Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes
Novel fluorescent dyes such as difluoroborane complexes of 1-phenylazonaphthalen-2-ol derivatives were successfully synthesized and characterized with a focus on the influence of a substituent and a solvent on the basic photophysical properties. <sup>1</sup>H, <sup>11</sup>B,...
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MDPI AG
2021-06-01
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| Online Access: | https://www.mdpi.com/1996-1944/14/12/3387 |
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| author | Agnieszka Skotnicka Przemysław Czeleń |
| author_facet | Agnieszka Skotnicka Przemysław Czeleń |
| author_sort | Agnieszka Skotnicka |
| collection | DOAJ |
| description | Novel fluorescent dyes such as difluoroborane complexes of 1-phenylazonaphthalen-2-ol derivatives were successfully synthesized and characterized with a focus on the influence of a substituent and a solvent on the basic photophysical properties. <sup>1</sup>H, <sup>11</sup>B, <sup>13</sup>C, <sup>15</sup>N, and <sup>19</sup>F nuclear magnetic resonance (NMR) spectra of substituted 1-phenylazonaphthalen-2-ol difluoroboranes and their parent azo dyes were recorded and discussed. The absorption and emission properties of synthesized compounds were investigated in solvents of varying polarity. They were found to be fluorescent despite the presence of the azo group. The azo group rotation was blocked by complexing with -BF<sub>2</sub> to get a red shift in absorption. Solvent-dependent spectral properties of compounds were investigated using Lipper-Mataga and Bakhshiev plot. The calculated DFT energies and Frontier Molecular Orbitals calculations of the studied compounds were proved to be consistent with the experimental observations. |
| first_indexed | 2024-03-10T10:16:24Z |
| format | Article |
| id | doaj.art-41612dcf1d154783abf8451a46ee5679 |
| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-10T10:16:24Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Materials |
| spelling | doaj.art-41612dcf1d154783abf8451a46ee56792023-11-22T00:44:27ZengMDPI AGMaterials1996-19442021-06-011412338710.3390/ma14123387Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes ComplexesAgnieszka Skotnicka0Przemysław Czeleń1Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, PolandDepartment of Physical Chemistry, Faculty of Pharmacy, Collegium Medicum, N. Copernicus University, Kurpińskiego 5, 85-950 Bydgoszcz, PolandNovel fluorescent dyes such as difluoroborane complexes of 1-phenylazonaphthalen-2-ol derivatives were successfully synthesized and characterized with a focus on the influence of a substituent and a solvent on the basic photophysical properties. <sup>1</sup>H, <sup>11</sup>B, <sup>13</sup>C, <sup>15</sup>N, and <sup>19</sup>F nuclear magnetic resonance (NMR) spectra of substituted 1-phenylazonaphthalen-2-ol difluoroboranes and their parent azo dyes were recorded and discussed. The absorption and emission properties of synthesized compounds were investigated in solvents of varying polarity. They were found to be fluorescent despite the presence of the azo group. The azo group rotation was blocked by complexing with -BF<sub>2</sub> to get a red shift in absorption. Solvent-dependent spectral properties of compounds were investigated using Lipper-Mataga and Bakhshiev plot. The calculated DFT energies and Frontier Molecular Orbitals calculations of the studied compounds were proved to be consistent with the experimental observations.https://www.mdpi.com/1996-1944/14/12/3387difluoroboranessubstituent effectsynthesisspectroscopic properties |
| spellingShingle | Agnieszka Skotnicka Przemysław Czeleń Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes Materials difluoroboranes substituent effect synthesis spectroscopic properties |
| title | Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes |
| title_full | Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes |
| title_fullStr | Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes |
| title_full_unstemmed | Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes |
| title_short | Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes |
| title_sort | substituent and solvent polarity on the spectroscopic properties in azo derivatives of 2 hydroxynaphthalene and their difluoroboranes complexes |
| topic | difluoroboranes substituent effect synthesis spectroscopic properties |
| url | https://www.mdpi.com/1996-1944/14/12/3387 |
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