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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

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Front. Chem. Sci. Eng.    2022, Vol. 16 Issue (7) : 1060-1078    https://doi.org/10.1007/s11705-021-2117-z
RESEARCH ARTICLE
Unravelling the bottleneck of phosphonic acid anchoring groups aiming toward enhancing the stability and efficiency of mesoscopic solar cells
Ajendra Kumar Vats1, Pritha Roy1, Linjun Tang1, Shuzi Hayase2, Shyam S. Pandey1()
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
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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.
Keywords anchoring groups      adsorption behaviour      dye-binding strength      squaraine dyes      dye-sensitized solar cells     
Corresponding Author(s): Shyam S. Pandey   
Online First Date: 25 November 2021    Issue Date: 15 July 2022
 Cite this article:   
Ajendra Kumar Vats,Pritha Roy,Linjun Tang, et al. Unravelling the bottleneck of phosphonic acid anchoring groups aiming toward enhancing the stability and efficiency of mesoscopic solar cells[J]. Front. Chem. Sci. Eng., 2022, 16(7): 1060-1078.
 URL:  
https://academic.hep.com.cn/fcse/EN/10.1007/s11705-021-2117-z
https://academic.hep.com.cn/fcse/EN/Y2022/V16/I7/1060
Fig.1  Chemical structure of squaraine dyes bearing varying anchoring groups. Dye SQ-143 has been already reported and used as a reference compound for the performance comparison of the sensitizers used in this work.
  Scheme 1 Synthetic scheme for the preparation of SQ-151, SQ-140, SQ-148, and SQ-157 unsymmetrical squaraine dyes bearing different anchoring groups. (a) n-butanol, toluene, reflux, 6–8 h; (b) bromotrimethylsilane (TMSBr), dichloromethane (DCM), room temperature, 36 h; (c) 3-methyl-2-butanone, ethanol, acetic acid, reflux, 12 h; (d) 1-iodoethane, acetonitrile, reflux, 24 h; (e) 2 N NaOH, toluene, room temperature, 2 h; (f) diisobutylaluminium (DIBAL), DCM, room temperature, 12 h; (g) tert-butyl cyanoacetate, piperidine, acetonitrile, reflux, 7–8 h; (h) trifluoroacetic acid (TFA), room temperature, 6–8 h; (i) diethylcyanomethylphosphonate, piperidine, acetonitrile, reflux, 7–8 h; (j) TMSBr (1 equivalent), DCM, room temperature, 12 h; (k) TMSBr (0.5 equivalent), DCM, room temperature, 36 h.
  Scheme 2 Synthetic scheme for the preparation of SQ-139 and SQ-162 unsymmetrical squaraine dyes bearing different anchoring groups. (a) NaNO2, SnCl2, concentrated HCl, 0 °C, 12 h; (b) 3-methyl-2-butanone, acetic acid, reflux, 12 h; (c) ethyl acrylate, Pd(OAc)2, P(O-tol)3, trimethylamine (TEA), DMF, high pressures reaction tube, 130 °C, 10–12 h; (d) 1-iodoethane, acetonitrile, reflux, 24 h; (e) n-butanol, toluene, reflux, 6–8 h; (f) 4 N NaOH, ethanol, reflux, 1 h; (g) NaHSO3, liquid ammonia, high-pressure reaction tube, 150 °C, 24 h; (h) 1-iodododecane, propionitrile, reflux, 48 h; (i) diethylsquarate, TEA, ethanol, reflux, 12 h; (j) TMSBr, DCM, room temperature, 12 h.
Fig.2  Electronic absorption and normalized absorption spectra (in the inset) of different squaraine dyes in (a) ethanol solution. Fluorescence emission spectra of the same in (b) the ethanol solution. In both of the measurements dye concentration was 5 µmol·L–1.
Fig.3  Normalized adsorption spectra of sensitizing dyes adsorbed on the thin films (4 μm) of transparent mesoporous TiO2.
Sensitizing dye ϵa)/(dm3·mol–1·cm–1) Absmaxb)/nm (solution) Emmaxc)/nm (solution) Stokes shiftd)/nm Absmaxe)/nm (on TiO2) Eoptf)/eV
SQ-139 2.60 × 105 665 676 11 667 721 nm (1.72 eV)
SQ-140 3.40 × 105 670 684 14 678 740 nm (1.67 eV)
SQ-143 2.48 × 105 654 668 14 660 710 nm (1.75 eV)
SQ-148 1.68 × 105 668 676 8 680 734 nm (1.68 eV)
SQ-151 1.36 × 105 652 662 10 650 687 nm (1.80 eV)
SQ-157 2.02 × 105 668 680 12 669 705 nm (1.75 eV)
SQ-162 1.18 × 105 665 668 3 664 741 nm (1.67 eV)
Tab.1  Optical parameters for unsymmetrical squaraine dyes in ethanol solution and dyes adsorbed on the thin films of TiO2
Fig.4  Energy band diagram for the sensitizing dyes taken into consideration. Theoretically calculated values after TD-DFT calculation are shown in the parentheses.
Fig.5  Results of calculated electron density in the HOMO (bottom) and LUMO (top) after structural optimization using B3PW91 functional under the TD-DFT and 6-311G basis set.
Fig.6  Dye adsorption behavior of squaraine dyes on the thin films (4 µm) of transparent TiO2.
Sensitizing dyes Adsorption rate/(abs.·min–1) Desorption rate/(nmol·cm–2·µm–1·min–1) Dye loading /(nmol·cm–2) Desorbed dye@30 min/(nmol·cm–2)
SQ-139 5.4 × 10−2 1.2 × 10−2 48.9 3.5
SQ-140 4.5 × 10−2 0.21 62.9 62.8
SQ-143 3.1 × 10−2 8.9 × 10−4 142.9 0.3
SQ-148 3.5 × 10−2 5.5 × 10−3 100.4 1.7
SQ-151 5.3 × 10−3 5.6 × 10−2 39.2 17.1
SQ-157 1.0 × 10−2 1.5 × 10−2 10.1 4.5
SQ-162 (I) 6.5 × 10−4
(II) 5.0 × 10−3		 1.1 × 10−3 192.7 0.4
Tab.2  Adsorption and desorption behavior of sensitizing dyes on to the mesoporous TiO2
Fig.7  Effect of structure of the anchoring group of dyes on their binding strength on TiO2. Dye desorption was conducted in the solution of acetonitrile-water (1:1) mixture for 30 min at room temperature. Area (6.25 cm2) and thickness of the mesoporous TiO2 (10 µm) were kept the same for all of the dyes.
Fig.8  Photovoltaic characteristics of DSSCs fabricated using squaraine dyes under (a) 1 sun simulated solar irradiation and photocurrent action spectra of (b) the same after monochromatic light illumination.
Sensitizing dyes Jsc/(mA·cm–2) Voc/V FF PCE/%
SQ-139 11.56 (9.79) 0.65 0.59 4.49
SQ-140 14.28 (11.19) 0.64 0.65 5.95
SQ-143 2.83 (2.42) 0.53 0.56 0.83
SQ-148 3.24 (2.49) 0.51 0.55 0.93
SQ-151 5.38 (4.08) 0.57 0.57 1.77
SQ-157 6.25 (3.09) 0.58 0.56 2.07
SQ-162 8.28 (7.18) 0.56 0.62 2.87
Tab.3  Photovoltaic parameters for DSSCs fabricated using various unsymmetrical squaraine dyes under 1 sun solar irradiation a)
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