RESEARCH ARTICLE

Unravelling the bottleneck of phosphonic acid anchoring groups aiming toward enhancing the stability and efficiency of mesoscopic solar cells

  • Ajendra Kumar Vats 1 ,
  • Pritha Roy 1 ,
  • Linjun Tang 1 ,
  • Shuzi Hayase 2 ,
  • Shyam S. Pandey , 1
Expand
  • 1. Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, Kitakyushu 808-0196, Japan
  • 2. i-Powered Energy System Research Center (i-PERC), The University of Electro-Communications, Tokyo 182-8585, Japan

Received date: 22 Jun 2021

Accepted date: 07 Sep 2021

Published date: 15 Jul 2022

Copyright

2021 Higher Education Press

Abstract

Novel near-infrared sensitizers with different anchoring groups aiming toward improved stability and efficiency of dye-sensitized solar cells were synthesized. Adsorption of these dyes on the mesoporous TiO2 surface revealed the dye adsorption rate of –CH=CH–COOH (SQ-139)>–CH=C(CN)COOH (SQ-140)>–PO3H2 (SQ-143)>–CH=C(CN)PO3H2 (SQ-148)>–CH=C(CN)PO3H–C2H5 (SQ-157)>–PO3H–C2H5 (SQ-151)> –CH=CH–COOH(–PO3H2) (SQ-162). The binding strength of these dyes on mesoporous TiO2 as investigated by dye desorption studies follows SQ-162>SQ-143>SQ-148>SQ-139≫SQ-157~SQ-151≫SQ-140 order. The acrylic acid anchoring group was demonstrated to be an optimum functional group owing to its fast dye adsorption rate and better binding strength on TiO2 along with good photoconversion efficiency. Results of dye binding on TiO2 surface demonstrated that SQ-162 bearing double anchoring groups of phosphonic and acrylic acid exhibited>550 times stronger binding as compared to dye SQ-140 having cyanoacrylic acid anchoring group. SQ-140 exhibited the best photovoltaic performance with photon harvesting mainly in the far-red to near-infrared wavelength region having short circuit current density, open-circuit voltage and fill factor of 14.28 mA·cm–2, 0.64 V and 0.65, respectively, giving the power conversion efficiency of 5.95%. Thus, dye SQ-162 not only solved the problem of very poor efficiency of dye bearing only phosphonic acid while maintaining the extremely high binding strength opening the path for the design and development of novel near-infrared dyes with improved efficiency and stability by further increasing the π-conjugation.

Cite this article

Ajendra Kumar Vats , Pritha Roy , Linjun Tang , Shuzi Hayase , Shyam S. Pandey . Unravelling the bottleneck of phosphonic acid anchoring groups aiming toward enhancing the stability and efficiency of mesoscopic solar cells[J]. Frontiers of Chemical Science and Engineering, 2022 , 16(7) : 1060 -1078 . DOI: 10.1007/s11705-021-2117-z

Acknowledgments

One of the authors, SSP is thankful to the Japanese society for the promotion of science (JSPS) for the financial support by a grant-in-aid for scientific research C (Grant No. 18K05300) to carry out this research.

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-021-2117-z and is accessible for authorized users.
1
Lund H, Mathiesen B V. Energy system analysis of 100% renewable energy systems—the case of Denmark in years 2030 and 2050. Energy, 2009, 34(5): 524–531

DOI

2
Omer A M, Agric J. Environmental and socio-economic aspects of possible development in renewable energy use. Journal of Agricultural Extension and Rural Development, 2010, 2: 1–21

3
Voudoukis N F. Design, description, implementation, and assessment of a multimedia application with simulations for teaching models of light. European Journal of Electrical and Computer Engineering, 2018, 2(7): 13

DOI

4
Freitag M, Teuscher J, Saygili Y, Zhang X, Giordano F, Liska P, Hua J, Zakeeruddin S M, Moser J E, Grätzel M, . Dye-sensitized solar cells for efficient power generation under ambient lighting. Nature Photonics, 2017, 11(6): 372–378

DOI

5
O’Regan B, Grätzel M. A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature, 1991, 353(6346): 737–740

DOI

6
Ahmad M S, Pandey A K, Rahim N A. Advancements in the development of TiO2 photoanodes and its fabrication methods for dye-sensitized solar cell (DSSC) applications. A review. Renewable & Sustainable Energy Reviews, 2017, 77: 89–108

DOI

7
Wu J, Lan Z, Lin J, Huang M, Huang Y, Fan L, Luo G. Electrolytes in dye-sensitized solar cells. Chemical Reviews, 2015, 115(5): 2136–2173

DOI

8
Wu J, Lan Z, Lin J, Huang M, Huang Y, Fan L, Luo G, Lin Y, Xie Y, Wei Y. Counter electrodes in dye-sensitized solar cells. Chemical Society Reviews, 2017, 46(19): 5975–6023

DOI

9
Eom K Y, Kang S H, Choi I T, Yoo Y J, Kim J H, Kim H K. Significant light absorption enhancement by a single heterocyclic unit change in the π-bridge moiety from thieno[3,2-b]benzothiophene to thieno[3,2-b]indole for high performance dye sensitized and tandem solar cells. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2017, 5(5): 2297–2308

DOI

10
Yella A, Lee H W, Tsao H N, Yi C, Chandiran A K, Nazeeruddin M K, Diau E W G, Yeh C Y, Zakeeruddin S M, Grätzel M. Porphyrin-sensitized solar cells with cobalt(II/III)-based redox electrolyte exceed 12 percent efficiency. Science, 2011, 334(6056): 629–633

DOI

11
Kakiage K, Aoyama Y, Yano T, Otsuka T, Kyomen T, Unno M, Hanaya M. An achievement of over 12 percent efficiency in an organic dye-sensitized solar cell. Chemical Communications, 2014, 50(48): 6379–6381

DOI

12
Ji J M, Zhou H, Yu K E, Kim C H, Kim H K. 14.2% efficiency dye-sensitized solar cells by co-sensitizing novel thieno[3,2-b]indole-based organic dyes with a promising porphyrin sensitizer. Advanced Energy Materials, 2020, 15(15): 2000124

DOI

13
Mathew S, Yella A, Gao P, Baker R H, Curchod B F E, Astani N A, Tavernelli I, Rothlisberger U, Nazeeruddin M K, Grätzel M, . Dye-sensitized solar cells with 13% efficiency achieved through the molecular engineering of porphyrin sensitizers. Nature Chemistry, 2014, 6(3): 242–247

DOI

14
Zhang L, Yang X, Wang W, Gurzadyan G G, Li J, Li X, An J, Yu Z, Wang H, Cai B, et al. 13.6% efficient organic dye-sensitized solar cells by minimizing energy losses of the excited state. ACS Energy Letters, 2019, 4(4): 943–951

DOI

15
Kang S H, Jeong M J, Eom Y K, Choi I T, Kwon S M, Yoo Y J, Kim J H, Kwon J, Park J H, Kim H K. Porphyrin sensitizers with donor structural engineering for superior performance dye-sensitized solar cells and tandem solar cells for water splitting applications. Advanced Energy Materials, 2017, 7(7): 1072117

DOI

16
Pradhan A, Kiran M S, Kapil G, Hayase S, Pandey S S. Wide wavelength photon harvesting in dye-sensitized solar cells utilizing cobalt complex redox electrolyte: implication of surface passivation. Solar Energy Materials and Solar Cells, 2019, 195: 122–133

DOI

17
Baranwal A K, Shiki T, Ogomi Y, Pandey S S, Ma T, Hayase S. Tandem dye-sensitized solar cells with a back-contact bottom electrode without a transparent conductive oxide layer. RSC Advances, 2014, 4(88): 47735–47742

DOI

18
Shivashimpi G M, Pandey S S, Watanabe R, Fujikawa N, Ogomi Y, Yamaguchi Y, Hayase S. Efficient far-red sensitization of nanocrystalline TiO2 films by an unsymmetrical squaraine dye. Journal of Photochemistry and Photobiology A Chemistry, 2014, 273: 1–7

DOI

19
Murakami T N, Yoshida E, Koumura N. Carbazole dye with phosphonic acid anchoring groups for long-term heat stability of dye-sensitized solar cells. Electrochimica Acta, 2014, 131: 174–183

DOI

20
Zhang L, Cole J M. Anchoring groups for dye-sensitized solar cells. ACS Applied Materials & Interfaces, 2015, 7(6): 3427–3455

DOI

21
Brennan B J, Portole’s M J L, Liddell P A, Moore T A, Moore A L, Gust D. Comparison of silatrane, phosphonic acid, and carboxylic acid functional groups for attachment of porphyrin sensitizers to TiO2 in photoelectrochemical cells. Physical Chemistry Chemical Physics, 2013, 15(39): 16605–16614

DOI

22
Hanson K, Brennaman M K, Luo H, Glasson C R K, Concepcion J J, Song W, Meyer T J. Photostability of phosphonate-derivatized, Ru(II) polypyridyl complexes on metal oxide surfaces. ACS Applied Materials & Interfaces, 2012, 4(3): 1462–1469

DOI

23
Kakiage K, Yamamura M, Fujimura E, Kyomen T, Unno M, Hanaya M. High performance of Si–O–Ti bonds for anchoring sensitizing dyes on TiO2 electrodes in dye-sensitized solar cells evidenced by using alkoxysilylazobenzenes. Chemistry Letters, 2010, 39(3): 260–262

DOI

24
Higashino T, Nimura S, Sugiura K, Kurumisawa Y, Tsuji Y, Imahori H. Photovoltaic properties and long-term durability of porphyrin-sensitized solar cells with silicon-based anchoring groups. ACS Omega, 2017, 2(10): 6958–6967

DOI

25
Vats A K, Pradhan A, Hayase S, Pandey S S. Synthesis, photophysical characterization and dye adsorption behaviour in unsymmetrical squaraine dyes with varying anchoring groups. Journal of Photochemistry and Photobiology A Chemistry, 2020, 394: 112467

DOI

26
Baktash A, Khoshnevisan B, Sasani A, Mirabbaszadeh K. Effects of carboxylic acid and phosphonic acid anchoring groups on the efficiency of dye sensitized solar cells: a computational study. Organic Electronics, 2016, 33: 207–212

DOI

27
Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A D J, . Gaussian 09. Revision A.02, Gaussian, Inc., Wallingford CT, 2009

28
Shivashimpi G M, Pandey S S, Watanabe R, Fujikawa N, Ogomi Y, Yamaguchi Y, Hayase S. Novel unsymmetrical squaraine dye bearing cyanoacrylic acid anchoring group and its photosensitization behavior. Tetrahedron Letters, 2012, 53(40): 5437–5440

DOI

29
Li J, Chen C Y, Ho W C, Chen S H, Wu C G. Unsymmetrical squaraines incorporating quinoline for near-infrared responsive dye-sensitized solar cells. Organic Letters, 2012, 14(21): 5420–5423

DOI

30
Chen Y H, Qi L W, Fang F, Tan B. Organocatalytic atroposelective arylation of 2-naphthylamines as a practical approach to axially chiral biaryl amino alcohols. Angewandte Chemie, 2017, 56(51): 16308–16312

DOI

31
Brown D G, Schauer P A, Garcia J B, Fancy B R, Berlinguette C P. Stabilization of ruthenium sensitizers to TiO2 surfaces through cooperative anchoring groups. Journal of the American Chemical Society, 2013, 135(5): 1692–1695

DOI

32
Yum J H, Moon S J, Baker R H, Walter P, Geiger T, Nüesch F, Grätzel M, Nazeeruddin M K. Effect of coadsorbent on the photovoltaic performance of squaraine sensitized nanocrystalline solar cells. Nanotechnology, 2008, 19(42): 424005

DOI

33
Shivashimpi G M, Pandey S S, Hayat A, Fujikawa N, Ogomi Y, Yamaguchi Y, Hayase S. Far-red sensitizing octatrifluorobutoxy phosphorous triazatetrabenzocorrole: synthesis, spectral characterization, and aggregation studies. Journal of Photochemistry and Photobiology A Chemistry, 2014, 289: 53–59

DOI

34
Ren T B, Xu W, Zhang W, Zhang X X, Wang Z Y, Xiang Z, Yuan L, Zhang X B. A general method to increase stokes shift by introducing alternating vibronic structures. Journal of the American Chemical Society, 2018, 140(24): 7716–7722

DOI

35
Inoue T, Pandey S S, Fujikawa N, Yamaguchi Y, Hayase S. Synthesis and characterization of squaric acid-based NIR dyes for their application towards dye-sensitized solar cells. Journal of Photochemistry and Photobiology A Chemistry, 2010, 213(1): 23–29

DOI

36
Li L, Xie Z X, Wang Y L. Wang, Xu H, Xu T M, Zhang Z G, Zhang H L. Expanding the photoresponse range of TiO2 nanotube arrays by CdS/CdSe/ZnS quantum dots co-modification. Journal of Photochemistry and Photobiology A Chemistry, 2011, 224(1): 25–30

DOI

37
Ogomi Y, Kato T, Hayase S. Dye-sensitized solar cells consisting of ionic liquid and solidification. Journal of Photopolymer Science and Technology, 2006, 19(3): 403–408

DOI

38
Pastore M, Fantacci S, Angelis F D. Modeling excited states and alignment of energy levels in dye-sensitized solar cells: successes, failures, and challenges. Journal of Physical Chemistry C, 2013, 117(8): 3685–3700

DOI

39
Nazeeruddin M K, Angelis F D, Fantacci S, Selloni A, Viscardi G, Liska P, Ito S, Takeru B, Grätzel M. Combined experimental and DFT-TDDFT computational study of photoelectrochemical cell ruthenium sensitizers. Journal of the American Chemical Society, 2005, 127(48): 16835–16847

DOI

40
Improta R, Barone V, Scalmani G, Frisch M J. A state-specific polarizable continuum model time-dependent density functional theory method for excited-state calculations in solution. Journal of Chemical Physics, 2006, 125(5): 054103

DOI

41
Pandey S S, Morimoto T, Fujikawa N, Hayase S. Combined theoretical and experimental approaches for the development of squaraine dyes with small energy barrier for electron injection. Solar Energy Materials and Solar Cells, 2017, 159: 625–632

DOI

42
Pradhan A, Morimoto T, Saikiran M, Kapil G, Hayase S, Pandey S S. Investigation of the minimum driving force for dye regeneration utilizing model squaraine dyes for dye-sensitized solar cells. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2017, 5(43): 22672–22682

DOI

43
Park H, Bae E, Lee J J, Park J, Choi W. Effect of the anchoring group in Ru-bipyridyl sensitizers on the photoelectrochemical behavior of dye-sensitized TiO2 electrodes: carboxylate versus phosphonate linkages. Journal of Physical Chemistry B, 2006, 110(17): 8740–8749

DOI

44
Johansson V, Gibbings L E, Clarke T, Gorlov M, Andersson G G, Kloo L. On the correlation between dye coverage and photoelectrochemical performance in dye-sensitized solar cells. Journal of the Chemical Society, Faraday Transactions, 2014, 16: 711–718

45
Khazraji A C, Hotchandani S, Das S, Kamat P V. Controlling dye (merocyanine-540) aggregation on nanostructured TiO2 films. An organized assembly approach for enhancing the efficiency of photosensitization. Journal of Physical Chemistry B, 1999, 103(22): 4693–4700

DOI

46
Nazeeruddin M K, Baker R H, Liska P, Grätzel M. Investigation of sensitizer adsorption and the influence of protons on current and voltage of a dye-sensitized nanocrystalline TiO2 solar cell. Journal of Physical Chemistry B, 2003, 107(34): 8981–8987

DOI

47
Kawano M, Nishiyama T, Ogomi Y, Pandey S S, Ma T, Hayase S. Relationship between diffusion of Co3+/Co2+ redox species in nanopores of porous titania stained with dye molecules, dye molecular structures, and photovoltaic performances. RSC Advances, 2015, 5(102): 83725–83731

DOI

48
Franz R G. Comparisons of pKa and log P values of some carboxylic and phosphonic acids: synthesis and measurement. AAPS PharmSci, 2001, 3(2): 1–13

DOI

49
Guerrero G, Alauzun J G, Granier M, Laurencin D, Mutin P H. Phosphonate coupling molecules for the control of surface/interface properties and the synthesis of nanomaterials. Dalton Transactions (Cambridge, England), 2013, 42(35): 12569–12585

DOI

Outlines

/