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Synthesis and Optical Properties of 2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds

Year 2024, Volume: 7 Issue: 2, 208 - 214, 18.12.2024

Leyla Babali Özen , Furkan Özen , Bayram Gündüz , Günseli Turgut Cin

https://doi.org/10.54565/jphcfum.1583947

Abstract

The 2-(4-Trifluoromethylphenyl)-3-(4-methoxyphenyl) acrylonitrile (4MPAN-TFMP) compound was successfully synthesized and characterized using standard spectroscopic methods. Thin films of 4MPAN-TFMP were prepared by conventional spin-coating, with varying film thicknesses to investigate the thickness-dependent optical and photonic properties. UV-Vis spectra of the compounds in DMSO were recorded, and key parameters such as absorption (Abs), transmittance (T), absorption band edge (EAbs-be), optical band gap (Eg), and refractive index (n) were determined. The findings highlight the material’s potential for optoelectronic applications, as optimized film thicknesses can enhance material efficiency for various uses. This advancement offers promising implications for developing high-performance photonic devices and improving optoelectronic circuit components.

Keywords

Acrylonitriles Organic Semiconductors Photonic Properties Optoelectronic applications Film thickness.

Supporting Institution

TÜBİTAK and Akdeniz University

Project Number

TÜBİTAK, KBAG-119Z608 and AU-BAP, FBA-2020-5403 and FDK-2022-6056

Thanks

We would like to thank the Scientific and Technological Research Council of Turkey (TÜBİTAK, KBAG-119Z608) and Akdeniz University Scientific Research Projects Unit (AU-BAP, FBA-2020-5403 and FDK-2022-6056) for their financial support.

References

  • Roncali, J. (2011). Single material solar cells: the next frontier for organic photovoltaics. Advanced Energy Materials, 1(2), 147-160.
  • Wang, Y., Shang, H., Li, B., & Jiang, S. (2022). Reversible luminescence “off–on” regulation based on tunable photodimerization via crystal-to-cocrystal transformation. Journal of Materials Chemistry C, 10(2), 734-741.
  • Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A., & Puschmann, H. (2009). OLEX2: a complete structure solution, refinement and analysis program. Journal of applied crystallography, 42(2), 339-341.
  • Strieth-Kalthoff, F., James, M. J., Teders, M., Pitzer, L., & Glorius, F. (2018). Energy transfer catalysis mediated by visible light: principles, applications, directions. Chemical Society Reviews, 47(19), 7190-7202.
  • Zhou, Q. Q., Zou, Y. Q., Lu, L. Q., & Xiao, W. J. (2019). Visible‐light‐induced organic photochemical reactions through energy‐transfer pathways. Angewandte Chemie International Edition, 58(6), 1586-1604.
  • Gündüz, B. (2013). Effects of molarity and solvents on the optical properties of the solutions of tris [4-(5-dicyanomethylidenemethyl-2-thienyl) phenyl] amine (TDCV-TPA) and structural properties of its film. Optical Materials, 36(2), 425-436.
  • Lloyd, M. T., Anthony, J. E., & Malliaras, G. G. (2007). Photovoltaics from soluble small molecules. Materials Today, 10(11), 34-41.
  • Anandhan, K., Cerón, M., Perumal, V., Ceballos, P., Gordillo-Guerra, P., Pérez-Gutiérrez, E., ... & Percino, M. J. (2019). Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies. RSC advances, 9(21), 12085-12096.
  • Castillo, A., Ceballos, P., Santos, P., Cerón, M., Venkatesan, P., Pérez-Gutiérrez, E., ... & Percino, M. J. (2021). Solution and solid-state photophysical properties of positional Isomeric acrylonitrile derivatives with Core pyridine and phenyl moieties: experimental and DFT studies. Molecules, 26(6), 1500.
  • Jayabharathi, J., Thanikachalam, V., & Perumal, M. V. (2012). Physicochemical and solvatochromic analysis of an imidazole derivative as NLO material. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 85(1), 31-37.
  • Büchele, P., Richter, M., Tedde, S. F., Matt, G. J., Ankah, G. N., Fischer, R., ... & Schmidt, O. (2015). X-ray imaging with scintillator-sensitized hybrid organic photodetectors. Nature Photonics, 9(12), 843-848.
  • Hssain, A. H., Gündüz, B., Majid, A., & Bulut, N. (2021). NTCDA compounds of optoelectronic interest: Theoretical insights and experimental investigation. Chemical Physics Letters, 780, 138918.
  • Zhu, L., & Zhao, Y. (2013). Cyanostilbene-based intelligent organic optoelectronic materials. Journal of Materials Chemistry C, 1(6), 1059-1065.
  • Kim, M. J., An, T. K., Kim, S. O., Cha, H., Kim, H. N., Xiofeng, T., ... & Kim, Y. H. (2015). Molecular design and ordering effects of alkoxy aromatic donor in a DPP copolymer on OTFTs and OPVs. Materials Chemistry and Physics, 153, 63-71.
  • Fang, J. K., Sun, T., Tian, Y., Zhang, Y., Jin, C., Xu, Z., ... & Wang, H. (2017). Novel diyne-bridged dyes for efficient dye-sensitized solar cells. Materials Chemistry and Physics, 195, 1-9.
  • Shaikh, S. A., Mendhe, A. C., Nadimetla, D. N., Biradar, M. R., Vijayanand, P., Puyad, A. L., ... & Bhosale, S. V. (2024). Benzothiazole functionalized diketopyrrolopyrrole photosensitizer for CdS nanowire based DSSC applications. Journal of Photochemistry and Photobiology A: Chemistry, 447, 115220.
  • Sharma, G. D., Patel, K. R., Roy, M. S., & Misra, R. (2014). Characterization of two new (A–π) 2–D–A type dyes with different central D unit and their application for dye sensitized solar cells. Organic Electronics, 15(8), 1780-1790.
  • Jeong, H. G., Khim, D., Jung, E., Yun, J. M., Kim, J., Ku, J., ... & Kim, D. Y. (2013). Synthesis and characterization of a novel ambipolar polymer semiconductor based on a fumaronitrile core as an electron‐withdrawing group. Journal of Polymer Science Part A: Polymer Chemistry, 51(5), 1029-1039.
  • Gündüz, B. (2016). Investigation of the spectral, optical and surface morphology properties of the N, N′‐Dipentyl‐3, 4, 9, 10‐perylenedicarboximide small molecule for optoelectronic applications. Polymers For Advanced Technologies, 27(2), 144-155.
  • Imer, A. G., Kaya, E., Dere, A., Al-Sehemi, A. G., Al-Ghamdi, A. A., Karabulut, A., & Yakuphanoglu, F. (2020). Illumination impact on the electrical characteristics of Au/Sunset Yellow/n-Si/Au hybrid Schottky diode. Journal of Materials Science: Materials in Electronics, 31, 14665-14673.
  • Jhulki, S., & Moorthy, J. N. (2018). Small molecular hole-transporting materials (HTMs) in organic light-emitting diodes (OLEDs): Structural diversity and classification. Journal of Materials Chemistry C, 6(31), 8280-8325.
  • Wrona-Piotrowicz, A., Ciechańska, M., Zakrzewski, J., & Makal, A. (2016). Pyrene fluorophores bearing two carbonyl groups in 1, 2-positions: Synthesis and photophysical properties of pyrene-1, 2-dicarboximides and a pyrene-1, 2-dicarboxamide. Journal of Photochemistry and Photobiology A: Chemistry, 330, 15-21.
  • Santana-Martínez, I., Ramírez-Palma, M. T., Sánchez-Escalera, J., Martínez-Otero, D., García-Eleno, M. A., Dorazco-González, A., & Cuevas-Yañez, E. (2020). Synthesis, structural analysis, and photophysical properties of bi-1, 2, 3-triazoles. Structural Chemistry, 31, 191-201.
  • Coskun, D., Gunduz, B., & Coskun, M. F. (2019). Synthesis, characterization and significant optoelectronic parameters of 1-(7-methoxy-1-benzofuran-2-yl) substituted chalcone derivatives. Journal of molecular structure, 1178, 261-267.
  • Guillot, R., Loupy, A., Meddour, A., Pellet, M., & Petit, A. (2005). Solvent-free condensation of arylacetonitrile with aldehydes. Tetrahedron, 61(42), 10129-10137.
  • Buu-Hoi, N. P., Saint-Ruf, G., & Lobert, B. (1969). Oxygen heterocycles. Part XIV. Hydroxylated 3-aryl-and 3-pyridyl-coumarins. Journal of the Chemical Society C: Organic, (16), 2069-2070.
  • Yakalı, G., Çoban, M. B., Özen, F., Özen, L. B., Gündüz, B., & Cin, G. T. (2021). The importance of polymorphism dependent aggregation induced enhanced emission of the acrylonitrile derivative: Helical J type and antiparallel h type stacking modes. ChemistrySelect, 6(41), 11392-11406.
  • Zhang, J. Z. (2009). Optical properties and spectroscopy of nanomaterials. World Scientific.
  • Tripathy, S. K. (2015). Refractive indices of semiconductors from energy gaps. Optical materials, 46, 240-246.
  • El-Menyawy, E. M., Elagamey, A. A., Elgogary, S. R., & El-Enein, R. A. (2013). Optical, electrical and photovoltaic properties of thermally evaporated 3-amino-2-[(2-nitrophenyl) diazinyl]-3-(piperidin-1-yl) acrylonitrile thin films. Materials science in semiconductor processing, 16(6), 1828-1836.
  • Zeyada, H. M., El-Nahass, M. M., & El-Shabaan, M. M. (2016). Photovoltaic properties of the 4H-pyrano [3, 2-c] quinoline derivatives and their applications in organic–inorganic photodiode fabrication. Synthetic Metals, 220, 102-113.
  • Cheng, P., & Zhan, X. (2016). Stability of organic solar cells: challenges and strategies. Chemical Society Reviews, 45(9), 2544-2582.
  • Riede, M., Mueller, T., Tress, W., Schueppel, R., & Leo, K. (2008). Small-molecule solar cells—status and perspectives. Nanotechnology, 19(42), 424001.
  • Khapre, A., Kumar, A. V., & Chandrasekar, R. Powering Organic Flexible Optical Waveguides and Circuits via Focused Micro‐LEDs for Visible Light Communication. Laser & Photonics Reviews, 2400278.
  • Görrn, P., Lehnhardt, M., Kowalsky, W., Riedl, T., & Wagner, S. (2011). Elastically tunable self-organized organic lasers. Advanced Materials, 23(7), 869.[36] Seemann, A., Sauermann, T., Lungenschmied, C., Armbruster, O., Bauer, S., Egelhaaf, H. J., & Hauch, J. (2011). Reversible and irreversible degradation of organic solar cell performance by oxygen. Solar Energy, 85(6), 1238-1249.

Year 2024, Volume: 7 Issue: 2, 208 - 214, 18.12.2024

Leyla Babali Özen , Furkan Özen , Bayram Gündüz , Günseli Turgut Cin

https://doi.org/10.54565/jphcfum.1583947

Abstract

Project Number

TÜBİTAK, KBAG-119Z608 and AU-BAP, FBA-2020-5403 and FDK-2022-6056

References

  • Roncali, J. (2011). Single material solar cells: the next frontier for organic photovoltaics. Advanced Energy Materials, 1(2), 147-160.
  • Wang, Y., Shang, H., Li, B., & Jiang, S. (2022). Reversible luminescence “off–on” regulation based on tunable photodimerization via crystal-to-cocrystal transformation. Journal of Materials Chemistry C, 10(2), 734-741.
  • Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A., & Puschmann, H. (2009). OLEX2: a complete structure solution, refinement and analysis program. Journal of applied crystallography, 42(2), 339-341.
  • Strieth-Kalthoff, F., James, M. J., Teders, M., Pitzer, L., & Glorius, F. (2018). Energy transfer catalysis mediated by visible light: principles, applications, directions. Chemical Society Reviews, 47(19), 7190-7202.
  • Zhou, Q. Q., Zou, Y. Q., Lu, L. Q., & Xiao, W. J. (2019). Visible‐light‐induced organic photochemical reactions through energy‐transfer pathways. Angewandte Chemie International Edition, 58(6), 1586-1604.
  • Gündüz, B. (2013). Effects of molarity and solvents on the optical properties of the solutions of tris [4-(5-dicyanomethylidenemethyl-2-thienyl) phenyl] amine (TDCV-TPA) and structural properties of its film. Optical Materials, 36(2), 425-436.
  • Lloyd, M. T., Anthony, J. E., & Malliaras, G. G. (2007). Photovoltaics from soluble small molecules. Materials Today, 10(11), 34-41.
  • Anandhan, K., Cerón, M., Perumal, V., Ceballos, P., Gordillo-Guerra, P., Pérez-Gutiérrez, E., ... & Percino, M. J. (2019). Solvatochromism and pH effect on the emission of a triphenylimidazole-phenylacrylonitrile derivative: experimental and DFT studies. RSC advances, 9(21), 12085-12096.
  • Castillo, A., Ceballos, P., Santos, P., Cerón, M., Venkatesan, P., Pérez-Gutiérrez, E., ... & Percino, M. J. (2021). Solution and solid-state photophysical properties of positional Isomeric acrylonitrile derivatives with Core pyridine and phenyl moieties: experimental and DFT studies. Molecules, 26(6), 1500.
  • Jayabharathi, J., Thanikachalam, V., & Perumal, M. V. (2012). Physicochemical and solvatochromic analysis of an imidazole derivative as NLO material. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 85(1), 31-37.
  • Büchele, P., Richter, M., Tedde, S. F., Matt, G. J., Ankah, G. N., Fischer, R., ... & Schmidt, O. (2015). X-ray imaging with scintillator-sensitized hybrid organic photodetectors. Nature Photonics, 9(12), 843-848.
  • Hssain, A. H., Gündüz, B., Majid, A., & Bulut, N. (2021). NTCDA compounds of optoelectronic interest: Theoretical insights and experimental investigation. Chemical Physics Letters, 780, 138918.
  • Zhu, L., & Zhao, Y. (2013). Cyanostilbene-based intelligent organic optoelectronic materials. Journal of Materials Chemistry C, 1(6), 1059-1065.
  • Kim, M. J., An, T. K., Kim, S. O., Cha, H., Kim, H. N., Xiofeng, T., ... & Kim, Y. H. (2015). Molecular design and ordering effects of alkoxy aromatic donor in a DPP copolymer on OTFTs and OPVs. Materials Chemistry and Physics, 153, 63-71.
  • Fang, J. K., Sun, T., Tian, Y., Zhang, Y., Jin, C., Xu, Z., ... & Wang, H. (2017). Novel diyne-bridged dyes for efficient dye-sensitized solar cells. Materials Chemistry and Physics, 195, 1-9.
  • Shaikh, S. A., Mendhe, A. C., Nadimetla, D. N., Biradar, M. R., Vijayanand, P., Puyad, A. L., ... & Bhosale, S. V. (2024). Benzothiazole functionalized diketopyrrolopyrrole photosensitizer for CdS nanowire based DSSC applications. Journal of Photochemistry and Photobiology A: Chemistry, 447, 115220.
  • Sharma, G. D., Patel, K. R., Roy, M. S., & Misra, R. (2014). Characterization of two new (A–π) 2–D–A type dyes with different central D unit and their application for dye sensitized solar cells. Organic Electronics, 15(8), 1780-1790.
  • Jeong, H. G., Khim, D., Jung, E., Yun, J. M., Kim, J., Ku, J., ... & Kim, D. Y. (2013). Synthesis and characterization of a novel ambipolar polymer semiconductor based on a fumaronitrile core as an electron‐withdrawing group. Journal of Polymer Science Part A: Polymer Chemistry, 51(5), 1029-1039.
  • Gündüz, B. (2016). Investigation of the spectral, optical and surface morphology properties of the N, N′‐Dipentyl‐3, 4, 9, 10‐perylenedicarboximide small molecule for optoelectronic applications. Polymers For Advanced Technologies, 27(2), 144-155.
  • Imer, A. G., Kaya, E., Dere, A., Al-Sehemi, A. G., Al-Ghamdi, A. A., Karabulut, A., & Yakuphanoglu, F. (2020). Illumination impact on the electrical characteristics of Au/Sunset Yellow/n-Si/Au hybrid Schottky diode. Journal of Materials Science: Materials in Electronics, 31, 14665-14673.
  • Jhulki, S., & Moorthy, J. N. (2018). Small molecular hole-transporting materials (HTMs) in organic light-emitting diodes (OLEDs): Structural diversity and classification. Journal of Materials Chemistry C, 6(31), 8280-8325.
  • Wrona-Piotrowicz, A., Ciechańska, M., Zakrzewski, J., & Makal, A. (2016). Pyrene fluorophores bearing two carbonyl groups in 1, 2-positions: Synthesis and photophysical properties of pyrene-1, 2-dicarboximides and a pyrene-1, 2-dicarboxamide. Journal of Photochemistry and Photobiology A: Chemistry, 330, 15-21.
  • Santana-Martínez, I., Ramírez-Palma, M. T., Sánchez-Escalera, J., Martínez-Otero, D., García-Eleno, M. A., Dorazco-González, A., & Cuevas-Yañez, E. (2020). Synthesis, structural analysis, and photophysical properties of bi-1, 2, 3-triazoles. Structural Chemistry, 31, 191-201.
  • Coskun, D., Gunduz, B., & Coskun, M. F. (2019). Synthesis, characterization and significant optoelectronic parameters of 1-(7-methoxy-1-benzofuran-2-yl) substituted chalcone derivatives. Journal of molecular structure, 1178, 261-267.
  • Guillot, R., Loupy, A., Meddour, A., Pellet, M., & Petit, A. (2005). Solvent-free condensation of arylacetonitrile with aldehydes. Tetrahedron, 61(42), 10129-10137.
  • Buu-Hoi, N. P., Saint-Ruf, G., & Lobert, B. (1969). Oxygen heterocycles. Part XIV. Hydroxylated 3-aryl-and 3-pyridyl-coumarins. Journal of the Chemical Society C: Organic, (16), 2069-2070.
  • Yakalı, G., Çoban, M. B., Özen, F., Özen, L. B., Gündüz, B., & Cin, G. T. (2021). The importance of polymorphism dependent aggregation induced enhanced emission of the acrylonitrile derivative: Helical J type and antiparallel h type stacking modes. ChemistrySelect, 6(41), 11392-11406.
  • Zhang, J. Z. (2009). Optical properties and spectroscopy of nanomaterials. World Scientific.
  • Tripathy, S. K. (2015). Refractive indices of semiconductors from energy gaps. Optical materials, 46, 240-246.
  • El-Menyawy, E. M., Elagamey, A. A., Elgogary, S. R., & El-Enein, R. A. (2013). Optical, electrical and photovoltaic properties of thermally evaporated 3-amino-2-[(2-nitrophenyl) diazinyl]-3-(piperidin-1-yl) acrylonitrile thin films. Materials science in semiconductor processing, 16(6), 1828-1836.
  • Zeyada, H. M., El-Nahass, M. M., & El-Shabaan, M. M. (2016). Photovoltaic properties of the 4H-pyrano [3, 2-c] quinoline derivatives and their applications in organic–inorganic photodiode fabrication. Synthetic Metals, 220, 102-113.
  • Cheng, P., & Zhan, X. (2016). Stability of organic solar cells: challenges and strategies. Chemical Society Reviews, 45(9), 2544-2582.
  • Riede, M., Mueller, T., Tress, W., Schueppel, R., & Leo, K. (2008). Small-molecule solar cells—status and perspectives. Nanotechnology, 19(42), 424001.
  • Khapre, A., Kumar, A. V., & Chandrasekar, R. Powering Organic Flexible Optical Waveguides and Circuits via Focused Micro‐LEDs for Visible Light Communication. Laser & Photonics Reviews, 2400278.
  • Görrn, P., Lehnhardt, M., Kowalsky, W., Riedl, T., & Wagner, S. (2011). Elastically tunable self-organized organic lasers. Advanced Materials, 23(7), 869.[36] Seemann, A., Sauermann, T., Lungenschmied, C., Armbruster, O., Bauer, S., Egelhaaf, H. J., & Hauch, J. (2011). Reversible and irreversible degradation of organic solar cell performance by oxygen. Solar Energy, 85(6), 1238-1249.
There are 35 citations in total.

Details

Primary Language English
Subjects Material Production Technologies
Journal Section Articles
Authors

Leyla Babali Özen 0000-0001-9023-6604

Furkan Özen 0000-0003-1178-1167

Bayram Gündüz 0000-0002-1447-7534

Günseli Turgut Cin 0000-0001-9658-8344

Project Number TÜBİTAK, KBAG-119Z608 and AU-BAP, FBA-2020-5403 and FDK-2022-6056
Publication Date December 18, 2024
Submission Date November 12, 2024
Acceptance Date December 8, 2024
Published in Issue Year 2024 Volume: 7 Issue: 2

Cite

APA Babali Özen, L., Özen, F., Gündüz, B., Turgut Cin, G. (2024). Synthesis and Optical Properties of 2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds. Journal of Physical Chemistry and Functional Materials, 7(2), 208-214. https://doi.org/10.54565/jphcfum.1583947
AMA Babali Özen L, Özen F, Gündüz B, Turgut Cin G. Synthesis and Optical Properties of 2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds. Journal of Physical Chemistry and Functional Materials. December 2024;7(2):208-214. doi:10.54565/jphcfum.1583947
Chicago Babali Özen, Leyla, Furkan Özen, Bayram Gündüz, and Günseli Turgut Cin. “Synthesis and Optical Properties of 2-(4-Trifluoromethylphenyl)-3-(4-Methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds”. Journal of Physical Chemistry and Functional Materials 7, no. 2 (December 2024): 208-14. https://doi.org/10.54565/jphcfum.1583947.
EndNote Babali Özen L, Özen F, Gündüz B, Turgut Cin G (December 1, 2024) Synthesis and Optical Properties of 2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds. Journal of Physical Chemistry and Functional Materials 7 2 208–214.
IEEE L. Babali Özen, F. Özen, B. Gündüz, and G. Turgut Cin, “Synthesis and Optical Properties of 2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds”, Journal of Physical Chemistry and Functional Materials, vol. 7, no. 2, pp. 208–214, 2024, doi: 10.54565/jphcfum.1583947.
ISNAD Babali Özen, Leyla et al. “Synthesis and Optical Properties of 2-(4-Trifluoromethylphenyl)-3-(4-Methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds”. Journal of Physical Chemistry and Functional Materials 7/2 (December 2024), 208-214. https://doi.org/10.54565/jphcfum.1583947.
JAMA Babali Özen L, Özen F, Gündüz B, Turgut Cin G. Synthesis and Optical Properties of 2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds. Journal of Physical Chemistry and Functional Materials. 2024;7:208–214.
MLA Babali Özen, Leyla et al. “Synthesis and Optical Properties of 2-(4-Trifluoromethylphenyl)-3-(4-Methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds”. Journal of Physical Chemistry and Functional Materials, vol. 7, no. 2, 2024, pp. 208-14, doi:10.54565/jphcfum.1583947.
Vancouver Babali Özen L, Özen F, Gündüz B, Turgut Cin G. Synthesis and Optical Properties of 2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl) Acrylonitrile (4MPAN-TFMP) Compounds. Journal of Physical Chemistry and Functional Materials. 2024;7(2):208-14.