How to search?
advanced search

Search results

Filters

  • Journals
  • Authors
  • Keywords
  • Date
  • Type

Search results

Number of results: 2
items per page: 25 50 75
Sort by:

Symmetrical and asymmetrical imino-naphthalimides in perovskite solar cells

Mateusz Korzec Sonia Kotowicz Agnieszka K. Pająk Ewa Schab-Balcerzak
Opto-Electronics Review | 2021 | 29 | 4 | 175-180 | DOI: 10.24425/opelre.2021.139755
Keywords naphthalimides perovskite solar cells Schiff base imine
Download PDF Download RIS Download Bibtex

Abstract

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.
Go to article

Bibliography

  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. 1,8-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-trans-porting 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
Go to article

Authors and Affiliations

Mateusz Korzec
1
ORCID: ORCID
Sonia Kotowicz
1
ORCID: ORCID
Agnieszka K. Pająk
1 2
ORCID: ORCID
Ewa Schab-Balcerzak
1 3
ORCID: ORCID
  1. Institute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, 9 Szkolna St., 40-007 Katowice, Poland
  2. Institute of Metallurgy and Materials Science, Polish Academy of Sciences, 25 Reymont St., 30-059 Krakow, Poland
  3. Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Skłodowska St., 41-819 Zabrze, Poland

Protection of hydroxy groups as trimethylsilyl ethers catalyzed by recyclable magnetically Schiff-base complexes of Ruthenium by using HMDS

Somayeh Mehdigholami Esmaeil Koohestanian
Chemical and Process Engineering: New Frontiers | 2024 | vol. 45 | No 1 | e52 | DOI: 10.24425/cpe.2023.147411
Keywords Salen Ru(OTf)2 protection Hydroxy compound Nanocatalyst Schiff base
Download PDF Download RIS Download Bibtex

Abstract

In this study, a stable and effective magnetically recoverable nanocatalyst was prepared by coating Fe 3O 4 nanoparticles with SiO 2, followed by functionalization with N-(2-aminoethyl)- 3-aminopropyltrimethoxysilane (AEPTMS) and produce Schiff base ligand to linkage Ru(OTf) 2 onto the surface. The nanocatalyst was characterized using various techniques such as FT-IR spectroscopy, SEM, TEM, and VSM to confirm its successful synthesis. The nanocatalyst was used for the trimethylsilylation of various alcohols (primary, secondary, and tertiary alcohols) using hexamethyldisilazane as a silylating agent in dichloromethane at room temperature. The reaction proceeded quickly with a protection time of only 90 seconds, which is a remarkable advantage of this nanocatalyst. The turnover frequency (TOF) values of the catalytic system were estimated to be 1869 h -1. The use of this nanocatalyst offers many advantages, such as excellent yield, catalyst reusability, high acidity, and strong magneticp roperties. These advantages make it a fascinating candidate for green chemistry principles. The simple reprocessing procedure and quick response times are also additional benefits of this nanocatalyst. Overall, this study provides a promising approach for the facile preparation of a stable and effective magnetically recoverable nanocatalyst that can be utilized for the trimethylsilylation of alcohols. The exceptional properties of this catalyst make it an attractive candidate for practical applications in the field of catalysis.
Go to article

Authors and Affiliations

Somayeh Mehdigholami
1
Esmaeil Koohestanian
2
  1. Young Researchers and Elite Club, Iranshahr Branch, Islamic Azad University, Iranshahr, Iran
  2. Department of Chemical Engineering, Iranshahr Branch, Islamic Azad University, Iranshahr, Iran

This page uses 'cookies'. Learn more