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Design and synthesis of novel bichalcophene derivatives with double anchoring groups for dye-sensitized solar cell applications: sensitization and co-sensitization with N-719

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Abstract

Novel dyes F1-3 based on bichalcophene-pyrimidine-2,4,6-trione derivatives with dual anchoring were developed, synthesized, and evaluated as sensitizers and co-sensitizers for dye-sensitized solar cells (DSSCs). F1 displayed the best DSSC performance (η, PCE = 4.41%) and the highest photovoltaic parameters, which were as follows: current density, JSC = 10.66 mA cm−2, photovoltage, VOC = 0.654 V, and fill factor, FF = 64.3%. These findings can be ascribed to F1’s superior optical and electrochemical characteristics when compared to other structures such as F2 and F3. Interestingly, devices that rely on the F1 + N-719 co-sensitization approach had greater photocurrent and photovoltage than the standard N-719 dye, generating a power conversion efficiency (PCE) of 9.97%. This improved performance was mostly due to a higher JSC value of 23.28 mA cm−2 for the dye F1 and a maximum molar extinction coefficient in the 350–550 nm region, which enhanced the light-harvesting capacity of the N-719 dye.

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References

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

    Article  CAS  Google Scholar 

  2. M. Gratzel, Solar energy conversion by dye-sensitized photovoltaic cells. Inorg. Chem. 44, 6841–6851 (2005)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  4. X. Meng, C. Yu, X. Zhang, L. Huang, M. Rager, J. Hong, J. Qiu, Z. Lin, Active site senriched carbon matrix enables efficient triiodide reduction in dye-sensitized solar cells: an understanding of the active centers. Nano Energy 54, 138–147 (2018)

    Article  CAS  Google Scholar 

  5. X. Meng, C. Yu, X. Song, J. Iocozzia, J. Hong, M. Rager, H. Jing, S. Wang, L. Huang, J. Qiu, Z. Lin, Scrutinizing defects and defect density of selenium-doped Graphene for high-efficiency triiodide reduction in dye-sensitized solar cells. Angew. Chem. Int. Ed. 130, 4772–4776 (2018)

    Article  Google Scholar 

  6. M. Barrera, I. Crivelli, B. Loeb, On the performance of ruthenium dyes in dye sensitized solar cells: a free cluster approach based on theoretical indexes. J. Mol. Model. 22, 118 (2016)

    Article  CAS  Google Scholar 

  7. S. Aghazada, M.K. Nazeeruddin, Ruthenium complexes as sensitizers in dye sensitized solar cells. Inorganics 6, 52 (2018)

    Article  CAS  Google Scholar 

  8. C. Woodward, T. Rüther, C. Coghlan, T. Jones, Y. Hebting, R. Cordiner, R. Dawson, D. Robinson, C. Forsyth, G. Wilson, Preparation of tetracarboxylated bis-bipyridine Ruthenium dyes: synthesis, structural and electronic characterization. Chem. Plus Chem. 83, 691–703 (2018)

    CAS  Google Scholar 

  9. A. Sen, A. Gro, β effect of electron withdrawing/donating groups on the sensitizing action of the novel organic dye “3-(5-(4-(Diphenylamino)Styryl)Thiophen-2-Yl)-2-Cyanoacrylic Acid” for N-Type dye sensitized solar cells: a theoretical study. J. Phys. Chem. C 124(16), 8526–8540 (2020)

    Article  CAS  Google Scholar 

  10. A. Mishra, M.K.R. Fischer, P. Büuerle, Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules. Angew. Chem. Int. Ed. 48(14), 2474–2499 (2009)

    Article  CAS  Google Scholar 

  11. S. Singh, M. Chandrasekharam, K. Gupta, A. Islam, L. Han, G. Sharma, Co-sensitization of amphiphilic ruthenium(II) sensitizer with a metal free organic dye: improved photovoltaic performance of dye sensitized solar cells. Org. Electron. 14, 1237–1241 (2013)

    Article  CAS  Google Scholar 

  12. J. Luo, Z. Wan, C. Jia, Y. Wang, X. Wu, A co-sensitized approach to efficiently fill the absorption valley, avoid dye aggregation and reduce the charge recombination. Electrochim. Acta 215, 506–514 (2016)

    Article  CAS  Google Scholar 

  13. Y.-J. Chen, Y.-C. Chang, L.-Y. Lin, W.-C. Chang, S.-M. Chang, Enhancing the spectral response of mesoporous ZnO films of dye–sensitized solar cells by incorporating metal-free organic sensitizer and N719 dye. Electrochim. Acta 178, 414–419 (2015)

    Article  CAS  Google Scholar 

  14. A. Mishra, M. 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  CAS  Google Scholar 

  15. Z. Ning, Y. Fu, H. Tian, Improvement of dye-sensitized solar cells: what we know and what we need to know. Energy Environ. Sci. 3, 1170–1181 (2010)

    Article  CAS  Google Scholar 

  16. M. Al-Eid, S. Limb, K. Park, B. Fitzpatrick, C. Han, K. Kwak, J. Hong, G. Cooke, Facile synthesis of metal-free organic dyes featuring a thienylethynyl spacer for dye sensitized solar cells. Dyes Pigm. 104, 197–203 (2014)

    Article  CAS  Google Scholar 

  17. R.Y.-Y. Lin, F.-L. Wu, C.-H. Chang, H.-H. Chou, T.-M. Chuang, T.-C. Chu et al., 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  CAS  Google Scholar 

  18. S. Fernandes, M. Castro, D. Ivanou, A. Mendes, M. Raposo, Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox photovoltaic properties. Coatings 12(1), 34 (2022)

    Article  CAS  Google Scholar 

  19. K. Kavya, P. Naik, A. Adhikari, Simple thiophene based organic dyes as active photosensitizers for DSSC application: from molecular design to structure property relationship. J. Nano-Electron. Phys. 12, 02039 (2020)

    Google Scholar 

  20. S. Rouhani, M. Hosseinnezhad, N. Sohrab, K. Gharanjig, A. Salem, Z. Ranjbar, Investigation of the effect of rGO/TiO2 on photovoltaic performance of DSSCs devices. Prog. Color. Color. Coat 15, 123–131 (2022)

    Google Scholar 

  21. L. Zhang, J. Cole, Anchoring groups for dye-sensitized solar cells. ACS Appl. Mater. Interfaces 7, 3427–3455 (2015)

    Article  CAS  Google Scholar 

  22. F. Ambrosio, N. Martsinovich, A. Troisi, Effect of the anchoring group on electron injection: theoretical study of phosphonated dyes for dye-sensitized solar cells. J. Phys. Chem. C 116, 2622–2629 (2012)

    Article  CAS  Google Scholar 

  23. B. Hosseinzadeh, A.S. Beni, A.N. Chermahini, R. Ghahary, A. Teimouri, Novel organic dyes with anchoring group of barbituric/thiobarbituric acid and their application in dye-sensitized solar cells. Synth. Met 209, 1–10 (2015)

    Article  CAS  Google Scholar 

  24. S. Badawy, R. Su, A. Fadda, E. Abdel-Latif, A. El-Shafei, M. Elmorsy, Highly efficient (N-benzothiazolyl)-cyanoacetamide based co-sensitizers for high efficiency dye-sensitized solar cells. Optik 249, 168274 (2022)

    Article  CAS  Google Scholar 

  25. K. Harmanda, K. Tavera, M. Gezgin, M. Nebioğlu, İ Şişman, G. Jirón, D. Atilla, A. Gürek, A new sterically hindered asymmetric zinc phthalocyanine as an efficient sensitizer for dye-sensitized solar cells. New J. Chem. 46, 714–725 (2022)

    Article  Google Scholar 

  26. M. Elmorsy, E. Abdel-Latif, S. Badawy, A. Fadda, New cyanoacetanilides based dyes as effective co-sensitizers for DSSCs sensitized with ruthenium (II) complex (HD-2). J. Mater. Sci. Mater. Electron. 31, 7981–7990 (2020)

    Article  CAS  Google Scholar 

  27. L. da Silva, M. Sánchez, M. Rodriguez, H. Freeman, Isomeric tetrazole-based organic dyes for dye-sensitized solar cells: structure-property relationships. J. Mol. Struct. 1250, 131749 (2022)

    Article  CAS  Google Scholar 

  28. M. Eltoukhi, A. Fadda, E. Abdel-Latif, M. Elmorsy, Low cost carbazole-based organic dye bearing the acrylamides and 2-pyridone moieties for efficient dye-sensitized solar cells. J. Photochem. Photobiol. A 426, 113760 (2022)

    Article  CAS  Google Scholar 

  29. S. Fernandes, M. Castro, L. Mesquita, L. Andrade, A. Mendes, M. Raposo, Synthesis and characterization of novel thieno [3, 2-b] thiophene based metal-free organic dyes with different heteroaromatic donor moieties as sensitizers for dye-sensitized solar cells. Dyes Pigm. 136, 46–53 (2017)

    Article  CAS  Google Scholar 

  30. D. Babu, R. Su, A. El-Shafei, A. Adhikari, From molecular design to cosensitization; High performance indole based photosensitizers for dye-sensitized solar cells. Electrochim. Acta 198, 10–21 (2016)

    Article  CAS  Google Scholar 

  31. M. Nazeeruddin, M. Zakeeruddin, R. Humphry-Baker, M. Jirousek, P. Liska, N. Vlachopoulos, M. Grätzel, Acid−Base equilibria of (2, 2 ‘-Bipyridyl-4, 4 ‘-dicarboxylic acid) ruthenium (II) complexes and the effect of protonation on charge-transfer sensitization of nanocrystalline titania. Inorg. Chem. 38, 6298–6305 (1999)

    Article  CAS  Google Scholar 

  32. Y. Shu, A. Mikosch, K.N. Winzenberg, P. Kemppinen, C.D. Easton, A. Bilic, C.M. Forsyth, C.J. Dunn, T.B. Singha, G.E. Collis, N-Alkyl functionalized barbituric and thiobarbituric acid bithiophene derivatives for vacuum deposited n-channel OFETs. J. Mater. Chem. C 2(20), 3895–3899 (2014)

    Article  CAS  Google Scholar 

  33. M.A. Ismail, M.H. Abdel-Rhman, G.A. Abdelwahab, W.S. Hamama, H.M. El-Shafeai, W.M. El-Sayed, Synthesis of new thienylpicolinamidine derivatives and possible mechanisms of antiproliferative activity. RSC Adv. 10, 41165–41176 (2020)

    Article  CAS  Google Scholar 

  34. M.S. McClure, F. Roschangar et al., A practical one-pot synthesis of 5-aryl-2-furaldehydes. Synthesis 11, 1681–1685 (2001)

    Article  Google Scholar 

  35. M.A. Ismail, D.W. Boykin, C.E. Stephens, An efficient synthesis of 5,5’-diaryl-2,2’-bichalcophenes. Tetrahedron Lett. 47, 795–797 (2006)

    Article  CAS  Google Scholar 

  36. A. Mishra, C. Ma, P. Bäuerle, Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications. Chem. Rev. 109, 1141–1276 (2009)

    Article  CAS  Google Scholar 

  37. Z. Iqbal, W.-Q. Wu, D.-B. Kuang, L. Wang, H. Meier, D. Cao, Phenothiazine-based dyes with bilateral extension of π-conjugation for efficient dye-sensitized solar cells. Dyes Pigm. 96, 722–731 (2013)

    Article  CAS  Google Scholar 

  38. J. Yang, P. Ganesan, J. Teuscher, T. Moehl, Y. Kim, C. Yi, P. Comte, K. Pei, T. Holcombe, M. Nazeeruddin, J. Hua, S. Zakeeruddin, H. Tian, M. Grätzel, Influence of the donor size in D-π-A organic dyes for dye-sensitized solar cells. J. Am. Chem. Soc. 136, 5722–5730 (2014)

    Article  CAS  Google Scholar 

  39. J. Luo, Z. Wan, C. Jia, Y. Wang, X. Wu, X. Yao, Co-sensitization of dithiafulvenyl-phenothiazine based organic dyes with N719 for efficient dye-sensitized solar cells. Electrochim. Acta 211, 364–374 (2016)

    Article  CAS  Google Scholar 

  40. H. Tian, X. Yang, J. Cong, R. Chen, C. Teng, J. Liu, Y. Hao, L. Wang, L. Sun, Effect of different electron donating groups on the performance of dye-sensitized solar cells. Dyes Pigm. 84, 62–68 (2010)

    Article  CAS  Google Scholar 

  41. Z.-S. Huang, H.-L. Feng, X.-F. Zang, Z. Iqbal, H. Zeng, D.-B. Kuang, L. Wang, H. Meier, D. Cao, Dithienopyrrolobenzothiadiazole-based organic dyes for efficient dye-sensitized solar cells. J. Mater. Chem. A 2, 15365–15376 (2014)

    Article  CAS  Google Scholar 

  42. J. Zhao, X. Yang, M. Cheng, S. Li, L. Sun, Molecular design and performance of hydroxylpyridium sensitizers for dye-sensitized solar cells. ACS. Appl. Mater. Interfaces 5, 5227–5231 (2013)

    Article  CAS  Google Scholar 

  43. M. Frisch, G.W. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, Eur. J. Inorg. Chem. 3690–3697 (2017), www.eurjic.org 3697 © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, W. C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009.

  44. J.N. Clifford, E. Martínez-Ferrero, A. Viterisi, E. Palomares, Sensitizer molecular structure-device efficiency relationship in dye sensitized solar cells. Chem. Soc. Rev. 40, 1635–1646 (2011)

    Article  CAS  Google Scholar 

  45. M. Rashid, D. Hayati, K. Kwak, J. Hong, Theoretical investigation of azobenzene-based photochromic dyes for dye-sensitized solar cells. Nanomaterials 10, 914 (2020)

    Article  CAS  Google Scholar 

  46. Y.-J. Chen, Y.-C. Chang, L.-Y. Lin, W.-C. Chang, S.-M. Chang, Enhancing the spectral response of mesoporous ZnO films of dye-sensitized solar cells by incorporating metal-free organic sensitizer and N719 dye. Electrochim. Acta 178, 414–419 (2015)

    Article  CAS  Google Scholar 

  47. N. Neale, N. Kopidakis, J. van de Lagemaat, M. Grätzel, A. Frank, Effect of a coadsorbent on the performance of dye-sensitized TiO2 solar cells: shielding versus band-edge movement. J. Phys. Chem. B 109, 23183–23189 (2005)

    Article  CAS  Google Scholar 

  48. M.R. Elmorsy, L. Lyu, E. Abdel-Latif, S. Badawy, A.M. El-Shafei, A. Fadda, Co-sensitization of HD-2 complex with low-cost cyanoacetanilides for highly efficient DSSCs. Photochem. Photobiol. Sci. 19, 281–288 (2020)

    Article  CAS  Google Scholar 

  49. P. Naik, R. Su, M.R. Elmorsy, A. El-Shafei, A.V. Adhikari, Investigation of new carbazole based metal-free dyes as active photosensitizers/co-sensitizers for DSSCs. Dyes Pigm. 149, 177–187 (2017)

    Article  CAS  Google Scholar 

  50. G. Oskam, B.V. Bergeron, G.J. Meyer, P.C. Searson, pseudohalogens for dye-sensitized TiO2 photoelectrochemical cells. J. Phys. Chem. B 105, 6867–6873 (2001)

    Article  CAS  Google Scholar 

  51. Y. Hua, B. Jin, H. Wang, X. Zhu, W. Wu, M.-S. Cheung, Z. Lin, W.-Y. Wong, W.-K. Wong, Bulky dendritic triarylamine-based organic dyes for efficient co-adsorbent-free dye-sensitized solar cells. J. Power Sources 237, 195–203 (2013)

    Article  CAS  Google Scholar 

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FHA: synthesis, methodology, and graphical plots. MAI and EA-L: supervision, initial corrections, and comments. AAA: optical proprieties measurements, data analysis and revision. MRE: writing original draft, data analysis, editing, proofreading, and manuscript handling. All the authors read and approved the final manuscript.

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Correspondence to Mohamed R. Elmorsy.

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Abdelhamed, F.H., Ismail, M.A., Abdel-Latif, E. et al. Design and synthesis of novel bichalcophene derivatives with double anchoring groups for dye-sensitized solar cell applications: sensitization and co-sensitization with N-719. J Mater Sci: Mater Electron 33, 15665–15678 (2022). https://doi.org/10.1007/s10854-022-08470-9

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