Synthesis and Characterization of 2,3-Diaminomaleonitrile Derivatives by One-Pot Schiff Base Reaction and Their Application in Dye Synthesized Solar Cells

https://doi.org/10.22146/ijc.57535

Saifaldeen Muwafag Abdalhadi(1*), Asmaa Yahya Al-Baitai(2), Hazim Abdulrazzaq Al-Zubaidi(3)

(1) Department of Remote Sensing, College of Remote Sensing and Geophysics, Al-Karkh University of Science, Baghdad, Iraq
(2) Department of Chemistry, College of Science, Al-Nahrain University, Baghdad, Iraq
(3) Department of biomedical science, College of Science, Al-Karkh University of Science, Baghdad, Iraq
(*) Corresponding Author

Abstract


In a one-pot reaction, three new 2,3-diaminomaleonitrile (DAMN) derivative dyes were prepared by simple Schiff base reaction. The compounds were designed as a sensitizer in dye synthesizes solar cells (DSSCs). Many conditions have been used to provide the methodology to get the best yield. The prepared dyes were characterized by melting point, elemental microanalysis, mass spectroscopy, FT-IR, 1H-NMR, and UV-Vis spectroscopy. A computational study was carried out to support our results. The DSSC data was shown the best performance for SA3 dye with 0.38% efficiency at AM 1.5 then SA2 with 0.22% and the last dye is SA1 with 0.09%, compared to control cell (N719) 5.4%.

Keywords


one-pot reaction; 2,3-diaminomaleonitrile; Schiff base; DSSCs



References

[1] Singh, G.K., 2013, Solar power generation by PV (photovoltaic) technology: A review, Energy, 53, 1–13.

[2] Gong, J., Sumathy, K., Qiao, Q., and Zhou, Z., 2017, Review on dye-sensitized solar cells (DSSCs): Advanced techniques and research trends, Renewable Sustainable Energy Rev., 68, 234–246.

[3] Malinowski, M., Leon, J.I., and Abu-Rub, H., 2017, Solar photovoltaic and thermal energy systems: Current technology and future trends, Proc. IEEE, 105 (11), 2132–2146.

[4] Abdalhadi, S.M., Connell, A., Zhang, X., Wiles, A.A., Davies, M.L., Holliman, P.J., and Cooke, G., 2016, Convenient synthesis of EDOT-based dyes by CH-activation and their application as dyes in dye-sensitized solar cells, J. Mater. Chem. A, 4 (40), 15655–15661.

[5] Shalini, S., Balasundaraprabhu, R., Kumar, T.S., Prabavathy, N., Senthilarasu, S., and Prasanna, S., 2016, Status and outlook of sensitizers/dyes used in dye sensitized solar cells (DSSC): A review, Int. J. Energy Res., 40 (10), 1303–1320.

[6] Prabavathy, N., Shalini, S., Balasundaraprabhu, R., Velauthapillai, D., Prasanna, S., and Muthukumarasamy, N., 2017, Enhancement in the photostability of natural dyes for dye-sensitized solar cell (DSSC) applications: A review, Int. J. Energy Res., 41 (10), 1372–1396.

[7] Sugathan, V., John, E., and Sudhakar, K., 2015, Recent improvements in dye sensitized solar cells: A review, Renewable Sustainable Energy Rev., 52, 54–64.

[8] Ahmad, M.S., Pandey, A.K., and Abd Rahim, N., 2017, Advancements in the development of TiO2 photoanodes and its fabrication methods for dye sensitized solar cell (DSSC) applications. A review, Renewable Sustainable Energy Rev., 77, 89–108.

[9] Mozaffari, S., Nateghi, M.R., and Zarandi, M.B., 2017, An overview of the Challenges in the commercialization of dye sensitized solar cells, Renewable Sustainable Energy Rev., 71, 675–86.

[10] Urbani, M., Grätzel, M., Nazeeruddin, M.K., and Torres, T., 2014, Meso-substituted porphyrins for dye-sensitized solar cells, Chem. Rev., 114 (24), 12330–12396.

[11] Obotowo, I.N., Obot, I.B., and Ekpe, U.J., 2016, Organic sensitizers for dye-sensitized solar cell (DSSC): Properties from computation, progress and future perspectives, J. Mol. Struct., 1122, 80–87.

[12] Carella, A., Borbone, F., and Centore, R., 2018, Research progress on photosensitizers for DSSC, Front. Chem., 6, 113–127.

[13] Ludin, N.A., Al-Alwani Mahmoud, A.M., Mohamad, A.B., Kadhum, A.A.H., Sopian, K., and Abdul Karim, N.S., 2014, Review on the development of natural dye photosensitizer for dye-sensitized solar cells, Renewable Sustainable Energy Rev., 31, 386–396.

[14] O'Regan, B., and Grätzel, M., 1991, A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films, Nature, 353 (6346), 737–740.

[15] Nazeeruddin, M.K., Péchy, P., Renouard, T., Zakeeruddin, S.M., Humphry-Baker, R., Comte, P., Liska, P., Cevey, L., Costa, E., Shklover, V., Spiccia, L., Deacon, G.B., Bignozzi, C.A., and Grätzel, M., 2001, Engineering of efficient panchromatic sensitizers for nanocrystalline TiO2-based solar cells, J. Am. Chem. Soc., 123 (8), 1613–1624.

[16] Kim, B.G., Zhen, C.G., Jeong, E.J., Kieffer, J., and Kim, J., 2012, Organic dye design tools for efficient photocurrent generation in dye-sensitized solar cells: Exciton binding energy and electron acceptors, Adv. Funct. Mater., 22 (8), 1606–1612.

[17] Choi, H., Baik, C., Kang, S.O., Ko, J., Kang, M.S., Nazeeruddin, M.K., and Grätzel, M., 2008, Highly efficient and thermally stable organic sensitizers for solvent-free dye-sensitized solar cells, Angew. Chem. Int. Ed., 47 (2), 327–330.

[18] Lin, R.Y.Y., Wu, F.L., Li, C.T., Chen, P.Y., Ho, K.C., and Lin, J.T., 2015, High-performance aqueous/organic dye-sensitized solar cells based on sensitizers containing triethylene oxide methyl ether, ChemSusChem, 8 (15), 2503–2513.

[19] Hara, K., Sato, T., Katoh, R., Furube, A., Ohga, Y., Shinpo, A., Suga, S., Sayama, K., Sugihara, H., and Arakawa, H., 2003, Molecular design of coumarin dyes for efficient dye-sensitized solar cells, J. Phys. Chem. B, 107 (2), 597–606.

[20] Jiao, Y., Zhang, F., Grätzel, M., and Meng, S., 2013, Structure-property relations in all-organic dye-sensitized solar cells, Adv. Funct. Mater., 23 (4), 424–429.

[21] Mishra, A., Fischer, M.K.R., and Bäuerle, P., 2009, Metal-free organic dyes for dye-sensitized solar cells: From structure: Property relationships to design rules, Angew. Chem. Int. Ed., 48 (14), 2474–2499.

[22] El-Meligy, A.B., Koga, N., Iuchi, S., Yoshida, K., Hirao, K., Mangood, A.H., and El-Nahas, A.M., 2018, DFT/TD-DFT calculations of the electronic and optical properties of bis-N,N-dimethylaniline-based dyes for use in dye-sensitized solar cells, J. Photochem. Photobiol., A, 367, 332–346.

[23] Naik, P., Su, R., Babu, D.D., El-Shafei, A., and Adhikari, A.V., 2017, Structurally simple D–A-type organic sensitizers for dye-sensitized solar cells: Effect of anchoring moieties on the cell performance, J. Iran. Chem. Soc., 14 (11), 2457–2466.

[24] Hara, K., Sato, T., Katoh, R., Furube, A., Yoshihara, T., Murai, M., Kurashige, M., Ito, S., Shinpo, A., Suga, S., and Arakawa, H., 2005, Novel conjugated organic dyes for efficient dye-sensitized solar cells, Adv. Funct. Mater., 15 (2), 246–252.

[25] Sánchez-de-Armas, R., San Miguel, M.Á., Oviedo, J., and Sanz, J.F., 2012, Coumarin derivatives for dye sensitized solar cells: A TD-DFT study, Phys. Chem. Chem. Phys., 14 (1), 225–233.

[26] Wang, Z.S., Cui, Y., Hara, K., Dan-oh, Y., Kasada, C., and Shinpo, A., 2007, A high-light-harvesting-efficiency coumarin dye for stable dye-sensitized solar cells, Adv. Mater., 19 (8), 1138–1141.

[27] Wang, Z.S., Cui, Y., Dan-oh, Y., Kasada, C., Shinpo, A., and Hara, K., 2007, Thiophene-functionalized coumarin dye for efficient dye-sensitized solar cells:  Electron lifetime improved by coadsorption of deoxycholic acid, J. Phys. Chem. C, 111 (19), 7224–7230.

[28] Cariello, M., Abdalhadi, S.M., Yadav, P., Decoppet, J.D., Zakeeruddin, S.M., Grätzel, M., Hagfeldt, A., and Cooke, G., 2018, An investigation of the roles furan versus thiophene π-bridges play in donor–π-acceptor porphyrin based DSSCs, Dalton Trans., 47 (18), 6549–6556.

[29] Gao, P., Tsao, H.N., Yi, C., Grätzel, M., and Nazeeruddin, M.K., 2014, Extended π‐bridge in organic dye‐sensitized solar cells: The longer, the better?, Adv. Energy Mater., 4 (7), 1301485.

[30] Tsuzuki, K., and Tada, M., 1986, The syntheses of pteridin-2-one derivatives from diaminomaleonitrile (DAMN), J. Heterocycl. Chem., 23 (5), 1299–1301.

[31] Zhou, H., Wang, J., Chen, Y., Xi, W., Zheng, Z., Xu, D., Cao, Y., Liu, G., Zu, W., Wu, J., and Tian, Y., 2013, New diaminomaleonitrile derivatives containing aza-crown ether: Selective, sensitive and colorimetric chemosensors for Cu(II), Dyes Pigm., 98 (1), 1–10.

[32] Anitha, C., Sheela, C.D., Tharmaraj, P., and Shanmugakala, R., 2013, Studies on synthesis and spectral characterization of some transition metal complexes of azo-azomethine derivative of diaminomaleonitrile, Int. J. Inorg. Chem., 2013, 436275.

[33] Aruna, Rani, B., Swami, S., Agarwala, A., Behera, D., and Shrivastava, R., 2019, Recent progress in development of 2,3-diaminomaleonitrile (DAMN) based chemosensors for sensing of ionic and reactive oxygen species, RSC Adv., 9 (52), 30599–30614.

[34] Li, Z., Liu, C., Wang, J., Wang, S., Xiao, L., and Jing, X., 2019, A selective diaminomaleonitrile-based dual channel emissive probe for Al3+ and its application in living cell imaging, Spectrochim. Acta, Part A, 212, 349–355.

[35] Fuse, S., Sugiyama, S., Maitani, M.M., Wada, Y., Ogomi, Y., Hayase, S., Katoh, R., Kaiho, T., and Takahashi, T., 2014, Elucidating the structure–property relationships of donor–π-acceptor dyes for dye-sensitized solar cells (DSSCs) through rapid library synthesis by a one-pot procedure, Chem. Eur. J., 20 (34), 10685–10694.

[36] Matsumura, K., Yoshizaki, S., Maitani, M.M., Wada, Y., Ogomi, Y., Hayase, S., Kaiho, T., Fuse, S., Tanaka, H., and Takahashi, T., 2015, Rapid synthesis of thiophene-based, organic dyes for dye-sensitized solar cells (DSSCs) by a one-pot, four-component coupling approach, Chem. Eur. J., 21 (27), 9742–9747.

[37] Irie, S., Fuse, S., Maitani, M.M., Wada, Y., Ogomi, Y., Hayase, S., Kaiho, T., Masui, H., Tanaka, H., and Takahashi, T., 2016, Rapid synthesis of D-A′-π-A dyes through a one-pot three-component Suzuki–Miyaura coupling and an evaluation of their photovoltaic properties for use in dye-sensitized solar cells, Chem. Eur. J., 22 (7), 2507–2514.

[38] Lee, C., Yang, W., and Parr, R.G., 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B: Condens. Matter, 37 (2), 785–789.

[39] Becke, A.D., 1993, Density‐functional thermochemistry. III. The role of exact exchange, J. Chem. Phys., 98 (7), 5648–5652.

[40] Qu, S., Wang, B., Guo, F., Li, J., Wu, W., Kong, C., Long, Y., and Hua, J., 2012, New diketo-pyrrolo-pyrrole (DPP) sensitizer containing a furan moiety for efficient and stable dye-sensitized solar cells, Dyes Pigm., 92 (3), 1384–1393.



DOI: https://doi.org/10.22146/ijc.57535

Article Metrics

Abstract views : 761 | views : 465 | views : 260


Copyright (c) 2020 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.