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Investigating the Effects of Fluorine Substituents on Organic Dyes in Dye-Sensitized Solar Cells

Year 2024, Volume: 11 Issue: 1, 1 - 10, 04.02.2024
https://doi.org/10.18596/jotcsa.1355244

Abstract

We synthesized and evaluated five organic dyes that featured both mono- and di-substituted fluorine atoms for application in dye-sensitized solar cells (DSSCs). The dye structure was designed with N, N-dimethylaniline as a donor, fluorophenyl as an π-conjugated bridge, and cyanoacetic acid as an anchoring and acceptor group. The fluorine substituents are strong electron-withdrawing groups, introducing different numbers and positions of fluorine atoms (ortho and meta) that were expected to the ability of the acceptor parts of the dye. The results showed that adding the fluorine mono-substitution in the ortho position can enhance the efficiency of the solar cells in comparison with the meta-substitution and unsubstituted one. However, the di-substitution by fluorine atoms in two ortho positions and ortho, meta positions reduced the performance of the solar cells. The reason was related to the effect of π-conjugation between the fluorine substituent and the carbonyl group of the carboxylic acid. The DSSCs based on dye 14 achieved the best results with power conversion efficiency (PCE) = 3.33%, (Jsc = 5.43 mA cm-2, Voc = 0.81V and FF = 75.85%) under standard conditions with I3-/I- as the electrolyte.

References

  • 1. Sharma S, Jain KK, Sharma A. Solar Cells: In Research and Applications—A Review. Mater Sci Appl [Internet]. 2015 Dec 1;06(12):1145–55. Available from: <URL>.
  • 2. Abdulrazzaq OA, Saini V, Bourdo S, Dervishi E, Biris AS. Organic Solar Cells: A Review of Materials, Limitations, and Possibilities for Improvement. Part Sci Technol [Internet]. 2013 Sep 3;31(5):427–42. Available from: <URL>.
  • 3. Ajayan J, Nirmal D, Mohankumar P, Saravanan M, Jagadesh M, Arivazhagan L. A review of photovoltaic performance of organic/inorganic solar cells for future renewable and sustainable energy technologies. Superlattices Microstruct [Internet]. 2020 Jul 1;143:106549. Available from: <URL>.
  • 4. Day J, Senthilarasu S, Mallick TK. Improving spectral modification for applications in solar cells: A review. Renew Energy [Internet]. 2019 Mar 1 [cited 2023 Oct 24];132:186–205. Available from: <URL>.
  • 5. Abdulhussein SF, Abdalhadi SM, Hanoon HD. Synthesis of new imidazole derivatives dyes and application in dye sensitized solar cells supported by DFT. Egypt J Chem [Internet]. 2022 Feb 5;65(9):211–7. Available from: <URL>.
  • 6. Abdalhadi SM, Al-Baitai AY, Al-Zubaidi HA. Synthesis and Characterization of 2,3-Diaminomaleonitrile Derivatives by One-Pot Schiff Base Reaction and Their Application in Dye Synthesized Solar Cells. Indones J Chem [Internet]. 2020 Dec 22;21(2):443. Available from: <URL>.
  • 7. Cariello M, Abdalhadi SM, Yadav P, Decoppet J-D, Zakeeruddin SM, Grätzel M, et al. An investigation of the roles furan versus thiophene π-bridges play in donor–π-acceptor porphyrin based DSSCs. Dalt Trans [Internet]. 2018;47(18):6549–56. Available from: <URL>.
  • 8. Abdalhadi SM, Connell A, Zhang X, Wiles AA, Davies ML, Holliman PJ, et al. Convenient synthesis of EDOT-based dyes by CH-activation and their application as dyes in dye-sensitized solar cells. J Mater Chem A [Internet]. 2016;4(40):15655–61. Available from: <URL>.
  • 9. Gong J, Sumathy K, Qiao Q, Zhou Z. Review on dye-sensitized solar cells (DSSCs): Advanced techniques and research trends. Renew Sustain Energy Rev [Internet]. 2017 Feb;68:234–46. Available from: <URL>.
  • 10. O’Regan B, Grätzel M. A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature [Internet]. 1991 Oct;353(6346):737–40. Available from: <URL>.
  • 11. Kakiage K, Aoyama Y, Yano T, Oya K, Fujisawa J, Hanaya M. Highly-efficient dye-sensitized solar cells with collaborative sensitization by silyl-anchor and carboxy-anchor dyes. Chem Commun [Internet]. 2015;51(88):15894–7. Available from: <URL>.
  • 12. Devadiga D, Selvakumar M, Shetty P, Santosh MS. Dye-Sensitized Solar Cell for Indoor Applications: A Mini-Review. J Electron Mater [Internet]. 2021 Jun 1;50(6):3187–206. Available from: <URL>.
  • 13. Mohammed N, Shakkor SJ, Abdalhadi SM, Al-Bayati YK. Two multifunctional benzoquinone derivatives as small molecule organic semiconductors for bulk heterojunction and perovskite solar cells. Main Gr Chem [Internet]. 2022 Dec 20;21(4):943–52. Available from: <URL>.
  • 14. Sharma K, Sharma V, Sharma SS. Dye-Sensitized Solar Cells: Fundamentals and Current Status. Nanoscale Res Lett [Internet]. 2018 Dec 28;13(1):381. Available from: <URL>.
  • 15. Talodthaisong C, Wongkhan K, Sudyoadsuk T, Saengsuwan S, Jitchati R. Comparison of the DSSC Efficiency on Synthetic N3 Dyes. Adv Mater Res [Internet]. 2015 Dec;1131:165–8. Available from: <URL>.
  • 16. Portillo-Cortez K, Martínez A, Dutt A, Santana G. N719 Derivatives for Application in a Dye-Sensitized Solar Cell (DSSC): A Theoretical Study. J Phys Chem A [Internet]. 2019 Dec 26;123(51):10930–9. Available from: <URL>.
  • 17. Liu S, Liu J, Wang T, Wang C, Ge Z, Liu J, et al. Preparation and photovoltaic properties of dye-sensitized solar cells based on zinc titanium mixed metal oxides. Colloids Surfaces A Physicochem Eng Asp [Internet]. 2019 May;568:59–65. Available from: <URL>.
  • 18. Numata Y, Islam A, Chen H, Han L. Aggregation-free branch-type organic dye with a twisted molecular architecture for dye-sensitized solar cells. Energy Environ Sci [Internet]. 2012;5(9):8548–52. Available from: <URL>.
  • 19. Ahmad S, Guillén E, Kavan L, Grätzel M, Nazeeruddin MK. Metal free sensitizer and catalyst for dye sensitized solar cells. Energy Environ Sci [Internet]. 2013;6(12):3439–66. Available from: <URL>.
  • 20. Sarrato J, Pinto AL, Malta G, Röck EG, Pina J, Lima JC, et al. New 3-Ethynylaryl Coumarin-Based Dyes for DSSC Applications: Synthesis, Spectroscopic Properties, and Theoretical Calculations. Molecules [Internet]. 2021 May 14;26(10):2934. Available from: <URL>.
  • 21. Al-horaibi SA, Asiri AM, El-Shishtawy RM, Gaikwad ST, Rajbhoj AS. Indoline and benzothiazole-based squaraine dye-sensitized solar cells containing bis-pendent sulfonate groups: Synthesis, characterization and solar cell performance. J Mol Struct [Internet]. 2019 Nov;1195:591–7. Available from: <URL>.
  • 22. Pati PB, Yang W, Zade SS. New dyes for DSSC containing triphenylamine based extended donor: Synthesis, photophysical properties and device performance. Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2017 May;178:106–13. Available from: <URL>.
  • 23. Lee C-P, Lin RY-Y, Lin L-Y, Li C-T, Chu T-C, Sun S-S, et al. Recent progress in organic sensitizers for dye-sensitized solar cells. RSC Adv [Internet]. 2015;5(30):23810–25. Available from: <URL>.
  • 24. Chang YJ, Chow TJ. Highly efficient triarylene conjugated dyes for sensitized solar cells. J Mater Chem [Internet]. 2011;21(26):9523–31. Available from: <URL>.
  • 25. Chen D-Y, Hsu Y-Y, Hsu H-C, Chen B-S, Lee Y-T, Fu H, et al. Organic dyes with remarkably high absorptivity; all solid-state dye sensitized solar cell and role of fluorine substitution. Chem Commun [Internet]. 2010;46(29):5256–8. Available from: <URL>.
  • 26. Chen B-S, Chen D-Y, Chen C-L, Hsu C-W, Hsu H-C, Wu K-L, et al. Donor–acceptor dyes with fluorine substituted phenylene spacer for dye-sensitized solar cells. J Mater Chem [Internet]. 2011;21(6):1937–45. Available from: <URL>.
  • 27. Wang Z-S, Cui Y, Dan-oh Y, Kasada C, Shinpo A, Hara K. Thiophene-Functionalized Coumarin Dye for Efficient Dye-Sensitized Solar Cells:  Electron Lifetime Improved by Coadsorption of Deoxycholic Acid. J Phys Chem C [Internet]. 2007 May 1;111(19):7224–30. Available from: <URL>.
  • 28. Yang H-Y, Yen Y-S, Hsu Y-C, Chou H-H, Lin JT. Organic Dyes Incorporating the Dithieno[3,2- b :2′,3′- d ]thiophene Moiety for Efficient Dye-Sensitized Solar Cells. Org Lett [Internet]. 2010 Jan 1;12(1):16–9. Available from: <URL>.
  • 29. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 16 Rev. C. 01, Wallingford, CT. Wallingford, CT. 2016;
  • 30. Chen X, Jia C, Wan Z, Yao X. Organic dyes with imidazole derivatives as auxiliary donors for dye-sensitized solar cells: Experimental and theoretical investigation. Dye Pigment [Internet]. 2014 May;104:48–56. Available from: <URL>.
  • 31. Aulakh RK, Sandhu S, Tanvi, Kumar S, Mahajan A, Bedi RK, et al. Designing and synthesis of imidazole based hole transporting material for solid state dye sensitized solar cells. Synth Met [Internet]. 2015 Jul;205:92–7. Available from: <URL>.
  • 32. Duvva N, Eom YK, Reddy G, Schanze KS, Giribabu L. Bulky Phenanthroimidazole–Phenothiazine D−π–A Based Organic Sensitizers for Application in Efficient Dye-Sensitized Solar Cells. ACS Appl Energy Mater [Internet]. 2020 Jul 27;3(7):6758–67. Available from: <URL>.
Year 2024, Volume: 11 Issue: 1, 1 - 10, 04.02.2024
https://doi.org/10.18596/jotcsa.1355244

Abstract

References

  • 1. Sharma S, Jain KK, Sharma A. Solar Cells: In Research and Applications—A Review. Mater Sci Appl [Internet]. 2015 Dec 1;06(12):1145–55. Available from: <URL>.
  • 2. Abdulrazzaq OA, Saini V, Bourdo S, Dervishi E, Biris AS. Organic Solar Cells: A Review of Materials, Limitations, and Possibilities for Improvement. Part Sci Technol [Internet]. 2013 Sep 3;31(5):427–42. Available from: <URL>.
  • 3. Ajayan J, Nirmal D, Mohankumar P, Saravanan M, Jagadesh M, Arivazhagan L. A review of photovoltaic performance of organic/inorganic solar cells for future renewable and sustainable energy technologies. Superlattices Microstruct [Internet]. 2020 Jul 1;143:106549. Available from: <URL>.
  • 4. Day J, Senthilarasu S, Mallick TK. Improving spectral modification for applications in solar cells: A review. Renew Energy [Internet]. 2019 Mar 1 [cited 2023 Oct 24];132:186–205. Available from: <URL>.
  • 5. Abdulhussein SF, Abdalhadi SM, Hanoon HD. Synthesis of new imidazole derivatives dyes and application in dye sensitized solar cells supported by DFT. Egypt J Chem [Internet]. 2022 Feb 5;65(9):211–7. Available from: <URL>.
  • 6. Abdalhadi SM, Al-Baitai AY, Al-Zubaidi HA. Synthesis and Characterization of 2,3-Diaminomaleonitrile Derivatives by One-Pot Schiff Base Reaction and Their Application in Dye Synthesized Solar Cells. Indones J Chem [Internet]. 2020 Dec 22;21(2):443. Available from: <URL>.
  • 7. Cariello M, Abdalhadi SM, Yadav P, Decoppet J-D, Zakeeruddin SM, Grätzel M, et al. An investigation of the roles furan versus thiophene π-bridges play in donor–π-acceptor porphyrin based DSSCs. Dalt Trans [Internet]. 2018;47(18):6549–56. Available from: <URL>.
  • 8. Abdalhadi SM, Connell A, Zhang X, Wiles AA, Davies ML, Holliman PJ, et al. Convenient synthesis of EDOT-based dyes by CH-activation and their application as dyes in dye-sensitized solar cells. J Mater Chem A [Internet]. 2016;4(40):15655–61. Available from: <URL>.
  • 9. Gong J, Sumathy K, Qiao Q, Zhou Z. Review on dye-sensitized solar cells (DSSCs): Advanced techniques and research trends. Renew Sustain Energy Rev [Internet]. 2017 Feb;68:234–46. Available from: <URL>.
  • 10. O’Regan B, Grätzel M. A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature [Internet]. 1991 Oct;353(6346):737–40. Available from: <URL>.
  • 11. Kakiage K, Aoyama Y, Yano T, Oya K, Fujisawa J, Hanaya M. Highly-efficient dye-sensitized solar cells with collaborative sensitization by silyl-anchor and carboxy-anchor dyes. Chem Commun [Internet]. 2015;51(88):15894–7. Available from: <URL>.
  • 12. Devadiga D, Selvakumar M, Shetty P, Santosh MS. Dye-Sensitized Solar Cell for Indoor Applications: A Mini-Review. J Electron Mater [Internet]. 2021 Jun 1;50(6):3187–206. Available from: <URL>.
  • 13. Mohammed N, Shakkor SJ, Abdalhadi SM, Al-Bayati YK. Two multifunctional benzoquinone derivatives as small molecule organic semiconductors for bulk heterojunction and perovskite solar cells. Main Gr Chem [Internet]. 2022 Dec 20;21(4):943–52. Available from: <URL>.
  • 14. Sharma K, Sharma V, Sharma SS. Dye-Sensitized Solar Cells: Fundamentals and Current Status. Nanoscale Res Lett [Internet]. 2018 Dec 28;13(1):381. Available from: <URL>.
  • 15. Talodthaisong C, Wongkhan K, Sudyoadsuk T, Saengsuwan S, Jitchati R. Comparison of the DSSC Efficiency on Synthetic N3 Dyes. Adv Mater Res [Internet]. 2015 Dec;1131:165–8. Available from: <URL>.
  • 16. Portillo-Cortez K, Martínez A, Dutt A, Santana G. N719 Derivatives for Application in a Dye-Sensitized Solar Cell (DSSC): A Theoretical Study. J Phys Chem A [Internet]. 2019 Dec 26;123(51):10930–9. Available from: <URL>.
  • 17. Liu S, Liu J, Wang T, Wang C, Ge Z, Liu J, et al. Preparation and photovoltaic properties of dye-sensitized solar cells based on zinc titanium mixed metal oxides. Colloids Surfaces A Physicochem Eng Asp [Internet]. 2019 May;568:59–65. Available from: <URL>.
  • 18. Numata Y, Islam A, Chen H, Han L. Aggregation-free branch-type organic dye with a twisted molecular architecture for dye-sensitized solar cells. Energy Environ Sci [Internet]. 2012;5(9):8548–52. Available from: <URL>.
  • 19. Ahmad S, Guillén E, Kavan L, Grätzel M, Nazeeruddin MK. Metal free sensitizer and catalyst for dye sensitized solar cells. Energy Environ Sci [Internet]. 2013;6(12):3439–66. Available from: <URL>.
  • 20. Sarrato J, Pinto AL, Malta G, Röck EG, Pina J, Lima JC, et al. New 3-Ethynylaryl Coumarin-Based Dyes for DSSC Applications: Synthesis, Spectroscopic Properties, and Theoretical Calculations. Molecules [Internet]. 2021 May 14;26(10):2934. Available from: <URL>.
  • 21. Al-horaibi SA, Asiri AM, El-Shishtawy RM, Gaikwad ST, Rajbhoj AS. Indoline and benzothiazole-based squaraine dye-sensitized solar cells containing bis-pendent sulfonate groups: Synthesis, characterization and solar cell performance. J Mol Struct [Internet]. 2019 Nov;1195:591–7. Available from: <URL>.
  • 22. Pati PB, Yang W, Zade SS. New dyes for DSSC containing triphenylamine based extended donor: Synthesis, photophysical properties and device performance. Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2017 May;178:106–13. Available from: <URL>.
  • 23. Lee C-P, Lin RY-Y, Lin L-Y, Li C-T, Chu T-C, Sun S-S, et al. Recent progress in organic sensitizers for dye-sensitized solar cells. RSC Adv [Internet]. 2015;5(30):23810–25. Available from: <URL>.
  • 24. Chang YJ, Chow TJ. Highly efficient triarylene conjugated dyes for sensitized solar cells. J Mater Chem [Internet]. 2011;21(26):9523–31. Available from: <URL>.
  • 25. Chen D-Y, Hsu Y-Y, Hsu H-C, Chen B-S, Lee Y-T, Fu H, et al. Organic dyes with remarkably high absorptivity; all solid-state dye sensitized solar cell and role of fluorine substitution. Chem Commun [Internet]. 2010;46(29):5256–8. Available from: <URL>.
  • 26. Chen B-S, Chen D-Y, Chen C-L, Hsu C-W, Hsu H-C, Wu K-L, et al. Donor–acceptor dyes with fluorine substituted phenylene spacer for dye-sensitized solar cells. J Mater Chem [Internet]. 2011;21(6):1937–45. Available from: <URL>.
  • 27. Wang Z-S, Cui Y, Dan-oh Y, Kasada C, Shinpo A, Hara K. Thiophene-Functionalized Coumarin Dye for Efficient Dye-Sensitized Solar Cells:  Electron Lifetime Improved by Coadsorption of Deoxycholic Acid. J Phys Chem C [Internet]. 2007 May 1;111(19):7224–30. Available from: <URL>.
  • 28. Yang H-Y, Yen Y-S, Hsu Y-C, Chou H-H, Lin JT. Organic Dyes Incorporating the Dithieno[3,2- b :2′,3′- d ]thiophene Moiety for Efficient Dye-Sensitized Solar Cells. Org Lett [Internet]. 2010 Jan 1;12(1):16–9. Available from: <URL>.
  • 29. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 16 Rev. C. 01, Wallingford, CT. Wallingford, CT. 2016;
  • 30. Chen X, Jia C, Wan Z, Yao X. Organic dyes with imidazole derivatives as auxiliary donors for dye-sensitized solar cells: Experimental and theoretical investigation. Dye Pigment [Internet]. 2014 May;104:48–56. Available from: <URL>.
  • 31. Aulakh RK, Sandhu S, Tanvi, Kumar S, Mahajan A, Bedi RK, et al. Designing and synthesis of imidazole based hole transporting material for solid state dye sensitized solar cells. Synth Met [Internet]. 2015 Jul;205:92–7. Available from: <URL>.
  • 32. Duvva N, Eom YK, Reddy G, Schanze KS, Giribabu L. Bulky Phenanthroimidazole–Phenothiazine D−π–A Based Organic Sensitizers for Application in Efficient Dye-Sensitized Solar Cells. ACS Appl Energy Mater [Internet]. 2020 Jul 27;3(7):6758–67. Available from: <URL>.
There are 32 citations in total.

Details

Primary Language English
Subjects Organic Chemical Synthesis
Journal Section RESEARCH ARTICLES
Authors

Saifaldeen Abdalhadi 0000-0003-4057-3893

Nabeel Mohammed This is me 0000-0002-4056-0788

Khalida Ali This is me 0000-0002-0386-6446

Hazim Al-zubaidi 0000-0002-7275-1175

Publication Date February 4, 2024
Submission Date September 5, 2023
Acceptance Date October 16, 2023
Published in Issue Year 2024 Volume: 11 Issue: 1

Cite

Vancouver Abdalhadi S, Mohammed N, Ali K, Al-zubaidi H. Investigating the Effects of Fluorine Substituents on Organic Dyes in Dye-Sensitized Solar Cells. JOTCSA. 2024;11(1):1-10.