Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine
Two macrocyclic Schiff bases derived from o-phenylenediamine and 2-hydroxy-5-methylisophthalaldehyde <b>L1</b> or 2-hydroxy-5-tert-butyl-1,3-benzenedicarboxaldehyde <b>L2</b>, respectively, were obtained and characterized by X-ray crystallography and spectroscopy (UV-vis, flu...
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/21/7396 |
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| author | Magdalena Barwiolek Dominika Jankowska Anna Kaczmarek-Kędziera Slawomir Wojtulewski Lukasz Skowroński Tomasz Rerek Paweł Popielarski Tadeusz M. Muziol |
| author_facet | Magdalena Barwiolek Dominika Jankowska Anna Kaczmarek-Kędziera Slawomir Wojtulewski Lukasz Skowroński Tomasz Rerek Paweł Popielarski Tadeusz M. Muziol |
| author_sort | Magdalena Barwiolek |
| collection | DOAJ |
| description | Two macrocyclic Schiff bases derived from o-phenylenediamine and 2-hydroxy-5-methylisophthalaldehyde <b>L1</b> or 2-hydroxy-5-tert-butyl-1,3-benzenedicarboxaldehyde <b>L2</b>, respectively, were obtained and characterized by X-ray crystallography and spectroscopy (UV-vis, fluorescence and IR). X-ray crystal structure determination and DFT calculations for compounds confirmed their geometry in solution and in the solid phase. Moreover, intermolecular interactions in the crystal structure of <b>L1</b> and <b>L2</b> were analyzed using 3D Hirshfeld surfaces and the related 2D fingerprint plots. The 3D Hirschfeld analyses show that the most numerous interactions were found between hydrogen atoms. A considerable number of such interactions are justified by the presence of bulk <i>tert</i>-butyl groups in <b>L2</b>. The luminescence of <b>L1</b> and <b>L2</b> in various solvents and in the solid state was studied. In general, the quantum efficiency between 0.14 and 0.70 was noted. The increase in the quantum efficiency with the solvent polarity in the case of <b>L1</b> was observed (λ<sub>ex</sub> = 350 nm). For <b>L2</b>, this trend is similar, except for the chloroform. In the solid state, emission was registered at 552 nm and 561 nm (λ<sub>ex</sub> = 350 nm) for <b>L1</b> and <b>L2</b>, respectively. Thin layers of the studied compounds were deposited on Si(111) by the spin coating method or by thermal vapor deposition and studied by scanning electron microscopy (SEM/EDS), atomic force microscopy (AFM), spectroscopic ellipsometry and fluorescence spectroscopy. The ellipsometric analysis of thin materials obtained by thermal vapor deposition showed that the band-gap energy was 3.45 ± 0.02 eV (359 ± 2 nm) and 3.29 ± 0.02 eV (377 ± 2 nm) for <b>L1</b>/Si and <b>L2</b>/Si samples, respectively. Furthermore, the materials of the <b>L1</b>/Si and <b>L2</b>/Si exhibited broad emission. This feature can allow for using these compounds in LED diodes. |
| first_indexed | 2024-03-09T18:47:52Z |
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| id | doaj.art-4e979149c5d94feb81701f3fac84631a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:47:52Z |
| publishDate | 2022-10-01 |
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| spelling | doaj.art-4e979149c5d94feb81701f3fac84631a2023-11-24T06:03:33ZengMDPI AGMolecules1420-30492022-10-012721739610.3390/molecules27217396Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-PhenylenediamineMagdalena Barwiolek0Dominika Jankowska1Anna Kaczmarek-Kędziera2Slawomir Wojtulewski3Lukasz Skowroński4Tomasz Rerek5Paweł Popielarski6Tadeusz M. Muziol7Faculty of Chemistry, Nicolaus Copernicus University in Torun, Gagarina 7, 87-100 Torun, PolandFaculty of Chemistry, Nicolaus Copernicus University in Torun, Gagarina 7, 87-100 Torun, PolandFaculty of Chemistry, Nicolaus Copernicus University in Torun, Gagarina 7, 87-100 Torun, PolandFaculty of Chemistry, University of Białystok, Ciolkowskiego 1K, 15-245 Białystok, PolandFaculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Kaliskiego 7, 85-796 Bydgoszcz, PolandFaculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Kaliskiego 7, 85-796 Bydgoszcz, PolandInstitute of Physics, Kazimierz Wielki University, Chodkiewicza 30, 85-064 Bydgoszcz, PolandFaculty of Chemistry, Nicolaus Copernicus University in Torun, Gagarina 7, 87-100 Torun, PolandTwo macrocyclic Schiff bases derived from o-phenylenediamine and 2-hydroxy-5-methylisophthalaldehyde <b>L1</b> or 2-hydroxy-5-tert-butyl-1,3-benzenedicarboxaldehyde <b>L2</b>, respectively, were obtained and characterized by X-ray crystallography and spectroscopy (UV-vis, fluorescence and IR). X-ray crystal structure determination and DFT calculations for compounds confirmed their geometry in solution and in the solid phase. Moreover, intermolecular interactions in the crystal structure of <b>L1</b> and <b>L2</b> were analyzed using 3D Hirshfeld surfaces and the related 2D fingerprint plots. The 3D Hirschfeld analyses show that the most numerous interactions were found between hydrogen atoms. A considerable number of such interactions are justified by the presence of bulk <i>tert</i>-butyl groups in <b>L2</b>. The luminescence of <b>L1</b> and <b>L2</b> in various solvents and in the solid state was studied. In general, the quantum efficiency between 0.14 and 0.70 was noted. The increase in the quantum efficiency with the solvent polarity in the case of <b>L1</b> was observed (λ<sub>ex</sub> = 350 nm). For <b>L2</b>, this trend is similar, except for the chloroform. In the solid state, emission was registered at 552 nm and 561 nm (λ<sub>ex</sub> = 350 nm) for <b>L1</b> and <b>L2</b>, respectively. Thin layers of the studied compounds were deposited on Si(111) by the spin coating method or by thermal vapor deposition and studied by scanning electron microscopy (SEM/EDS), atomic force microscopy (AFM), spectroscopic ellipsometry and fluorescence spectroscopy. The ellipsometric analysis of thin materials obtained by thermal vapor deposition showed that the band-gap energy was 3.45 ± 0.02 eV (359 ± 2 nm) and 3.29 ± 0.02 eV (377 ± 2 nm) for <b>L1</b>/Si and <b>L2</b>/Si samples, respectively. Furthermore, the materials of the <b>L1</b>/Si and <b>L2</b>/Si exhibited broad emission. This feature can allow for using these compounds in LED diodes.https://www.mdpi.com/1420-3049/27/21/7396Schiff basesellipsometryDFTfluorescenceX-raythin layer |
| spellingShingle | Magdalena Barwiolek Dominika Jankowska Anna Kaczmarek-Kędziera Slawomir Wojtulewski Lukasz Skowroński Tomasz Rerek Paweł Popielarski Tadeusz M. Muziol Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine Molecules Schiff bases ellipsometry DFT fluorescence X-ray thin layer |
| title | Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine |
| title_full | Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine |
| title_fullStr | Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine |
| title_full_unstemmed | Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine |
| title_short | Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine |
| title_sort | experimental and theoretical studies of the optical properties of the schiff bases and their materials obtained from o phenylenediamine |
| topic | Schiff bases ellipsometry DFT fluorescence X-ray thin layer |
| url | https://www.mdpi.com/1420-3049/27/21/7396 |
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