5,6,7-Trimethoxy-2-(Methylthio)Quinoline with Different Anchoring Groups: Synthesis And Dye-Sensitized Solar Cell Applications

Two new metal-free organic dyes in D-π-A structure, containing a quinoline π-bridge and malononitrile (4a) and cyanoacrylic acid (4b) as acceptors, were synthesized for the first time to apply dye-sensitized solar cell (DSSC). The structures of these compounds were elucidated by FT-IR, 1H NMR, 13C NMR techniques. The photophysical and photovoltaic properties of the obtained compounds were investigated and compared by current density–voltage (J–V) graphs. Compound 4b containing cyanoacrylic acid as an acceptor reached an open–circuit voltage (Voc) of 0.645 V, short–circuit current density (Jsc) of 6.66 mA cm-2 and fill factor (FF) of 0.70 in the presence of chenodeoxycholic acid (CDCA), showing a power conversion efficiency (PCE) of 3.01%. It is also observed that the incorporation of thiomethyl group to the structure instead of methoxy group increases the PCE.

Keywords:

Dye-sensitized solar cells, metal free dyes, quinoline thiomethyl group,

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[1]B. O’Regan and M. Gratzel, “A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films,” Nature, vol. 353, pp. 737-740, 1991.
[2] P. Li, Z. Wang, C. Song, and H. Zhang, “Rigid fused π-spacers in D-π-A type molecules for dye-sensitized solar cells: A computational investigation,” Journal of Materials Chemistry C, vol. 5, pp. 11454-11465, 2017.
[3] H. Huang, H. Chen, J. Long, G. Wang, and S. Tan, “Novel D-A-p-A organic dyes based on 3-dimensional triarylamine and benzothiadiazole derivatives for high-performance dye-sensitized solar cells,” Journal of Power Sources, vol. 326, pp. 438–446, 2016.
[4] M. M. Jadhav, J. V. Vaghasiya, D. Patil, S. S. Soni, and N. Sekar, “Synthesis of novel colorants for DSSC to study effect of alkyl chain length alteration of auxiliary donor on light to current conversion efficiency,” Journal of Photochemistry and Photobiology A, vol. 377, pp. 119-129, 2019.
[5] J. Zhang, Y. H. Kan, H. B. Li, Y. Geng, Y. Wu, and Z. M. Su, “How to design proper π-spacer order of the D-π-A dyes for DSSCs? A density functional response,” Dyes Pigments, vol. 95, pp. 313-321, 2012.
[6] Y. S. Yen, J. S. Ni, W. I Hung, C. Y. Hsu, H. H. Chou, and J. T. Lin, “Naphtho[2,3-c][1,2,5]thiadiazole and 2H-Naphtho[2,3-d][1,2,3]triazole-containing D-A-π-A conjugated organic dyes for dye-sensitized solar cells,” ACS Applied Materials & Interfaces, vol. 8, pp. 6117-6126, 2016.
[7] N. Zhou, K. Prabakaran, B. Lee, S. H. Chang, B. Harutyunyan, P. Guo, M. R. Butler, A. Timalsina, M. J. Bedzyk, M. A. Ratner, S. Vegiraju, S. Yau, C. G. Wu, R. P. H. Chang, A. Facchetti, M. C. Chen, and T. J. Marks, “Metal-free tetrathienoacene sensitizers for high-performance dye-sensitized solar cells,” Journal of the American Chemical Society, vol. 137, pp. 4414-4423, 2015.
[8] B. S. Arslan, S. N. Ülüş, M. Gezgin, B. Arkan, E. Güzel, D. Avcı, M. Nebioğlu, and İ. Şişman, “Insight into the effects of the donors and pi-spacers on the photovoltaic performance of quinoline and pyridocarbazole based DSSCs,” Optical Materials, vol. 106, pp. 109974, 2020.
[9] O. O. Ajani, K. T. Iyaye, O. Y. Audu, S. J. Olorunshola, A. O. Kuye, and I. O. Olanrewaju, “Microwave assisted synthesis and antimicrobial potential of quinoline based 4-hydrazide-hydrazone derivatives,” Journal of Heterocyclic Chemistry, vol. 55, pp. 302-312, 2017.
[10] P. Pounraj, V. Mohankumar, M. S. Pandian, and P. Ramasamy, “Donor functionalized quinoline based organic sensitizers for dye sensitized solar cell (DSSC) applications: DFT and TD-DFT investigations,” Journal of Molecular Modeling, vol. 24, pp. 343, 2018.
[11] G. C. dos Santos, E. F. Oliveira, F. C. Lavarda, and L. C. da Silva-Filho, “Designing new quinoline-based organic photosensitizers for dye-sensitized solar cells (DSSC): a theoretical investigation,” Journal of Molecular Modeling, vol. 25, pp. 75, 2019.
[12] A. Slodek, M. Matussek, M. Filapek, G. Szafraniec-Gorol, A. Szlapa, I. Grudzka-Flak, M. Szczurek, J. G. Malecki, A. Maron, E. Schab-Balcerzak, E. M. Nowak, J. Sanetra, M. Olejnik, W. Danikiewicz, and S. Krompiec, “Small donor–acceptor molecules based on a quinoline–fluorene system with promising photovoltaic properties,” European Journal of Organic Chemistry, vol. 14, pp. 2500-2508, 2016.
[13] P. Singh, V. Srivastava, and M. A. Quraishi, “Novel quinoline derivatives as green corrosion inhibitors for mild steel in acidic medium: Electrochemical, SEM, AFM, and XPS studies,” Journal of Molecular Liquids, vol. 216, pp. 164-173, 2016.
[14] M. Mao, X. Zhang, B. Zhu, J. Wang, G. Wu, Y. Yin, and Q. Song, “Comparative studies of organic dyes with a quinazoline or quinoline chromophore as π-conjugated bridges for dye-sensitized solar cells,” Dyes Pigments, vol. 124, pp. 72-81, 2016.
[15] B. S. Arslan, E. Güzel, T. Kaya, V. Durmaz, M. Keskin, D. Avcı, M. Nebioğlu, and İ. Şişman, “Novel D-π-A organic dyes for DSSCs based on dibenzo[b,h][1,6] naphthyridine as a π-bridge,” Dyes Pigments, vol. 164, pp. 188-197, 2019.
[16] B.S. Arslan, B. Arkan, M. Gezgin, Y. Derin, D. Avcı, A. Tutar, M. Nebioğlu, and İ. Şişman, “The improvement of photovoltaic performance of quinoline-based dye-sensitized solar cells by modification of the auxiliary acceptors,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 404, pp. 112936, 2021.
[17] B. Cheng, and J. Xu, “Mechanistic insight into the thermal 1,3-chlorine migrations of N-chloroacetanilides under neutral conditions,” Phosphorus, Sulfur, and Silicon and the Related Elements, vol. 192 pp. 518–525, 2017.
[18] O. Meth-Cohn, B. Narine, and B. Tarnowski, “A versatile new synthesis of quinolines and related fused pyridines. Part 5. The synthesis of 2-chloroquinoline-3-carbaldehydes,” Journal of the Chemical Society Perkin Transactions 1, pp. 1520–1530, 1981.
[19] A. D. Sonawane, D. R. Garud, T. Udagawa, and M. Koketsu, “Synthesis of thieno [2, 3-b] quinoline and selenopheno [2, 3-b] quinoline derivatives via iodocyclization reaction and a DFT mechanistic study,” Organic & Biomolecular Chemistry, vol. 16, pp. 245-255, 2018.
[20] A. Kathiravan, M. Panneerselvam, K. Sundaravel, N. Pavithra, V. Srinivasan, S. Anandan, and M. Jaccob, “Unravelling the effect of anchoring groups on the ground and excited state properties of pyrene using computational and spectroscopic methods,” Physical Chemistry Chemical Physics, vol. 18, pp. 13332-13345, 2016.
[21] Y. Ooyama and Y. Harima, “Molecular designs and syntheses of organic dyes for dye-sensitized solar cells,” European Journal of Organic Chemistry, vol. 18, pp. 2903-2934, 2009.
[22] N. Prachumrak, T. Sudyoadsuk, A. Thangthong, P. Nalaoh, S. Jungsuttiwong, R. Daengngern, S. Namuangruk, P. Pattanasattayavong, and V. Promarak, “Improvement of D–π–A organic dye-based dye-sensitized solar cell performance by simple triphenylamine donor substitutions on the π-linker of the dye” Materials Chemistry Frontiers, vol. 1, pp. 1059-1072, 2017.