Skip to main content
Log in

A carboxylate group modified the electrochemistry and photovoltaic properties of vanillin-substituted zinc porphyrin dye

  • Original Paper
  • Published:
Journal of Solid State Electrochemistry Aims and scope Submit manuscript

Abstract

A straightforward condensation method has been employed to introduce the potential alternative anchoring group of vanillin in porphyrins. Depending on the number of carboxylate groups in the porphyrin ring, the electrochemical and optical properties were studied. A slight hypsochromic shift was observed when the number of carboxylate groups in porphyrins increased in the emission and absorption bands. Calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels from cyclic and differential pulsed voltammogram studies clearly indicate that the LUMO energy levels of the dyes vary significantly with the number of carboxylate groups. It improves the electron injection dynamics of porphyrin-sensitized solar cell devices, offering them to achieve 0.36% PCE in PC-3 dye. Additionally, the recombination kinetics, denoted by τrec and krec, which are also affected by the carboxylate group, was calculated using the transient photovoltage decay. This demonstrates that the process of recombination at vanillin-anchored porphyrin dyes with carboxylate groups occurs very slowly.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15

Similar content being viewed by others

References

  1. Marszal AJ, Heiselberg P, Bourrelle JS (2011) Zero energy building–a review of definitions and calculation methodologies. Energy Build 43:971–979

    Article  Google Scholar 

  2. Fagiolari L, Sampò M, Lamberti A (2022) Integrated energy conversion and storage devices: interfacing solar cells, batteries and supercapacitors. Energy Storage Mater

  3. Bandara TMWJ, Hansadi JMC, Bella F (2022) A review of textile dye-sensitized solar cells for wearable electronics. Ionics 28:2563–2583

    Article  CAS  Google Scholar 

  4. Liu X, Fang J, Liu Y, Lin T (2016) Progress in nanostructured photoanodes for dye-sensitized solar cells. Front Mater Sci 10:225–237

    Article  Google Scholar 

  5. Richhariya G, Kumar A, Shukla AK (2023) Effect of different counter electrodes on power conversion efficiency of DSSCs. J Electron Mater 52:60–71

    Article  CAS  Google Scholar 

  6. Ruba N, Prakash P, Sowmya S (2021) Recent advancement in photo-anode, dye and counter cathode in dye-sensitized solar cell: a review. J Inorg Organomet Polym Mater 31:1894–1901

    Article  CAS  Google Scholar 

  7. Ahmed U, Alizadeh M, Abd Rahim N (2018) A comprehensive review on counter electrodes for dye sensitized solar cells: a special focus on Pt-TCO free counter electrodes. Sol Energy 174:1097–1125

    Article  CAS  Google Scholar 

  8. Lavagna L, Syrrokostas G, Fagiolari L (2021) Platinum-free photoelectrochromic devices working with copper-based electrolytes for ultrastable smart windows. J Mater Chem A 9:19687–19691

    Article  CAS  Google Scholar 

  9. Azarian MH, Wootthikanokkhan J (2020) Gelatin-based solid electrolytes for chromogenic windows applications: a review. Ionics 26:5841–5851

    Article  CAS  Google Scholar 

  10. Wang N, Hu J, Gao L, Ma T (2020) Current progress in solid-state electrolytes for dye-sensitized solar cells: a mini-review. J Electron Mater 49:7085–7097

    Article  Google Scholar 

  11. Devadiga D, Selvakumar M, Shetty P, Santosh MS (2021) Dye-sensitized solar cell for indoor applications: a mini-review. J Electron Mater 50:3187–3206

    Article  CAS  Google Scholar 

  12. 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 

  13. Wang X-F, Wang L, Tamai N (2011) Development of solar cells based on synthetic near-infrared absorbing purpurins: observation of multiple electron injection pathways at cyclic tetrapyrrole–semiconductor interface. J Phys Chem C 115:24394–24402

    Article  CAS  Google Scholar 

  14. Wang X-F, Tamiaki H (2010) Cyclic tetrapyrrole based molecules for dye-sensitized solar cells. Energy Environ Sci 3:94–106

    Article  CAS  Google Scholar 

  15. Urbani M, Ragoussi M-E, Nazeeruddin MK, Torres T (2019) Phthalocyanines for dye-sensitized solar cells. Coord Chem Rev 381:1–64

    Article  CAS  Google Scholar 

  16. Ragoussi M-E, Ince M, Torres T (2013) Recent advances in phthalocyanine-based sensitizers for dye-sensitized solar cells. Eur J Org Chem 2013:6475–6489

    Article  CAS  Google Scholar 

  17. Wang X-F, Kitao O (2012) Natural chlorophyll-related porphyrins and chlorins for dye-sensitized solar cells. Molecules 17:4484–4497

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  20. Mathew S, Yella A, Gao P (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 

  21. Xie M, Bai F-Q, Wang J (2018) Theoretical investigations on the unsymmetrical effect of β-link Zn–porphyrin sensitizers on the performance for dye-sensitized solar cells. Phys Chem Chem Phys 20:3741–3751

    Article  CAS  PubMed  Google Scholar 

  22. Kumar PR, Britto NJ, Kathiravan A (2019) Synthesis and electronic properties of A 3 B-thienyl porphyrins: experimental and computational investigations. New J Chem 43:1569–1580

    Article  CAS  Google Scholar 

  23. Kumar PR, Shajan XS, Mothi EM (2020) Pyridyl/hydroxyphenyl versus carboxyphenyl anchoring moieties in Zn–thienyl porphyrins for dye sensitized solar cells. Spectrochim Acta Part A Mol Biomol Spectrosc 224:117408

    Article  CAS  Google Scholar 

  24. Zhu Y, Silverman RB (2007) Electronic effects of peripheral substituents at porphyrin meso positions. J Org Chem 72:233–239

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Lopes JMS, Reis JRT, Machado AEH (2020) Influence of the meso-substituents on the spectral features of free-base porphyrin. Spectrochim Acta Part A Mol Biomol Spectrosc 238:118389

    Article  CAS  Google Scholar 

  26. O’regan B, Grätzel M (1991) A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. nature 353:737

  27. Ishida M, Park SW, Hwang D (2011) Donor-substituted β-functionalized porphyrin dyes on hierarchically structured mesoporous TiO2 spheres. Highly efficient dye-sensitized solar cells. The Journal of Physical Chemistry C 115:19343–19354

    Article  CAS  Google Scholar 

  28. Gorduk S, Altindal A (2020) Non-peripherally tetra substituted phthalocyanines bearing carboxylic acid anchoring groups as photosensitizer for high efficient dye-sensitized solar cells. J Mol Struct 1204:127636

    Article  CAS  Google Scholar 

  29. Baktash A, Khoshnevisan B, Sasani A, Mirabbaszadeh K (2016) Effects of carboxylic acid and phosphonic acid anchoring groups on the efficiency of dye sensitized solar cells: a computational study. Org Electron 33:207–212

    Article  CAS  Google Scholar 

  30. Chen C, Yang X, Cheng M (2013) Degradation of cyanoacrylic acid-based organic sensitizers in dye-sensitized solar cells. Chemsuschem 6:1270–1275

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  32. Odobel F, Blart E, Lagrée M (2003) Porphyrin dyes for TiO 2 sensitization. J Mater Chem 13:502–510

    Article  CAS  Google Scholar 

  33. He H, Gurung A, Si L (2012) 8-Hydroxylquinoline as a strong alternative anchoring group for porphyrin-sensitized solar cells. Chem Commun 48:5910–5912

    Article  CAS  Google Scholar 

  34. Ma T, Inoue K, Noma H (2002) Effect of functional group on photochemical properties and photosensitization of TiO2 electrode sensitized by porphyrin derivatives. J Photochem Photobiol, A 152:207–212

    Article  CAS  Google Scholar 

  35. Faliang G, Xu J, Ran F (2014) Strategy to improve photovoltaic performance of DSSC sensitized by zinc prophyrin using salicylic acid as a tridentate anchoring group

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

    Article  CAS  PubMed  Google Scholar 

  37. Li S-F, Yang X-C, Cheng M (2012) Novel D–π–A type II organic sensitizers for dye sensitized solar cells. Tetrahedron Lett 53:3425–3428

    Article  CAS  Google Scholar 

  38. Duan L, Uddin A (2020) Progress in stability of organic solar cells. Advanced Science 7:1903259

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Lo C-F, Hsu S-J, Wang C-L (2010) Tuning spectral and electrochemical properties of porphyrin-sensitized solar cells. The Journal of Physical Chemistry C 114:12018–12023

    Article  CAS  Google Scholar 

  40. Giribabu L, Kumar CV, Reddy PY (2006) Porphyrin-rhodanine dyads for dye sensitized solar cells. J Porphyrins Phthalocyanines 10:1007–1016

    Article  CAS  Google Scholar 

  41. Ram Kumar P, Mothi EM, Ramesh M, Kathiravan A (2018) Zn-Porphyrin propped with hydantoin anchor: synthesis, photophysics and electron injection/recombination dynamics. Phys Chem Chem Phys 20:5117–5127

    Article  CAS  PubMed  Google Scholar 

  42. Safar Sajadi SM, Khoee S (2021) The simultaneous role of porphyrins’ H- and J- aggregates and host–guest chemistry on the fabrication of reversible Dextran-PMMA polymersome. Sci Rep 11:2832

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. Andrade SM, Teixeira R, Costa SMB, Sobral AJFN (2008) Self-aggregation of free base porphyrins in aqueous solution and in DMPC vesicles. Biophys Chem 133:1–10

    Article  CAS  PubMed  Google Scholar 

  44. Alwin S, Shajan XS, Karuppasamy K, Warrier KGK (2017) Microwave assisted synthesis of high surface area TiO2 aerogels: a competent photoanode material for quasi-solid dye-sensitized solar cells. Mater Chem Phys 196:37–44

    Article  CAS  Google Scholar 

  45. Ramasubbu V, Kumar PR, Mothi EM (2019) Highly interconnected porous TiO2-Ni-MOF composite aerogel photoanodes for high power conversion efficiency in quasi-solid dye-sensitized solar cells. Appl Surf Sci 496:143646

    Article  CAS  Google Scholar 

Download references

Acknowledgements

PRK thanks PSN CET for providing the opportunity for spectroscopic measurements, PSSC cell fabrication, and studies. PRK expressed gratitude to SAIF at Cochin University in Kerala for providing the NMR characterization services.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ram Kumar P.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1313 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ram Kumar P A carboxylate group modified the electrochemistry and photovoltaic properties of vanillin-substituted zinc porphyrin dye. J Solid State Electrochem 27, 2545–2560 (2023). https://doi.org/10.1007/s10008-023-05531-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10008-023-05531-9

Keywords

Navigation