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Year 2023, , 296 - 301, 30.06.2023

Mustafa Elik

https://doi.org/10.17776/csj.1252908

Abstract

Keywords

compounds with rich π-electrons reorganization energies Marcus theory charge transfer rate.

References

  • [1] [Tendongmo H., et al., Theoretical Study of the Structural, Optoelectronic, and Reactivity Properties of N-[5 '-Methyl-3 '-Isoxasolyl]-N-[(E)-1-(-2-)]Methylidene] Amine and Some of Its Fe2+, Co2+, Ni2+, Cu2+, and Zn2+ Complexes for OLED and OFET Applications, Journal of Chemistry, (2022).
  • [2] Lougdali M., et al., Photoluminescence and nonlinear optical properties of Nickel bis-(8-hydroxyquinoline) thin film, Materials Chemistry and Physics, (2022) 284.
  • [3] Hebbali, R., Mekelleche S.M., Zaitri L.K., Computational study of optoelectronic properties of oxadiazole-based compounds for organic light emitting diodes, Molecular Physics, 120(14) (2022).
  • [4] Youssef A.A., et al., Designing Donor-Acceptor thienopyrazine derivatives for more efficient organic photovoltaic solar cell: A DFT study, Physica B-Condensed Matter, 560 (2019) 111-125.
  • [5] Omidyan R., Abbasi M. and Azimi G., Photophysical and optoelectronic properties of a platinum(II) complex and its derivatives, designed as a highly efficient OLED emitter: A theoretical study, International Journal of Quantum Chemistry, 119(3) (2019).
  • [6] Qin X., Dong H.L., and Hu W.P., Phthalocyanine-based organic semiconductors catalyzed C-H activation for heteroarenes functional materials in the sunlight, Chinese Science Bulletin-Chinese., 65(5) (2020) 417-424.
  • [7] Ho P.Y., et al., Synthesis and characterization of a semiconducting and solution-processable ruthenium-based polymetallayne, Polymer Chemistry, 11(2) (2020) 472-479.
  • [8] Ochsenbein S.T., et al., Engineering Color-Stable Blue Light-Emitting Diodes with Lead Halide Perovskite Nanocrystals, Acs Applied Materials & Interfaces., 11(24) (2019) 21655-21660.
  • [9] He Z.F., et al., High-Efficiency Red Light-Emitting Diodes Based on Multiple Quantum Wells of Phenylbutylammonium-Cesium Lead Iodide Perovskites, Acs Photonics., 6(3) (2019) 587-594.
  • [10] Chauhan A.K., et al., Organic Devices: Fabrication, Applications and Challenge, Journal of Electronic Materials, 51(2) (2022) 447-485.
  • [11] Park J.W., Shin D.C., and Park S.H., Large-area OLED lightings and their applications, Semiconductor Science and Technology, 26(3) (2011).
  • [12] Liu N., et al., Effects of Charge Transport Materials on Blue Fluorescent Organic Light-Emitting Diodes with a Host-Dopant System, Micromachines, 10(5) (2019).
  • [13] Predeep P., et al., Organic Light Emitting Diodes: Effect of Annealing the Hole Injection Layer on the Electrical and Optical Properties, Latest Trends in Condensed Matter Physics: Experimental and Theoretical Aspects, 171 (2011) 39-50.
  • [14] Choudhary R.B., and Kandulna R., 2-D rGO impregnated circular-tetragonal-bipyramidal structure of PPY-TiO2-rGO nanocomposite as ETL for OLED and supercapacitor electrode materials, Materials Science in Semiconductor Processing, 94 (2019) 86-96.
  • [15] Liu Y.C., et al., All-organic thermally activated delayed fluorescence materials for organic light-emitting diodes, Nature Reviews Materials, 3(4) (2018).
  • [16] Kim J.H., Triambulo R.E., and Park J.W., Effects of the interfacial charge injection properties of silver nanowire transparent conductive electrodes on the performance of organic light-emitting diodes, Journal of Applied Physics, 121(10) (2017).
  • [17] Siddiqui Q.T., et al., Thermally Activated Delayed Fluorescence (Green) in Undoped Film and Exciplex Emission (Blue) in Acridone-Carbazole Derivatives for OLEDs, Journal of Physical Chemistry C., 123(2) (2019) 1003-1014.
  • [18] Guo J.J., Zhao Z.J., and Tang B.Z., Purely Organic Materials with Aggregation-Induced Delayed Fluorescence for Efficient Nondoped OLEDs, Advanced Optical Materials, 6(15) (2018).
  • [19] Zajac D., et al., Conjugated silane-based arylenes as luminescent materials, Electrochimica Acta, 173 (2015) 105-116.
  • [20] Martin C., et al., Bipolar luminescent azaindole derivative exhibiting aggregation-induced emission for non-doped organic light-emitting diodes, Journal of Materials Chemistry C., 7(5) (2019) 1222-1227.
  • [21] Chakraborty A., et al., [8] Cyclo-1, 4-naphthylene: A possible new member in hole transport family, Chemical Physics Letters., 715 (2019) 153-159.
  • [22] Sutradhar T., and Misra A., Role of Electron-Donating and Electron-Withdrawing Groups in Tuning the Optoelectronic Properties of Difluoroboron-Napthyridine Analogues, Journal of Physical Chemistry A., 122(16) (2018) 4111-4120.
  • [23] Surukonti N., and Kotamarthi B., Mono substituted pyrenes as multifunctional materials for OLED: Analysis of the substituent effects on the charge transport properties using DFT methods, Computational and Theoretical Chemistry, 1138 (2018) 48-56.
  • [24] Frisch M.J., et al., Gaussian 16 Rev. B.01., (2016) Wallingford, CT.
  • [25] Dennington R., Keith T.A., and Millam J.M., GaussView, Version 6., (2016) Semichem Inc.: Shawnee Mission, KS.
  • [26] te Velde G., et al., Chemistry with ADF., Journal of Computational Chemistry., 22(9) (2001) 931-967.
  • [27] Servan S.A., et al., Assessment of the Density-Fitted Second-Order Quasidegenerate Perturbation Theory for Transition Energies: Accurate Computations of Singlet-Triplet Gaps for Charge-Transfer Compounds, J. Phys Chem A., 124(34) (2020) 6889-6898.
  • [28] Samsonova L.G., et al., Experimental and theoretical study of photo- and electroluminescence of divinyldiphenyl and divinylphenanthrene derivatives, Spectrochim Acta A Mol Biomol Spectrosc., 173 (2017) 59-64.
  • [29] Marcus R.A., Electron-Transfer Reactions in Chemistry - Theory and Experiment, Reviews of Modern Physics, 65(3) (1993) 599-610.
  • [30] Marcus R., Annu., Rev. Phys. Chem., (1964).
  • [31] Hush N.S., Adiabatic Rate Processes at Electrodes, I. Energy‐Charge Relationships, The Journal of Chemical Physics, 28 (1958) 962-972.
  • [32] Chakraborty D., and Chattaraj P.K., Conceptual density functional theory based electronic structure principles, Chemical Science, 12(18) (2021) 6264-6279.
  • [33] Islam N. and Kaya S., Conceptual density functional theory and its application in the chemical domain, CRC Press., (2018).
  • [34] Ho T.L., Hard soft acids bases (HSAB) principle and organic chemistry, Chemical Reviews, 75(1) (1975) 1-20.
  • [35] Kaya S. and Kaya C., A new method for calculation of molecular hardness: a theoretical study, Computational and Theoretical Chemistry, 1060 (2015) 66-70.
  • [36] Kaya S. and Kaya C., A new equation for calculation of chemical hardness of groups and molecules, Molecular Physics, 113(11) (2015) 1311-1319.
  • [37] Ghanty, T.K. and Ghosh S.K., Correlation between hardness, polarizability, and size of atoms, molecules, and clusters, The Journal of Physical Chemistry, 97(19) (1993) 4951-4953.
  • [38] Chattaraj P. and Sengupta S., Popular electronic structure principles in a dynamical context, The Journal of Physical Chemistry, 100(40) (1996) 16126-16130.
  • [39] von Szentpály, L., Kaya S. and Karakuş N., Why and when is electrophilicity minimized, New theorems and guiding rules, The Journal of Physical Chemistry A., 124(51) (2020) 10897-10908.
  • [40] Wang Y.G., et al., The reactivity of ambident nucleophiles: Marcus theory or hard and soft acids and bases principle, Journal of Computational Chemistry, 40(31) (2019) 2761-2777.

Chemical Reactivities and Organic Light-emitting Diode Properties of some Polyaromatic Molecules

Year 2023, , 296 - 301, 30.06.2023

Mustafa Elik

https://doi.org/10.17776/csj.1252908

Abstract

High-performance organic-light emitting diode (OLED) display panels have been very popular lately due to their many advantages compared to liquid-crystal display (LCD) and light-emitting diode (LED) panels. It is also well known that the materials used in OLED panels are important in determining OLED performance. Starting with the selection of materials which have rich π-electrons will be a good start for the design of high-performance OLED materials. For this aim, the OLED properties of some cyclic aromatic structures with rich π-electrons such as 2,2ꞌ-bi-1,6-naphthyridine (BNP), 1,6-bis(4ꞌ-pyridine)-2,5-diazahexane (BPDH), 3,3ꞌ-bis[3-(2-pyridyl)pyrazol-1-yl]biphenyl (BPPB), 5,5ꞌ-dicyano-2,2ꞌ-bipyridine (DCBP), 2,2ꞌ-dimethyl-4,4ꞌ-bipyrimidine (DMBP), and 4ꞌ-phenyl-2,2ꞌ:6ꞌ2ꞌꞌterpyridine (Ph-TERPY) were theoretically analyzed using computational chemistry tools. The calculations of monomeric and dimeric structures of mentioned molecules were carried out at B3LYP/6-31G(d) and B3LYP/TZP levels, respectively. The OLED properties of the investigated compound were explained by means of OLED parameters such as the reorganization energies, adiabatic-vertical ionization potentials and adiabatic-vertical electron affinities, the effective transfer integrals, and the charge transfer ratios. In the light of computational chemistry, it is indicated that these studied molecules will be utilized in which layers of OLED device. In addition to OLED analysis, in the light of the calculated reactivity descriptors, the chemical reactivities of the studied molecules were discussed.

Keywords

Compounds with rich π-electrons Reorganization energies Marcus theory Charge transfer rate

References

  • [1] [Tendongmo H., et al., Theoretical Study of the Structural, Optoelectronic, and Reactivity Properties of N-[5 '-Methyl-3 '-Isoxasolyl]-N-[(E)-1-(-2-)]Methylidene] Amine and Some of Its Fe2+, Co2+, Ni2+, Cu2+, and Zn2+ Complexes for OLED and OFET Applications, Journal of Chemistry, (2022).
  • [2] Lougdali M., et al., Photoluminescence and nonlinear optical properties of Nickel bis-(8-hydroxyquinoline) thin film, Materials Chemistry and Physics, (2022) 284.
  • [3] Hebbali, R., Mekelleche S.M., Zaitri L.K., Computational study of optoelectronic properties of oxadiazole-based compounds for organic light emitting diodes, Molecular Physics, 120(14) (2022).
  • [4] Youssef A.A., et al., Designing Donor-Acceptor thienopyrazine derivatives for more efficient organic photovoltaic solar cell: A DFT study, Physica B-Condensed Matter, 560 (2019) 111-125.
  • [5] Omidyan R., Abbasi M. and Azimi G., Photophysical and optoelectronic properties of a platinum(II) complex and its derivatives, designed as a highly efficient OLED emitter: A theoretical study, International Journal of Quantum Chemistry, 119(3) (2019).
  • [6] Qin X., Dong H.L., and Hu W.P., Phthalocyanine-based organic semiconductors catalyzed C-H activation for heteroarenes functional materials in the sunlight, Chinese Science Bulletin-Chinese., 65(5) (2020) 417-424.
  • [7] Ho P.Y., et al., Synthesis and characterization of a semiconducting and solution-processable ruthenium-based polymetallayne, Polymer Chemistry, 11(2) (2020) 472-479.
  • [8] Ochsenbein S.T., et al., Engineering Color-Stable Blue Light-Emitting Diodes with Lead Halide Perovskite Nanocrystals, Acs Applied Materials & Interfaces., 11(24) (2019) 21655-21660.
  • [9] He Z.F., et al., High-Efficiency Red Light-Emitting Diodes Based on Multiple Quantum Wells of Phenylbutylammonium-Cesium Lead Iodide Perovskites, Acs Photonics., 6(3) (2019) 587-594.
  • [10] Chauhan A.K., et al., Organic Devices: Fabrication, Applications and Challenge, Journal of Electronic Materials, 51(2) (2022) 447-485.
  • [11] Park J.W., Shin D.C., and Park S.H., Large-area OLED lightings and their applications, Semiconductor Science and Technology, 26(3) (2011).
  • [12] Liu N., et al., Effects of Charge Transport Materials on Blue Fluorescent Organic Light-Emitting Diodes with a Host-Dopant System, Micromachines, 10(5) (2019).
  • [13] Predeep P., et al., Organic Light Emitting Diodes: Effect of Annealing the Hole Injection Layer on the Electrical and Optical Properties, Latest Trends in Condensed Matter Physics: Experimental and Theoretical Aspects, 171 (2011) 39-50.
  • [14] Choudhary R.B., and Kandulna R., 2-D rGO impregnated circular-tetragonal-bipyramidal structure of PPY-TiO2-rGO nanocomposite as ETL for OLED and supercapacitor electrode materials, Materials Science in Semiconductor Processing, 94 (2019) 86-96.
  • [15] Liu Y.C., et al., All-organic thermally activated delayed fluorescence materials for organic light-emitting diodes, Nature Reviews Materials, 3(4) (2018).
  • [16] Kim J.H., Triambulo R.E., and Park J.W., Effects of the interfacial charge injection properties of silver nanowire transparent conductive electrodes on the performance of organic light-emitting diodes, Journal of Applied Physics, 121(10) (2017).
  • [17] Siddiqui Q.T., et al., Thermally Activated Delayed Fluorescence (Green) in Undoped Film and Exciplex Emission (Blue) in Acridone-Carbazole Derivatives for OLEDs, Journal of Physical Chemistry C., 123(2) (2019) 1003-1014.
  • [18] Guo J.J., Zhao Z.J., and Tang B.Z., Purely Organic Materials with Aggregation-Induced Delayed Fluorescence for Efficient Nondoped OLEDs, Advanced Optical Materials, 6(15) (2018).
  • [19] Zajac D., et al., Conjugated silane-based arylenes as luminescent materials, Electrochimica Acta, 173 (2015) 105-116.
  • [20] Martin C., et al., Bipolar luminescent azaindole derivative exhibiting aggregation-induced emission for non-doped organic light-emitting diodes, Journal of Materials Chemistry C., 7(5) (2019) 1222-1227.
  • [21] Chakraborty A., et al., [8] Cyclo-1, 4-naphthylene: A possible new member in hole transport family, Chemical Physics Letters., 715 (2019) 153-159.
  • [22] Sutradhar T., and Misra A., Role of Electron-Donating and Electron-Withdrawing Groups in Tuning the Optoelectronic Properties of Difluoroboron-Napthyridine Analogues, Journal of Physical Chemistry A., 122(16) (2018) 4111-4120.
  • [23] Surukonti N., and Kotamarthi B., Mono substituted pyrenes as multifunctional materials for OLED: Analysis of the substituent effects on the charge transport properties using DFT methods, Computational and Theoretical Chemistry, 1138 (2018) 48-56.
  • [24] Frisch M.J., et al., Gaussian 16 Rev. B.01., (2016) Wallingford, CT.
  • [25] Dennington R., Keith T.A., and Millam J.M., GaussView, Version 6., (2016) Semichem Inc.: Shawnee Mission, KS.
  • [26] te Velde G., et al., Chemistry with ADF., Journal of Computational Chemistry., 22(9) (2001) 931-967.
  • [27] Servan S.A., et al., Assessment of the Density-Fitted Second-Order Quasidegenerate Perturbation Theory for Transition Energies: Accurate Computations of Singlet-Triplet Gaps for Charge-Transfer Compounds, J. Phys Chem A., 124(34) (2020) 6889-6898.
  • [28] Samsonova L.G., et al., Experimental and theoretical study of photo- and electroluminescence of divinyldiphenyl and divinylphenanthrene derivatives, Spectrochim Acta A Mol Biomol Spectrosc., 173 (2017) 59-64.
  • [29] Marcus R.A., Electron-Transfer Reactions in Chemistry - Theory and Experiment, Reviews of Modern Physics, 65(3) (1993) 599-610.
  • [30] Marcus R., Annu., Rev. Phys. Chem., (1964).
  • [31] Hush N.S., Adiabatic Rate Processes at Electrodes, I. Energy‐Charge Relationships, The Journal of Chemical Physics, 28 (1958) 962-972.
  • [32] Chakraborty D., and Chattaraj P.K., Conceptual density functional theory based electronic structure principles, Chemical Science, 12(18) (2021) 6264-6279.
  • [33] Islam N. and Kaya S., Conceptual density functional theory and its application in the chemical domain, CRC Press., (2018).
  • [34] Ho T.L., Hard soft acids bases (HSAB) principle and organic chemistry, Chemical Reviews, 75(1) (1975) 1-20.
  • [35] Kaya S. and Kaya C., A new method for calculation of molecular hardness: a theoretical study, Computational and Theoretical Chemistry, 1060 (2015) 66-70.
  • [36] Kaya S. and Kaya C., A new equation for calculation of chemical hardness of groups and molecules, Molecular Physics, 113(11) (2015) 1311-1319.
  • [37] Ghanty, T.K. and Ghosh S.K., Correlation between hardness, polarizability, and size of atoms, molecules, and clusters, The Journal of Physical Chemistry, 97(19) (1993) 4951-4953.
  • [38] Chattaraj P. and Sengupta S., Popular electronic structure principles in a dynamical context, The Journal of Physical Chemistry, 100(40) (1996) 16126-16130.
  • [39] von Szentpály, L., Kaya S. and Karakuş N., Why and when is electrophilicity minimized, New theorems and guiding rules, The Journal of Physical Chemistry A., 124(51) (2020) 10897-10908.
  • [40] Wang Y.G., et al., The reactivity of ambident nucleophiles: Marcus theory or hard and soft acids and bases principle, Journal of Computational Chemistry, 40(31) (2019) 2761-2777.
There are 40 citations in total.

Details

Primary Language English
Subjects Physical Organic Chemistry
Journal Section Natural Sciences
Authors

Mustafa Elik 0000-0001-8245-4273

Publication Date June 30, 2023
Submission Date February 18, 2023
Acceptance Date June 9, 2023
Published in Issue Year 2023

Cite

APA Elik, M. (2023). Chemical Reactivities and Organic Light-emitting Diode Properties of some Polyaromatic Molecules. Cumhuriyet Science Journal, 44(2), 296-301. https://doi.org/10.17776/csj.1252908