Optoelectronic Parameters of 2-oxo-2-(1-oxo-1H-isochromen-3-yl)ethyl methacrylate Compound Thin Film

Year 2022, Volume: 9 Issue: 2, 613 - 620, 31.05.2022

Adnan Kurt , Murat Koca

https://doi.org/10.18596/jotcsa.1028320

Abstract

The UV/VIS spectrophotometric scans were obtained to determine the opto-electronic properties of 2-oxo-2-(1-oxo-1H-isochromen-3-yl)ethyl methacrylate (other name: 2-(isocoumarin-3-yl)-2-oxoethyl methacrylate) compound thin film. The refractive index of compound at 700 nm was found to be 1.61. The values of the real part of the dielectric constant were higher than those of the imaginary part. The results indicated that the electronic transition responsible for the absorption was the indirect allowed one. The optical band gap constant and the Urbach energy corresponding to the width of the band tails of localized states were calculated to be 3.19 eV and 1.05 eV, respectively. From the results obtained, it is predicted that 2-oxo-2-(1-oxo-1H-isochromen-3-yl)ethyl methacrylate (OICEMA) compound can take place in the semiconductor class and play a role in the design of some electro-optic materials.

Keywords

1H-isochromen-1-one, isocoumarin, UV absorptions, optical properties, dispersion parameters

References

• 1. Han T, Deng H, Yu CYY, Gui C, Song Z, Kwok RTK, et al. Functional isocoumarin-containing polymers synthesized by rhodium-catalyzed oxidative polycoupling of aryl diacid and internal diyne. Polym Chem. 2016;7(14):2501–10.
• 2. Saeed A. Isocoumarins, miraculous natural products blessed with diverse pharmacological activities. European Journal of Medicinal Chemistry. 2016 Jun;116:290–317.
• 3. Saikia P, Gogoi S. Isocoumarins: General Aspects and Recent Advances in their Synthesis. Adv Synth Catal. 2018 Jun 5;360(11):2063–75.
• 4. Pal S, Chatare V, Pal M. Isocoumarin and Its Derivatives: An Overview on their Synthesis and Applications. COC. 2011 Mar 1;15(5):782–800.
• 5. Kurt A, Kılınç İ, Koca M. Preparation of Copolymer Systems of 2-(Isocoumarin-3-yl)-2-oxoethyl Methacrylate with Methyl Methacrylate and Thermal Decomposition Kinetics. Iran J Sci Technol Trans Sci. 2020 Aug;44(4):1039–50.
• 6. Koca M, Ertürk AS, Umaz A. Microwave-assisted intermolecular aldol condensation: Efficient one-step synthesis of 3-acetyl isocoumarin and optimization of different reaction conditions. Arabian Journal of Chemistry. 2018 May;11(4):538–45. 7. Barry RD. Isocoumarins. Developments since 1950. Chemical Reviews. 1964;64(3):229–60.
• 8. Tian JF, Li PJ, Li XX, Sun PH, Gao H, Liu XZ, et al. New antibacterial isocoumarin glycosides from a wetland soil derived fungal strain Metarhizium anisopliae. Bioorganic & Medicinal Chemistry Letters. 2016 Mar;26(5):1391–6.
• 9. Bai Y, Du J, Weng X. Synthesis, characterization, optical properties and theoretical calculations of 6-fluoro coumarin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014 May;126:14–20.
• 10. Kurt A, Gündüz B, Koca M. A detailed study on the optical properties of 3-benzoyl-7-hydroxy coumarin compound in different solvents and concentrations. Maced J Chem Chem Eng. 2019 Dec 30;38(2):227.
• 11. Karuk Elmas SN, Dincer ZE, Erturk AS, Bostanci A, Karagoz A, Koca M, et al. A novel fluorescent probe based on isocoumarin for Hg2+ and Fe3+ ions and its application in live-cell imaging. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2020 Jan;224:117402. <DOI> .
• 12. Pirovano V, Marchetti M, Carbonaro J, Brambilla E, Rossi E, Ronda L, et al. Synthesis and photophysical properties of isocoumarin-based D-π-A systems. Dyes and Pigments. 2020 Feb;173:107917.
• 13. Shoji T, Tanaka M, Takagaki S, Miura K, Ohta A, Sekiguchi R, et al. Synthesis of azulene-substituted benzofurans and isocoumarins via intramolecular cyclization of 1-ethynylazulenes, and their structural and optical properties. Org Biomol Chem. 2018;16(3):480–9.
• 14. Zamani K, Faghihi K, Ebrahimi S. Synthesis of Some Novel Optically Active Isocoumarin and 3,4-Dihydroisocoumarin Containing L-valine and L-leucine Moieties. Turk J Chem. 2005;29:171–5. .
• 15. Kurt A, Avci HI, Koca M. Synthesis and characterization of a novel isocoumarin derived polymer and its thermal decomposition kinetics. Maced J Chem Chem Eng [Internet]. 2018 Dec 3 [cited 2022 Apr 16];37(2).
• 16. Aziz SB, Brza MA, Nofal MM, Abdulwahid RT, Hussen SA, Hussein AM, et al. A Comprehensive Review on Optical Properties of Polymer Electrolytes and Composites. Materials. 2020 Aug 20;13(17):3675.
• 17. Rawat A, Mahawar H, Chauhan S, Tanwar A, Singh P. Optical band gap of polyvinylpyrrolidone/polyacrilamide blend thin films. IJPAP. 2012;50:100–4. .
• 18. Zidan HM, Abu-Elnader M. Structural and optical properties of pure PMMA and metal chloride-doped PMMA films. Physica B: Condensed Matter. 2005 Jan;355(1–4):308–17.
• 19. Atyia H. Influence of deposition temperature on the structural and optical properties of InSbSe~ 3 films. Journal of optoelectronics and advanced materials. 2006;8(4):1359.
• 20. Rodrı́guez J, Gómez M, Ederth J, Niklasson GA, Granqvist CG. Thickness dependence of the optical properties of sputter deposited Ti oxide films. Thin Solid Films. 2000 Apr;365(1):119–25.
• 21. Wemple SH, DiDomenico M. Behavior of the Electronic Dielectric Constant in Covalent and Ionic Materials. Phys Rev B. 1971 Feb 15;3(4):1338–51.
• 22. Veena G, Lobo B. Dispersive parameters of oxidized PVA-PVP blend films. Turkish Journal of Physics. 2019 Aug 1;43(4):337–54. .
• 23. Ammar AH. Studies on some structural and optical properties of ZnxCd1−xTe thin films. Applied Surface Science. 2002 Nov;201(1–4):9–19.
• 24. DrDomenico M, Wemple SH. Oxygen‐Octahedra Ferroelectrics. I. Theory of Electro‐optical and Nonlinear optical Effects. Journal of Applied Physics. 1969 Feb;40(2):720–34.
• 25. Tauc J, editor. Amorphous and Liquid Semiconductors. New York: Plenum Press; 1974.
• 26. Akshay VR, Arun B, Mandal G, Vasundhara M. Visible range optical absorption, Urbach energy estimation and paramagnetic response in Cr-doped TiO 2 nanocrystals derived by a sol–gel method. Phys Chem Chem Phys. 2019;21(24):12991–3004.
• 27. Urbach F. The Long-Wavelength Edge of Photographic Sensitivity and of the Electronic Absorption of Solids. Phys Rev. 1953 Dec 1;92(5):1324–1324.
• 28. Abu El-Fadl A, Soltan AS, Shaalan NM. Temperature dependence of the indirect band gap, steepness parameter and related optical constants of [Kx(NH4)1−x]2ZnCl4 mixed crystals. Optics & Laser Technology. 2007 Oct;39(7):1310–8.