Abstract
Four new molecules namely bis (5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene) di-malononitrile (NDM-1), 3-fluorothiophen-2-yl) methylene)-5, 6-difluoro-3-oxo-2, 3-dihydro-1H-inden-1-ylidene) acetate (NDM-2), 5, 6-difluoro-3-oxo-2, 3-dihydro-1H-inden-1-ylidene)-3-methyl-2-thioxothiazolidin-4-ylidene) malononitrile (NDM-3) and bis (1-methyl-2, 6-dioxo-1, 2, 5, 6-tetrahydropyridine-3-carbonitrile) (NDM-4) contains central Naphthalene Di-Imide unit with different end cap acceptors have been designed for enhance the photovoltaic efficiencies. Absorption values of designed molecules lies between 400 and 490 nm, re-organization energy values varies from 0.41 to 0.67 eV for electron and 0.49 eV to 1.25 eV for hole transfer, open circuit voltages range from 4.39 to 4.73 V which indicates their better photovoltaic properties as compared to the R (3-methyl-4-oxo-2-thioxothiazolidin-5-ylidene) methyl). Designed molecules proposed large number of electronic excitations and less charge loss at donor/acceptor interfaces due to small binding energy than reference molecule.
Graphic abstract
Charge transfer mechanism for adiabatic and vertical exchange.
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References
Abbas, M., Ali, U., Faizan, M., Siddique, M.B.A.: Spirofluorene based small molecules as an alternative to traditional non-fullerene acceptors for organic solar cells. Opt. Quant. Electron. 53, 1–14 (2021). https://doi.org/10.1007/s11082-020-02672-3
Ajmal, M., Ali, U., Javed, A., Tariq, A., Arif, Z., Iqbal, J., Ahmed, T.: Designing indaceno thiophene-based three new molecules containing non-fullerene acceptors as strong electron withdrawing groups with DFT approaches. J. Mol. Model. 25, 1–9 (2019). https://doi.org/10.1007/s00894-019-4198-x
Ali, U., Javed, A., Shoaib, M., Kashif, M., Raza, A., Cheng, S.B., Iqbal, J.: Designing difluoro substituted benzene ring based fullerene free acceptors for small naphthalene Di-Imide based molecules with DFT approaches. Opt. Quant. Electron. 51, 1–23 (2019). https://doi.org/10.1007/s11082-019-2047-x
Ali, U., Ans, M., Iqbal, J., Iqbal, M.A., Shoaibm, M.: Benchmark study of benzamide derivatives and four novel theoretically designed (L1, L2, L3, and L4) ligands and evaluation of their biological properties by DFT approaches. J. Mol. Model. 25, 1–9 (2019a). https://doi.org/10.1007/s00894-019-4115-3
Ali, U., Javed, A., Tallat, A., Iqbal, J., Raza, A.: Molecular designing of four high performance pyrazine-based non-fullerene acceptor materials with naphthalene diimide-based small organic solar cells. J. Mol. Model. 25, 1–12 (2019b). https://doi.org/10.1007/s00894-019-3932-8
Ali, U., Javed, A., Ramzan, H., Shoaib, M., Raza, A., Khalil, M.T., Cheng, S.B., Iqbal, J.: Molecular designing of naphthalene diimide based fullerene-free small organic solar cell—acceptors with high photovoltaic performance by density functional theory. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 228, 117685 (2020). https://doi.org/10.1016/j.saa.2019.117685
Ali, U., Tariq, A., Kiran, A., Abbas, F., Khalil, M.T.: Tuning the absorption and optoelectronic properties of naphthalene diimide based solar cells with non-fullerene acceptors. Chem. Pap. 8, 1–10 (2021). https://doi.org/10.1007/s11696-021-01671-2
Baran, D., Kirchartz, T., Wheeler, S., Dimitrov, S., Abdelsamie, M., Gorman, J., Ashraf, R.S., Holliday, S., Wadsworth, A., Gasparini, N.: Reduced voltage losses yield 10% efficient fullerene free organic solar cells with> 1 V open circuit voltages. Energy Environ. Sci. 9, 3783–3793 (2016). https://doi.org/10.1039/C6EE02598F
Barber, J.: Photosynthetic energy conversion: natural and artificial’. Chem. Soc. Rev. 38, 185–196 (2009). https://doi.org/10.1039/B802262N
Beheshtian, J., Peyghan, A.A., Bagheri, Z.: Theoretical investigation of C60 fullerene functionalization with tetrazine. Comput. Theor. Chem. 992, 164–167 (2012). https://doi.org/10.1016/j.comptc.2012.05.039
Chow, J., Kopp, R.J., Portney, P.R.: Energy resources and global development. Science 302, 1528–1531 (2003). https://doi.org/10.1126/science.1091939
Demirbaş, A.: Biomass resource facilities and biomass conversion processing for fuels and chemicals’. Energy Convers. Manag. 42, 1357–1378 (2001). https://doi.org/10.1016/S0196-8904(00)00137-0
Ellabban, O., Abu-Rub, H., Blaabjerg, F.: Renewable energy resources: current status, future prospects and their enabling technology. Renew. Sustain. Energy Rev. 39, 748–764 (2014). https://doi.org/10.1016/j.rser.2014.07.113
Garcia-Belmonte, G., Boix, P.P., Bisquert, J., Sessolo, M., Bolink, H.J.: Simultaneous determination of carrier lifetime and electron density-of-states in P3HT: PCBM organic solar cells under illumination by impedance spectroscopy. Solar Energy Mater. Sol. Cells 94, 366–375 (2010). https://doi.org/10.1016/j.solmat.2009.10.015
Goetzberger, A., Hebling, C.: Photovoltaic materials, past, present, future. Sol. Energy Mater. Sol. Cells 62, 1–19 (2000). https://doi.org/10.1016/S0927-0248(99)00131-2
Haije, W., Geerlings, H.: Efficient Production of Solar Fuel Using Existing large Scale Production Technologies. ACS Publications, New York (2011)
Hoppe, H., Sariciftci, N.S.: Organic solar cells: an overview. J. Mater. Res. 19, 1924–1945 (2004). https://doi.org/10.1557/JMR.2004.0252
Hussain, Z., Shoaib, M., Ali, U., Ramzan, H., Ali, M., Tariq, A., Naqash, M.: Theoretical study of isoxazoles and their derivatives for evaluating its pharmaceutical properties with density functional theory. J. Comput. Chem. Mol. Model. 4, 415–426 (2020). https://doi.org/10.25177/JCCMM.4.3.RA.10623
Iftikhar, T., Ali, U., Shoaib, M.: Theoretical study of α, β unsaturated carbonyl thiophene derivatives to investigate optoelectronic properties toward organic photovoltaics. J. Mol. Model. 26, 1–8 (2020). https://doi.org/10.1007/s00894-020-04597-w
Kongkanand, A., Domínguez, R.M., Kamat, P.V.: Single wall carbon nanotube scaffolds for photoelectrochemical solar cells. Capture and transport of photogenerated electrons. Nano Lett. 7, 676–680 (2007). https://doi.org/10.1021/nl0627238
Lewis, N.S., Nocera, D.G.: Powering the planet: chemical challenges in solar energy utilization. Proc. Natl. Acad. Sci. 103, 15729–15735 (2006). https://doi.org/10.1073/pnas.0603395103
Li, Y.: Molecular design of photovoltaic materials for polymer solar cells: toward suitable electronic energy levels and broad absorption. Acc. Chem. Res. 45, 723–733 (2012). https://doi.org/10.1021/ar2002446
Li, G., Zhu, R., Yang, Y.: Polymer solar cells. Nat. Photon. 6, 153–161 (2012). https://doi.org/10.1038/nphoton.2012.11
Lin, Y., Zhang, Z.G., Bai, H., Wang, J., Yao, Y., Li, Y., Zhu, D., Zhan, X.: High-performance fullerene-free polymer solar cells with 6.31% efficiency. Energy Environ. Sci. 8, 610–616 (2015). https://doi.org/10.1039/C4EE03424D
Liska, P., Thampi, K.R., Grätzel, M., Bremaud, D., Rudmann, D., Upadhyaya, H.M., Tiwari, A.N.: Nanocrystalline dye-sensitized solar cell/copper indium gallium selenide thin-film tandem showing greater than 15% conversion efficiency. Appl. Phys. Lett. 88, 203103 (2006). https://doi.org/10.1063/1.2203965
Liu, Y., Zhao, J., Li, Z., Mu, C., Ma, W., Hu, H., Jiang, K., Lin, H., Ade, H., Yan, H.: Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells. Nat. Commun. 5, 1–8 (2014). https://doi.org/10.1038/ncomms6293
Luque, A., Hegedus, S.: Handbook of Photovoltaic Science and Engineering. Wiley, New York (2011). https://doi.org/10.1002/9780470974704
Mutolo, K.L., Mayo, E.I., Rand, B.P., Forrest, S.R., Thompson, M.E.: Enhanced open-circuit voltage in subphthalocyanine/C60 organic photovoltaic cells. J. Am. Chem. Soc. 128, 8108–8109 (2006). https://doi.org/10.1021/ja061655o
Naghavi, N., Spiering, S., Powalla, M., Cavana, B., Lincot, D.: High-efficiency copper indium gallium diselenide (CIGS) solar cells with indium sulfide buffer layers deposited by atomic layer chemical vapor deposition (ALCVD). Progress Photovolt. Res. Appl. 11, 437–443 (2003). https://doi.org/10.1002/PIP.508
Potscavage, W.J., Sharma, A., Kippelen, B.: Critical interfaces in organic solar cells and their influence on the open-circuit voltage. Acc. Chem. Res. 42, 1758–1767 (2009). https://doi.org/10.1021/ar900139v
Scharber, M.C., Mühlbacher, D., Koppe, M., Denk, P., Waldauf, C., Heeger, A.J., Brabec, C.J.: Design rules for donors in bulk-heterojunction solar cells—towards 10% energy-conversion efficiency. Adv. Mater. 18, 789–794 (2006). https://doi.org/10.1002/adma.201504914
Sung, M.J., Huang, M., Moon, S.H., Lee, T.H., Park, S.Y., Kim, J.Y., Kwon, S.K., Choi, H., Kim, Y.H.: Naphthalene diimide-based small molecule acceptors for fullerene-free organic solar cells. Sol. Energy 150, 90–95 (2017). https://doi.org/10.1016/j.solener.2017.03.090
Tritt, T.M., Böttner, H., Chen, L.: Thermoelectrics: direct solar thermal energy conversion. MRS Bull. 33, 366–368 (2008). https://doi.org/10.1557/mrs2008.73
Winder, C., Sariciftci, N.S.: Low bandgap polymers for photon harvesting in bulk heterojunction solar cells. J. Mater. Chem. 14, 1077–1086 (2004). https://doi.org/10.1039/B306630D
Wöhrle, D., Meissner, D.: Organic solar cells. Adv. Mater. 3, 129–138 (1991). https://doi.org/10.1002/adma.19910030303
Zhao, J., Wang, A., Green, M.A., Ferrazza, F.: 19.8% efficient “honeycomb” textured multicrystalline and 24.4% monocrystalline silicon solar cells. Appl. Phys. Lett. 73, 1991–1993 (1998). https://doi.org/10.1063/1.122345
Zhou, H., Yang, L., Stuart, A.C., Price, S.C., Liu, S., You, W.: Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7% efficiency. Angew. Chem. 123, 3051–3054 (2011). https://doi.org/10.1002/anie.201005451
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The authors acknowledge the resources provided for this computational study to Punjab Bio-Energy Institute (PBI), Jhang road, Faisalabad and Chemistry department, University of Agriculture, Faisalabad, Pakistan.
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Ali, U., Ahmad, H.M.R., Faizan, M. et al. Designing four naphthalene di-imide based small organic solar cells with 5,6-difluoro-3-oxo-2,3-dihydro-indene non-fullerene acceptors. Opt Quant Electron 53, 541 (2021). https://doi.org/10.1007/s11082-021-03209-y
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DOI: https://doi.org/10.1007/s11082-021-03209-y