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The Performance Evaluation of Meso-Tetraphenyl Porphyrin and Azo Dyes as Photosensitizers in Dye-sensitized Solar Cells

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Abstract

The photovoltaic properties of five different mono-azo function and meso-tetraphenyl porphyrin dyes have been investigated by computational DFT/TDDFT calculations and measurement of the J-V properties of their cells. The photovoltaic efficiency of the cells based on these dyes were determined by both experimental and theoretical methods. The efficiency-to-cost ratios of the azo-dye cells showed that they could be cheaper substitutes to porphyrin-based cells. Eriochrome blue black (EBB) and eriochrome black T (EBT) cells were shown to possess the best photovoltaic properties by the two methods employed (theory and experiment). The presence of two naphthol moieties at both ends of their -N = N- group has been adduced as possible reason for their relatively outstanding performance. The extremely low efficiency-to-cost ratio obtained for cell-POR suggests that the use of porphyrin as sensitizer may not be as economically viable as some azo dyes. MTO, EBB and EBT were found to be the most cost-effective among the investigated dyes. The porphyrin’s low performance may have been amplified by the absence of an effective anchor group in its molecular structure.

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References

  1. Punch Newspaper (2023) : Grid collapses 98 times under Buhari amid N1.52tn bailout (punchng.com), accessed on Wednesday, 21st

  2. (a) United Nations Population Division. World Population Prospects (2022) Revision : (b) Census reports and other statistical publications from national statistical offices, (c) Eurostat: Demographic Statistics, (d) United Nations Statistical Division. Population and Vital Statistics Report (various years), (e) U.S. Census Bureau: International Database, and (f) Secretariat of the Pacific Community: Statistics and Demography Programme. Population, total - Nigeria | Data (worldbank.org), accessed on Tuesday, 20th June, 2023

  3. Aliyu AS, Ramli AT, Saleh MA (2013) Nigeria electricity crisis: power generation capacity expansion and environmental ramifications. Energy 61:354–367

    Article  Google Scholar 

  4. PwC’s Annual Power and Utilities (2023) Roundtable The challenges with transforming the Nigerian power landscape. Available at power-roundtable-2016.pdf (pwc.com), and accessed on Wednesday, 2nd

  5. Nigeria to improve electricity access and services to citizens (2023) Available at Nigeria to Improve Electricity Access and Services to Citizens (worldbank.org), and accessed on Wednesday, 2nd

  6. Nigeria carbon (CO2) (2023) emissions 1990–2023. Available at Nigeria Carbon (CO2) Emissions 1990–2023 | MacroTrends, and accessed on Wednesday, 2nd

  7. Power problems (2023) : could solar solve Nigeria’s electricity woes? Available at Power problems: Could solar solve Nigeria’s electricity woes? | Energy News | Al Jazeera, and accessed on Wednesday, 2nd

  8. Electricity production from (2023) renewable sources, excluding hydroelectric (kWh) – Nigeria. Available at Electricity production from renewable sources, excluding hydroelectric (kWh) - Nigeria | Data (worldbank.org), and accessed on Thursday, 3rd

  9. Tunç G, Zambrano-Angulo M, Arslan BS, Güzel E, Nebioğlu M, Ahsen V, Şişman ĺ, Cárdenas-Jirón G, Gürek AG (2021) Insight into the effects of the anchoring groups on the photovoltaic performance of unsymmetrical phthalocyanine based dye-sensitized solar cells. Dalton Trans 50:2981–2996

    Article  PubMed  Google Scholar 

  10. Zhu B-y, Wu L, Ye Q, Gao J-r, Han L (2017) Asymmetric double donor-π-acceptor dyes based on phenothiazine and carbazole donors for dye-sensitized solar cells. Tetrahedron Lett 73:6307–6315

    Article  CAS  Google Scholar 

  11. Ren Y, Zhang D, Suo J, Cao Y, Eickemeyer FT, Vlachopoulos N, Zakeeruddin SM, Hagfeldt A, Grätzel M (2023) Hydroxamic acid pre-adsorption raises the efficiency of cosensitized solar cells. Nature 613:60–65

    Article  ADS  CAS  PubMed  Google Scholar 

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

    Article  ADS  Google Scholar 

  13. Li L-L, Diau W-G (2013) Porphyrin-sensitized solar cells. Chem Soc Rev 42:291–304

    Article  CAS  PubMed  Google Scholar 

  14. Birel Ö, Nadeem S, Duman H (2017) Porphyrin-based dye-sensitized solar cells (DSSCs): a review. J Fluoresc 27:1075–1085

    Article  CAS  PubMed  Google Scholar 

  15. Mahmood A, Hu J-Y, Xiao B, Tang A, Wang X, Zhou E (2018) Recent progress in porphyrin-based materials for organic solar cells. J Mater Chem A 6:16769–16797

    Article  CAS  Google Scholar 

  16. Mathew S, Yella A, Gao P, Humphry-Baker R, Curchod BFE, Ashari-Astani N, Tavernelli I, Rothlisberger U, Nazeeruddin MK, Grätzel M (2014) Dye-sensitized solar cells with 13% efficiency achieved through the molecular engineering of porphyrin sensitizers. Nat Chem 6:242–247

    Article  CAS  PubMed  Google Scholar 

  17. Vaiano V, De Marco I (2023) Removal of azo dyes from wastewater through heterogeneous photocatalysis and supercritical water oxidation. Separations 10:230–254

    Article  CAS  Google Scholar 

  18. Patil R, Jadhav L, Borane N, Mishra S, Patil SV (2023) Industrial waste lignosulphonate to functionalized azo pigments: an application to epoxy-polyamine composite coating. Biomass Conv Bioref. https://doi.org/10.1007/s13399-023-04226-5

    Article  Google Scholar 

  19. Mahmood A, Tahir MH, Irfan A, Al-Sehemi AG, Al-Assiri MS (2015) Heterocyclic azo dyes for dye sensitized solar cells: a quantum chemical study. Comput Theor Chem 1066:94–99

    Article  CAS  Google Scholar 

  20. Mikroyannidis JA, Tsagkournos DV, Balraju P, Sharma GD (2011) Low band gap dyes based on 2-styryl-5-phenylazo-pyrrole: synthesis and application for efficient dye-sensitized solar cells. J Power Sources 196:4152–4161

    Article  CAS  Google Scholar 

  21. Yella A, Lee H-W, Tsao HN, Yi C, Chandiran AK, Nazeeruddin MK, Diau EW-G, Yeh C-Y, Zakeeruddin SM, Grätzel M (2011) Porphyrin-sensitized solar cells with cobalt (II/III)–based redox electrolyte exceed 12% efficiency. Science 334:629–633

    Article  ADS  CAS  PubMed  Google Scholar 

  22. The price of Eriochrome® (2023) Black T Available at Eriochrome Black T ACS reagent indicator grade 1787-61-7 (sigmaaldrich.com), and accessed on Sunday, 6th

  23. The price of (2023) Calcon (C.I.15705) available at Eriochrome blue-black r | Sigma-Aldrich (sigmaaldrich.com), and accessed on Sunday, 6th

  24. Alizarin Yellow R (2023) sodium salt, Thermo Scientific Chemicals. The price of Alizarin Yellow R sodium salt available at Alizarin Yellow R sodium salt, Thermo Scientific Chemicals | Fisher Scientific, and accessed on Sunday, 6th August

  25. The price of methyl orange available at Orange G (2023) – 1-Phenylazo-2-naphthol-6,8-disulfonic acid disodium salt (sigmaaldrich.com), and accessed on Sunday, 6th

  26. The price of methyl orange available at Methyl Orange for microscopy Hist (2023) indicator pH 3.0-4.4 547-58-0 (sigmaaldrich.com), and accessed on Sunday, 6th

  27. The price (2023) Of 5,10,15,20-Tetraphenyl-21H,23H-porphine available at 5,10,15,20-Tetraphenyl-21H,23H-porphine 97 917-23-7 (sigmaaldrich.com), and accessed on Sunday, 6th

  28. Ao G, Xiao Z, Qian X, Li Z, Wang Y, Zhang X, Song Y (2015) Nonlinear optical properties tuning in meso-tetraphenylporphyrin derivatives substituted with donor/acceptor groups in picosecond and nanosecond regimes. Molecules 20:5554–5565

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Sharma S, Nath M (2013) Synthesis of mesosubstituted dihydro-1,3-oxazinoporphyrins. Beilstein J Org Chem 9:496–502

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Seleim MM, Abu-Bakr MS, Hashem EY, El-Zohry AM (2009) Simultaneous determination of aluminum (III) and Iron (III) by first-derivative spectrophotometry in alloys. J Appl Spectrosc 76(4):554–563

    Article  ADS  CAS  Google Scholar 

  31. Victor RPD, Fontes LLM, Neves AA, de Queiroz MELR, de Oliveira AF, Miranda LDL (2019) Removal of orange G dye by manganese oxide nanostructures. J Braz Chem Soc 30:1769–1778

    CAS  Google Scholar 

  32. Young A, Sweet TR (1955) Complexes of eriochrome black T with calcium and magnesium. Anal Chem 27(3):418–420

    Article  CAS  Google Scholar 

  33. Al-kadhemy MFH, Saeed AA, Kadhum FJ, Mazloum SA, Aied HK (2014) The effect of (he – ne) laser irradiation on the optical properties of methyl orange doped PVA films. J Radiat Res Appl Sci 7:371–375

    Google Scholar 

  34. Ghanim D, Al-Kindi GY, Hassan AK (2020) Green synthesis of iron nanoparticles using black tea leaves extract as adsorbent for removing eriochrome blue-black B dye. Engin Tech J Part A 38(10):1558–1569

    Google Scholar 

  35. Fry HC, Liu Y, Dimitrijevic NM, Rajh T (2014) Photoinitiated charge separation in titanium dioxide metalloporphyrin peptide material. Nat Commun 5:4606

    Article  ADS  CAS  PubMed  Google Scholar 

  36. Chilukuri B, Mazur U, Hipps KW (2020) Structure, properties, and reactivity of porphyrins on surfaces and nanostructures with periodic DFT calculations. Appl Sci 10:740, 1–26

    Article  Google Scholar 

  37. Karmakar A, Singh B (2017) Charge-transfer complex of 1-(2-thiazolylazo)-2-naphthol with aromatic nitro compounds: experimental and theoretical studies. J Mol Liq 247:425–433

    Article  CAS  Google Scholar 

  38. Zhang X-F, Li X, Niu L, Sun L, Liu L (2009) Charge transfer photophysics of tetra(α-amino) zinc phthalocyanine. J Fluoresc 19:947–954

    Article  PubMed  Google Scholar 

  39. Omura T, Kayane Y, Tezuka Y (1992) Design of chlorine-fast reactive dyes. Part 1: the role of sulphonate groups and optimization of their positions in an Arylazonaphthol system. Dyes Pigm 20:227–246

    Article  CAS  Google Scholar 

  40. Li L-L, Diau EW-G (2013) Porphyrin-sensitized solar cells. Chem Soc Rev 42:291–304

    Article  CAS  PubMed  Google Scholar 

  41. Mahmood A, Hu J-Y, Xiao B, Tang A, Wang X, Zhou E (2018) Recent progress of porphyrin-based materials for organic solar cells. J Mater Chem A 6:16769–16797

    Article  CAS  Google Scholar 

  42. Sanusi K, Atewolara-Odule OC, Sanyaolu NO, Ibikunle AA, Khoza BP, Fatomi NO, Fasanya SA, Abuka HE, Jesugbile EO, Yilmaz Y, Ceylan Ü (2023) Effects of solvents and substituents on the adsorptive and photovoltaic properties of porphyrins for dye-sensitized solar cell application: a theoretical consideration. Struct Chem 34:891–904

    Article  CAS  Google Scholar 

  43. Sanusi K, Fatomi NO, Borisade AO, Yilmaz Y, Ceylan Ü, Fashina A (2019) An approximate procedure for profiling dye molecules with potentials as sensitizers in solar cell application: a DFT/TD-DFT approach. Chem Phys Lett 723:111–117

    Article  ADS  CAS  Google Scholar 

  44. Halim SA, Ibrahim MA (2022) Synthesis, structure investigation, DFT analysis, optical, and photoelectrical properties of 9-bromo-3-hydroxychromeno[4,3-b]pyrazolo[4,3-e]pyridin-5(1H)-one (BHCPP). Results Chem 4:100572, 1–16

    Google Scholar 

  45. Sanusi K, Amuhaya EK, Nyokong T (2014) Enhanced optical limiting behavior of an indium-phthalocyanine single-walled carbon nanotube composite: an investigation of the effects of solvents. J Phys Chem C 118:7057–7069

    Article  CAS  Google Scholar 

  46. Yang H, Han C, Zhu X, Liu Y, Zhang KY, Liu S, Zhao Q, Li F, Huang W (2016) Upconversion luminescent chemodosimeter based on NIR organic dye for monitoring methylmercury in vivo. Adv Funct Mater 26:1945–1953

    Article  CAS  Google Scholar 

  47. Aderne R, Strassel K, Jenatsch S, Diethelm M, Hany R, Nüesch F, Carvalho RdosS, Legnani C, Cremona M (2019) Near-infrared absorbing cyanine dyes for all-organic optical upconversion devices. Org Electr 74:96–102

    Article  CAS  Google Scholar 

  48. Gonsalves AM, d’A. Rocha; Verajão MTB, Jorge; Pereira MM (1991) Some new aspects related to the synthesis of meso-substituted porphyrins. J Heterocycl Chem 28:635–640

    Article  CAS  Google Scholar 

  49. Tran-Thi TH, Lipskier JF, Maillard P, Momenteau M, Lopez-Castillo JM, Jay-Gerin JP (1992) Effect of the exciton coupling on the optical and photophysical properties of face-to-face porphyrin dimer and trimer. A treatment including the solvent stabilization effect. J Phys Chem 96(1992):1073–1082

    Article  CAS  Google Scholar 

  50. High JS, Virgil KA, Jakubikova E (2015) Electronic structure and absorption properties of strongly coupled porphyrin-perylene arrays. J Phys Chem A 119:9879–9888

    Article  CAS  PubMed  Google Scholar 

  51. Kubheka G, Sanusi K, Mack J, Nyokong T (2018) Optical limiting properties of 3,5-dipyrenylvinyleneBODIPY dyes. Spectrochim Acta Part A: Mol Biomol Spec 191:357–364

    Article  ADS  CAS  Google Scholar 

  52. Takano Y, Houk KN (2005) Benchmarking the conductor-like polarizable continuum model (CPCM) for aqueous solvation free energies of neutral and ionic organic molecules. J Chem Theory Comput 1:70–77

    Article  PubMed  Google Scholar 

  53. Yilmaz Y, Ozdemir M, Sanusi K, Fatomi NO, Khoza PB (2022) Aggregation effect on phthalocyanine photocatalytic degradation efficiency using orange G and methyl orange as test-pollutant compounds in aqueous medium. ChemSelect, 7, e202202958, 1–10

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Acknowledgements

The authors, in particular KS, NOF and PBK, are grateful to the management of the Centre for High Performance Computing (CHPC), South Africa, for giving us access to their central supercomputing cluster.

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A.O.O., N.O.S., A.A.I., S.T.Y., S.A.O. and O.C.A. were involved in the synthesis of the porphyrin, purification and characterization, and provided the azo dyes. A.O.O. and K.S. prepared the solar cells. A.O.O., N.O.S., A.A.I., S.T.Y., S.A.O., N.O.F. and O.C.A. carried out the I-V characteristics experiments on the solar cells. N.O.F. and P.B.K. performed the DFT calculations. K.S. and P.B.K analyzed the DFT results. K.S., N.O.S., A.A.I., S.T.Y., S.A.O. and O.C.A. performed the I-V data analysis. K.S. prepared the figures and Tables and wrote the main manuscript. All authors reviewed the manuscript.

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Correspondence to Kayode Sanusi.

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Sanusi, K., Olukoya, A.O., Sanyaolu, N.O. et al. The Performance Evaluation of Meso-Tetraphenyl Porphyrin and Azo Dyes as Photosensitizers in Dye-sensitized Solar Cells. J Fluoresc (2024). https://doi.org/10.1007/s10895-024-03632-w

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