Symmetrical and asymmetrical imino-naphthalimides in perovskite solar cells

• Autorzy: Korzec Mateusz , Kotowicz Sonia , Pająk Agnieszka Katarzyna , Schab-Balcerzak Ewa

Identyfikatory

DOI

10.24425/opelre.2021.139755

• Języki publikacji: EN

Abstrakty

EN

In perovskite solar cells, series of symmetrical and asymmetrical imino-naphthalimides were tested as hole-transporting materials. The compounds exhibited high thermal stability at the temperature of the beginning of thermal decomposition above 300 °C. Obtained imino-naphthalimides were electrochemically active and their adequate energy levels confirm the application possibility in the perovskite solar cells. Imino-naphthalimides were absorbed with the maximum wavelength in the range from 331 nm to 411 nm and emitted light from the blue spectral region in a chloroform solution. The presented materials were tested in the perovskite solar cells devices with a construction of FTO/b-TiO2/m-TiO2/perovskite/ HTM/Au. For comparison, the reference perovskite cells were also performed (without hole-transporting materials layer). Of all the proposed materials tested as hole-transporting materials, the bis-(imino-naphthalimide) containing in core the triphenylamine structure showed a power conversion efficiency at 1.10% with a short-circuit current at 1.86 mA and an open-circuit voltage at 581 mV.

Słowa kluczowe

EN

naphthalimide; perovskite solar cell; Schiff base; imine

• Wydawca: Stowarzyszenie Elektryków Polskich ; Polska Akademia Nauk ; Wojskowa Akademia Techniczna im. Jarosława Dąbrowskiego
• Czasopismo: Opto-Electronics Review
• Rocznik: 2021
• Tom: Vol. 29, No. 4
• Strony: 175--180
• Opis fizyczny: Bibliogr. 40 poz., tab., wykr.

Twórcy

autor

Korzec Mateusz

• Institute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, 9 Szkolna St., 40-007 Katowice, Poland

• https://orcid.org/https%3A//orcid.org/0000-0002-8658-1031

autor

Kotowicz Sonia

• Institute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, 9 Szkolna St., 40-007 Katowice, Poland

• https://orcid.org/https%3A//orcid.org/0000-0001-6021-0892

autor

Pająk Agnieszka Katarzyna

• Institute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, 9 Szkolna St., 40-007 Katowice, Poland
• Institute of Metallurgy and Materials Science, Polish Academy of Sciences, 25 Reymont St., 30-059 Krakow, Poland

• https://orcid.org/https%3A//orcid.org/0000-0002-2684-4629

autor

Schab-Balcerzak Ewa

• Institute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, 9 Szkolna St., 40-007 Katowice, Poland
• Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Skłodowska St., 41-819 Zabrze, Poland

• https://orcid.org/https%3A//orcid.org/0000-0002-7219-8664

Bibliografia

• [1] Gopikrishna, P., Meher, N. & Iyer P. K. Functional 1,8-naphthalimide AIE/AIEEgens: recent advances and prospects. ACS Appl. Mater. Interfaces 10, 12081–12111 (2018). https://doi.org/10.1021/acsami.7b14473
• [2] Banerjee, S. et al. Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents. Chem. Soc. Rev. 42, 1601–1618 (2013). https://doi.org/10.1039/C2CS35467E
• [3] Poddar, M., Sivakumar, G. & Misra, R. Donor-acceptor substituted 1,8-naphthalimides: design, synthesis, and structure–property relationship J. Mater. Chem. C 7, 14798–14815 (2019). https://doi.org/10.1039/C9TC02634G
• [4] Tomczyk, M. D. & Walczak K. Z. l,8-Naphthalimide based DNA intercalators and anticancer agents. A systematic review from 2007 to 2017. Eur. J. Med. Chem. 159, 393–422 (2018). https://doi.org/10.1016/j.ejmech.2018.09.055
• [5] Gan, J.-A. et al. 1,8-naphthalimides for non-doping OLEDs: the tunable emission color from blue, green to red. J. Photochem. Photobiol. 162, 399–406 (2004). https://doi.org/10.1016/S1010-6030(03)00381-2
• [6] Luo, S. et al. Novel 1,8-naphthalimide derivatives for standard-red organic light-emitting device applications. J. Mater. Chem. C 3, 525–5267 (2015). https://doi.org/10.1039/C5TC00409H
• [7] Zhang, X. et al. A 1,8-naphthalimide based small molecular acceptor for polymer solar cells with high open circuit voltage, J. Mater. Chem. C 3, 6979–6985 (2015). https://doi.org/10.1039/C5TC01148E
• [8] Do, T. T. et al. Molecular engineering strategy for high efficiency fullerene-free organic solar cells using conjugated 1,8-naphthal-imide and fluorenone building blocks. ACS Appl. Mater. Interfaces 9, 16967–16976 (2017). https://doi.org/10.1021/acsami.6b16395
• [9] Yadagiri, B. et al. An all-small-molecule organic solar cell derived from naphthalimide for solution-processed high-efficiency non-fullerene acceptors. J. Mater. Chem. C 7, 709–717 (2019). https://doi.org/10.1039/C8TC05692G
• [10] Torres-Moya, I. et al. Synthesis of D-π-A high-emissive 6-arylalkynyl-1,8-naphthalimides for application in organic field-effect transistors and optical waveguides Dyes and Pigm. 191, 109358 (2021). https://doi.org/10.1016/j.dyepig.2021.109358
• [11] Gudeika, D. A review of investigation on 4-substituted 1,8-naphthalimide derivatives. Synth. Met. 262, 116328 (2020). https://doi.org/10.1016/j.synthmet.2020.116328
• [12] Xie, L. et al. 5-Non-amino aromatic substituted naphthalimides as potential antitumor agents: Synthesis via Suzuki reaction, antiproliferative activity, and DNA-binding behavior. Bioorg. Med. Chem. 19, 961–967 (2011). https://doi.org/10.1016/j.bmc.2010.11.055
• [13] Rykowski, S. et al. Design, synthesis, and evaluation of novel 3-carboranyl-1,8-naphthalimide derivatives as potential anticancer agents. Int. J. Mol. Sci. 22, 2772 (2021). https://doi.org/10.3390/ijms22052772
• [14] Sivakumar, G. et al. Design, synthesis and characterization of 1,8-naphthalimide based fullerene derivative as electron transport material for inverted perovskite solar cells. Synth. Met. 249, 25–30 (2019). https://doi.org/10.1016/j.synthmet.2019.01.014
• [15] Li, L. et al. Self-assembled naphthalimide derivatives as an efficient and low-cost electron extraction layer for n-i-p perovskite solar cells. Chem. Commun. 55, 13239–13242 (2019). https://doi.org/10.1039/C9CC06345E
• [16] Agarwala, P. & Kabra, D. A review on triphenylamine (TPA) based organic hole transport materials (HTMs) for dye sensitized solar cells (DSSCs) and perovskite solar cells (PSCs): evolution and molecular engineering. J. Mater. Chem. A 5, 1348–1373 (2017). https://doi.org/10.1039/C6TA08449D
• [17] Duan, L. et al. Facile synthesis of triphenylamine-based hole-transporting materials for planar perovskite solar cells. J. Power Sources 435, 226767 (2019). https://doi.org/10.1016/j.jpowsour.2019.226767
• [18] Wu, G. et al. Triphenylamine-based hole transporting materials with thiophene-derived bridges for perovskite solar cells. Synth. Met. 261, 116323 (2020). https://doi.org/10.1016/j.synthmet.2020.116323
• [19] Rezaei, F. & Mohajeri, A. Molecular designing of triphenylamine-based hole-transporting materials for perovskite solar cells Sol. Energy 221, 536–544 (2021). https://doi.org/10.1016/j.solener.2021.04.055
• [20] Li, M. et al. Facile donor (D)-π-D triphenylamine-based hole transporting materials with different π-linker for perovskite solar cells. Sol. Energy 195, 618–625 (2020). https://doi.org/10.1016/j.solener.2019.11.071
• [21] Bogdanowicz, K. A. et al. Selected electrochemical properties of 4,4’-((1E,1’E)-((1,2,4-Thiadiazole-3,5-diyl)bis(azaneylylidene))-bis(methaneylylidene))bis(N,N-di-p-tolylaniline) towards perovskite solar cells with 14.4% efficiency. Materials 13, 2440 (2020). https://doi.org/10.3390/ma13112440
• [22] Ma, B.-B. et al. Visualized acid–base discoloration and optoelectronic investigations of azines and azomethines having double 4-[N,N-di(4-methoxyphenyl)amino]phenyl terminals. J. Mater. Chem. C 3, 7748–7755 (2015). https://doi.org/10.1039/C5TC00909J
• [23] Korzec, M. et al. Synthesis and thermal, photophysical, electrochemical properties of 3,3-di[3-arylcarbazol-9-ulmethyl]oxetane derivatives. Materials 14, 5569 (2021). https://doi.org/10.3390/ma14195569
• [24] Pająk, A. K. et al. New thiophene imines acting as hole transporting materials in photovoltaic devices. Energy Fuels 34, 10160–10169 (2020). https://doi.org/10.1021/acs.energyfuels.0c01698
• [25] Kula, S. et al. 9,9’-bifluorenylidene derivatives as novel hole-transporting materials for potential photovoltaic applications. Dyes Pigm. 174, 108031 (2020). https://doi.org/10.1016/j.dyepig.2019.108031
• [26] Derkowska-Zielinska, B. et al. Photovoltaic cells with various azo dyes as components of the active layer. Sol. Energy 203, 19–24 (2020). https://doi.org/10.1016/j.solener.2020.04.022
• [27] Nitschke, P. et al. Spectroscopic and electrochemical properties of thiophene-phenylene based Schiff-bases with alkoxy side groups, towards photovoltaic applications. Spectrochim. Acta A 248, 119242 (2021). https://doi.org/10.1016/j.saa.2020.119242
• [28] Sęk, D. et al. Polycyclic aromatic hydrocarbons connected with Schiff base linkers: Experimental and theoretical photophysical characterization and electrochemical properties Spectrochim. Acta A, 175, 168–176 (2017). https://doi.org/10.1016/j.saa.2016.12.029
• [29] Korzec, M. et al. Live cell imaging by 3-imino-(2-phenol)-1,8-naphthalimides: The effect of ex vivo hydrolysis. Spectrochim. Acta A 238, 118442 (2020). https://doi.org/10.1016/j.saa.2020.118442
• [30] Kotowicz, S. et al. Novel 1,8-naphthalimides substituted at 3-C position: Synthesis and evaluation of thermal, electrochemical and luminescent properties. Dyes Pigm. 158, 65–78 (2018). https://doi.org/10.1016/j.dyepig.2018.05.017
• [31] Korzec, M. et al. Novel b-ketoenamines versus azomethines for organic electronics: characterization of optical and electrochemical properties supported by theoretical studies. J Mater Sci, 55, 3812–3832 (2020). https://doi.org/10.1007/s10853-019-04210-3
• [32] Kotowicz, S. et al. New acceptor–donor–acceptor systems based on bis-(imino-1,8-naphthalimide). Materials 14, 2714 (2021). https://doi.org/10.3390/ma14112714
• [33] Costa, J. S. C. et al. Optical band gaps of organic semiconductor materials Opt. Mater. 58, 51–60 (2016). https://doi.org/10.1016/j.optmat.2016.03.041
• [34] Nitschke, P. et al. The effect of alkyl substitution of novel imines on their supramolecular organization, towards photovoltaic applications, Sol. Energy 221, 536–544. https://doi.org/10.1016/j.solener.2021.04.055
• [35] Misra, A. et al. Electrochemical and optical studies of conjugated polymers for three primary colours. Indian J. Pure Appl. Phys. 43, 921–925 (2005).
• [36] Kim, K. et al. Direct p-doping of Li-TFSI for efficient hole injection: Role of polaronic level in molecular doping. Appl. Surf. Sci. 480, 565–571 (2019). https://doi.org/10.1016/j.apsusc.2019.02.248
• [37] Singh, R. & Parashar, M. Origin of Hysteresis in Perovskite Solar Cells in Soft-Matter Thin Film Solar Cells: Physical Processes and Device Simulation (AIP Publishing, on-line) (New York, 2020). https://doi.org/10.1063/9780735422414_001
• [38] Li, B. et al. Insights into the hole transport properties of LiTFSI-doped spiro-OMeTAD films through impedance spectroscopy. J. Appl. Phys.128, 085501 (2020). https://doi.org/10.1063/5.0011868
• [39] Abate, A. et al. Lithium salts “redox active” p-type dopants for organic semiconductors and their impact in solid-state dye-sensitized solar cells. Phys. Chem. Chem. Phys., 15, 2572–2579 (2013). https://doi.org/10.1039/C2CP44397J
• [40] Wang, S., Yan, W. & Meng, Y. S., Spectrum-dependent spiro-OMeTAD oxidization mechanism in perovskite solar cells. Appl. Mater. Interfaces 7, 24791–24798 (2015). https://doi.org/10.1021/acsami.5b07703