doi.org/10.1039/d1me00054c

    Article  CAS  Google Scholar 

  9. Hua, Y., Chang, S., He, J., Zhang, C., Zhao, J., Chen, T., Wong, W.-Y., Wong, W.-K., and Zhu, X., Chem. Eur. J., 2014, vol. 20, p. 6300. https://doi.org/10.1002/chem.201304897

    Article  CAS  PubMed  Google Scholar 

  10. Hara, K., Sato, T., Katoh, R., Furube, A., Ohga, Y., Shinpo, A., Suga, S., Sayama, K., Sugihara, H., and Arakawa, H., J. Phys. Chem. B, 2003, vol. 107, p. 597. https://doi.org/10.1021/jp026963x

    Article  CAS  Google Scholar 

  11. Wang, Z. S., Hara, K., Dan-Oh, Y., Kasada, C., Shinpo, A., Suga, S., Arakawa, H., and Sugihara, H., J. Phys. Chem. B, 2005, vol. 109, p. 3907. https://doi.org/10.1021/jp044851v

    Article  CAS  PubMed  Google Scholar 

  12. Hara, K., Wang, Z. S., Sato, T., Furube, A., Katoh, R., Sugihara, H., Dan-Oh, Y., Kasada, C., Shinpo, A., and Suga, S., J. Phys. Chem. B, 2005, vol. 109, p. 15476. https://doi.org/10.1021/jp0518557

    Article  CAS  PubMed  Google Scholar 

  13. Li, R., Lv, X., Shi, D., Zhou, D., Cheng, Y., Zhang, G., and Wang, P., J. Phys. Chem. C, 2009, vol. 113, p. 7469. https://doi.org/10.1021/jp900972v

    Article  CAS  Google Scholar 

  14. Yang, F., Akhtaruzzaman, M., Islam, A., Jin, T., El-Shafei, A., Qin, C., Han, L., Alamry, K.A., Kosa, S.A., Hussein, M.A., Asiri, A.M., and Yamamoto, Y., J. Mater. Chem., 2012, vol. 22, p. 22550. https://doi.org/10.1039/c2jm34363k

    Article  CAS  Google Scholar 

  15. Koumura, N., Wang, Z.-S., Mori, S., Miyashita, M., Suzuki, E., and Hara, K., J. Am. Chem. Soc., 2006, vol. 128, p. 14256. https://doi.org/10.1021/ja0645640

    Article  CAS  PubMed  Google Scholar 

  16. Wang, Z.-S., Koumura, N., Cui, Y., Takahashi, M., Sekiguchi, H., Mori, A., Kubo, T., Furube, A., and Hara, K., Chem. Mater., 2008, vol. 20, p. 3993. https://doi.org/10.1021/cm8003276

    Article  CAS  Google Scholar 

  17. Teng, C., Yang, X., Yang, C., Li, S., Cheng, M., Hagfeldt, A., and Sun, L., J. Phys. Chem. C, 2010, vol. 114, p. 9101. https://doi.org/10.1021/jp101238k

    Article  CAS  Google Scholar 

  18. May, L., Daniel, S., and Mueller, T.J.J., Org. Chem. Front., 2020, vol. 7, p. 329. https://doi.org/10.1039/c9qo01318k

    Article  CAS  Google Scholar 

  19. Demeter, D., Melchiorre, F., Biagini, P., Po, R., and Roncali, J., Tetrahedron Lett., 2016, vol. 57, p. 505. https://doi.org/10.1016/j.tetlet.2015.12.077

    Article  CAS  Google Scholar 

  20. Zhang, X., Pei, X., Liao, C., and Zou, L., Res. Chem. Intermed., 2017, vol. 43, p. 2737. https://doi.org/10.1007/s11164-016-2792-4

    Article  CAS  Google Scholar 

  21. Wan, Z., Jia, C., Wang, Y., and Yao, X., ACS Appl. Mater. Interfaces, 2017, vol. 9, p. 25225. https://doi.org/10.1021/acsami.7b04233

    Article  CAS  PubMed  Google Scholar 

  22. Zhang, L. and Cole, J.M., ACS Appl. Mater. Interfaces, 2015, vol. 7, p. 3427. https://doi.org/10.1021/am507334m

    Article  CAS  PubMed  Google Scholar 

  23. Ahmad, S., Guillen, E., Kavan, L., Graetzel, M., and Nazeeruddin, M.K., Energy Environ. Sci., 2013, vol. 6, p. 3439. https://doi.org/10.1039/c3ee41888j

    Article  CAS  Google Scholar 

  24. Roohi, H. and Motamedifar, N., Mol. Phys., 2021, vol. 119. https://doi.org/10.1080/00268976.2021.1913250

  25. Pecnikaj, I., Minudri, D., Otero, L., Fungo, F., Cavazzini, M., Orlandi, S., and Pozzi, G., New J. Chem., 2017, vol. 41, p. 7729. https://doi.org/10.1039/c7nj01516j

    Article  CAS  Google Scholar 

  26. Tsuchiya, M., Sakamoto, R., Shimada, M., Yamanoi, Y., Hattori, Y., Sugimoto, K., Nishibori, E., and Nishihara, H., Chem. Commun., 2017, vol. 53, p. 7509. https://doi.org/10.1039/c7cc03279j

    Article  CAS  Google Scholar 

  27. Kim, S., Song, K.H., Kang, S.O., and Ko, J., Chem. Commun., 2004, p. 68. https://doi.org/10.1039/b312028g

  28. Shirota, Y., Kinoshita, M., Noda, T., Okumoto, K., and Ohara, T., J. Am. Chem. Soc., 2000, vol. 122, p. 11021. https://doi.org/10.1021/ja0023332

    Article  CAS  Google Scholar 

  29. Tan, C.-J., Yang, C.-S., Sheng, Y.-C., Amini, H.W., and Tsai, H.-H.G., J. Phys. Chem. C, 2016, vol. 120, p. 21272. https://doi.org/10.1021/acs.jpcc.6b07032

    Article  CAS  Google Scholar 

  30. Capodilupo, A. L., Giannuzzi, R., Corrente, G. A., De Marco, L., Fabiano, E., Cardone, A., Gigli, G., and Ciccarella, G., Tetrahedron, 2016, vol. 72, p. 5788. https://doi.org/10.1016/j.tet.2016.08.006

    Article  CAS  Google Scholar 

  31. Massin, J., Ducasse, L., Abbas, M., Hirsch, L., Toupance, T., and Olivier, C., Dyes Pigm., 2015, vol. 118, p. 76. https://doi.org/10.1016/j.dyepig.2015.02.020

    Article  CAS  Google Scholar 

  32. Siu, C.-H., Lee, L. T. L., Ho, P.-Y., Majumdar, P., Ho, C.-L., Chen, T., Zhao, J., Li, H., and Wong, W.-Y., J. Mater. Chem. C, 2014, vol. 2, p. 7086. https://doi.org/10.1039/c4tc00661e

    Article  CAS  Google Scholar 

  33. Venkateswararao, A., Thomas, K.R.J., Li, C.-T., and Ho, K.-C., RSC Adv., 2015, vol. 5, p. 17953. https://doi.org/10.1039/c4ra15234d

    Article  CAS  Google Scholar 

  34. Dai, X.-X., Feng, H.-L., Huang, Z.-S., Wang, M.-J., Wang, L., Kuang, D.-B., Meier, H., and Cao, D., Dyes Pigm., 2015, vol. 114, p. 47 https://doi.org/10.1016/j.dyepig.2014.10.016

    Article  CAS  Google Scholar 

  35. Hou, Y., Liu, J., Zhang, N., and Zhao, J., J. Phys. Chem. A, 2020, vol. 124, p. 9360. https://doi.org/10.1021/acs.jpca.0c07907

    Article  CAS  PubMed  Google Scholar 

  36. Xue, P., Chen, P., Jia, J., Xu, Q., Sun, J., Yao, B., Zhang, Z., and Lu, R., Chem. Commun., 2014, vol. 50, p. 2569. https://doi.org/10.1039/C3CC49208G

    Article  CAS  Google Scholar 

  37. Mizusaki, M., Yamada, Y., Obara, S., and Tada, K., Chem. Lett., 2012, vol. 41, p. 516. https://doi.org/10.1246/cl.2012.516

    Article  CAS  Google Scholar 

  38. Homnick, P.J. and Lahti, P.M., Phys. Chem. Chem. Phys., 2012, vol. 14, p. 11961. https://doi.org/10.1039/C2CP41813D

    Article  CAS  PubMed  Google Scholar 

  39. Zhao, Y., Chen, H., Yin, L., Cheng, X., Zhang, W., and Zhu, X., Polym. Chem., 2018, vol. 9, p. 2295. https://doi.org/10.1039/C8PY00114F

    Article  CAS  Google Scholar 

  40. Li, J.H., Deng, C.L., and Xie, Y.X., Synth. Commun., 2007, vol. 37, p. 2433 https://doi.org/10.1080/00397910701412828

    Article  CAS  Google Scholar 

  41. Alifu, N., Yan, L., Zhang, H., Zebibula, A., Zhu, Z., Xi, W., Roe, A.W., Xu, B., Tian, W., and Qian, J., Dyes Pigm., 2017, vol. 143, p. 76. https://doi.org/10.1016/j.dyepig.2017.04.017

    Article  CAS  Google Scholar 

  42. Chalais, S., Laszlo, P., and Mathy, A., Tetrahedron Lett., 1985, vol. 26, p. 4453. https://doi.org/10.1016/S0040-4039(00)88928-5

    Article  CAS  Google Scholar 

  43. Lin, J.H., Elangovan, A., and Ho, T.I., J. Org. Chem., 2005, vol. 70, p. 7397. https://doi.org/10.1021/jo051183g

    Article  CAS  PubMed  Google Scholar 

  44. Stokes, G.G., Philos. Trans. R. Soc., 1852, vol. 142, p. 463. https://doi.org/10.1098/rstl.1852.0022

    Article  Google Scholar 

  45. Gagne, R.R., Koval, C.A., and Lisensky, G.C., Inorg. Chem., 1980, vol. 19, p. 2854. https://doi.org/10.1021/ic50211a080

    Article  CAS  Google Scholar 

  46. Hagberg, D.P., Edvinsson, T., Marinado, T., Boschloo, G., Hagfeldt, A., and Sun, L., Chem. Commun., 2006, p. 2245, https://doi.org/10.1039/b603002e

  47. Hagfeldt, A. and Gratzel, M., Chem. Rev., 1995, vol. 95, p. 49. https://doi.org/10.1021/cr00033a003

    Article  CAS  Google Scholar 

  48. Pastore, M. and De Angelis, F., ACS Nano, 2010, vol. 4, p. 556. https://doi.org/10.1021/nn901518s

    Article  CAS  PubMed  Google Scholar 

  49. Hsiao, S.H., Wang, H.M., Chang, P.C., Kung, Y.R., and Lee, T.M., J. Polym. Sci. A Polym. Chem., 2013, vol. 51, p. 2925. https://doi.org/10.1002/pola.26686

    Article  CAS  Google Scholar 

  50. Hariharan, P., Moon, D., and Anthony, S.P., CrystEngComm, 2017, vol. 19, p. 6489. https://doi.org/10.1039/C7CE01650F

    Article  CAS  Google Scholar 

  51. Wang, J. and Rueck-Braun, K., ChemPhotoChem, 2017, vol. 1, p. 493. https://doi.org/10.1002/cptc.201700103

    Article  CAS  Google Scholar 

  52. Ji, L., Fang, Q., Yuan, M.-s., Liu, Z.-q., Shen, Y.-x., and Chen, H.-f., Org. Lett., 2010, vol. 12, p. 5192. https://doi.org/10.1021/ol102057t

    Article  CAS  PubMed  Google Scholar 

  53. Liedtke, A., O’Neill, M., Wertmöller, A., Kitney, S.P., and Kelly, S.M., Chem. Mater., 2008, vol. 20, p. 3579. https://doi.org/10.1021/cm702925f

    Article  CAS  Google Scholar 

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Funding

This study is supported by the Fundamental Research Funds for the Central Universities (no. 20720170039).

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Authors and Affiliations

  1. Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, 361005, Xiamen, China

    Chen-Jie Li, Jie Zhang, Zi-Long Huang, Yu-Xing Gao, Li-Yi Ye, Ying-Wu Yin & Song Tu

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  1. Chen-Jie Li
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Li, CJ., Zhang, J., Huang, ZL. et al. Synthesis and Photovoltaic Properties of Simple Fluorene-Based Triphenylamine Metal-Free Organic Sensitizers for Dye-Sensitized Solar Cells. Russ J Org Chem 59, 312–323 (2023). https://doi.org/10.1134/S1070428023020136

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