Fluorinated Merophosphinine and Phosphinine Dyes: Synthesis and Evaluation of UV-Visible Light Absorption Properties
Merophosphinine and phosphinine dyes were reported as phosphorus atom equivalents of merocyanine and cyanine dyes in the 1960s. Although these dyes are excellent sensitizers for enhancing photographic performance, their development has been considerably retarded because of difficulties in the synthe...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Compounds |
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| Online Access: | https://www.mdpi.com/2673-6918/3/1/13 |
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| author | Shigeyuki Yamada Yusuke Takahashi Tsutomu Konno |
| author_facet | Shigeyuki Yamada Yusuke Takahashi Tsutomu Konno |
| author_sort | Shigeyuki Yamada |
| collection | DOAJ |
| description | Merophosphinine and phosphinine dyes were reported as phosphorus atom equivalents of merocyanine and cyanine dyes in the 1960s. Although these dyes are excellent sensitizers for enhancing photographic performance, their development has been considerably retarded because of difficulties in the synthetic process. Previously, while investigating the reactivity of fluoroalkenes with various nucleophiles, we developed fluorinated merophosphinine and phosphinine scaffolds in a single reaction step; however, we did not investigate their ultraviolet-visible (UV-vis) light absorption properties further. Therefore, in this study, we synthesized fluorinated merophosphinines and phosphinine derivatives using triphenylphosphonium ylides with various R substituents [R = H, C<sub>6</sub>H<sub>5</sub>, 4-MeOC<sub>6</sub>H<sub>4</sub>, 4-PhC<sub>6</sub>H<sub>4</sub>, or C<sub>6</sub>F<sub>5</sub>] and octafluorocyclopentene to study their absorption characteristics. Thermogravimetric analyses (TGA) indicated that several synthesized derivatives were thermally stable at temperatures above 241 °C. Additionally, when studied in various solvents, the fluorinated merophosphinine and phosphinine dyes exhibited well-defined maximum absorption wavelengths (<i>λ</i><sub>abs</sub>) in the 364–375 and 420–474 nm ranges, respectively. Thus, fluorinated merophosphinine and phosphinine derivatives may serve as promising thermally stable functional dyes for future technical applications. |
| first_indexed | 2024-03-11T06:44:01Z |
| format | Article |
| id | doaj.art-b8a8471c52c04a468bc7b1bea5381143 |
| institution | Directory Open Access Journal |
| issn | 2673-6918 |
| language | English |
| last_indexed | 2024-03-11T06:44:01Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Compounds |
| spelling | doaj.art-b8a8471c52c04a468bc7b1bea53811432023-11-17T10:25:49ZengMDPI AGCompounds2673-69182023-02-013115316810.3390/compounds3010013Fluorinated Merophosphinine and Phosphinine Dyes: Synthesis and Evaluation of UV-Visible Light Absorption PropertiesShigeyuki Yamada0Yusuke Takahashi1Tsutomu Konno2Faculty of Molecular Chemistry and Materials Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, JapanFaculty of Molecular Chemistry and Materials Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, JapanFaculty of Molecular Chemistry and Materials Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, JapanMerophosphinine and phosphinine dyes were reported as phosphorus atom equivalents of merocyanine and cyanine dyes in the 1960s. Although these dyes are excellent sensitizers for enhancing photographic performance, their development has been considerably retarded because of difficulties in the synthetic process. Previously, while investigating the reactivity of fluoroalkenes with various nucleophiles, we developed fluorinated merophosphinine and phosphinine scaffolds in a single reaction step; however, we did not investigate their ultraviolet-visible (UV-vis) light absorption properties further. Therefore, in this study, we synthesized fluorinated merophosphinines and phosphinine derivatives using triphenylphosphonium ylides with various R substituents [R = H, C<sub>6</sub>H<sub>5</sub>, 4-MeOC<sub>6</sub>H<sub>4</sub>, 4-PhC<sub>6</sub>H<sub>4</sub>, or C<sub>6</sub>F<sub>5</sub>] and octafluorocyclopentene to study their absorption characteristics. Thermogravimetric analyses (TGA) indicated that several synthesized derivatives were thermally stable at temperatures above 241 °C. Additionally, when studied in various solvents, the fluorinated merophosphinine and phosphinine dyes exhibited well-defined maximum absorption wavelengths (<i>λ</i><sub>abs</sub>) in the 364–375 and 420–474 nm ranges, respectively. Thus, fluorinated merophosphinine and phosphinine derivatives may serve as promising thermally stable functional dyes for future technical applications.https://www.mdpi.com/2673-6918/3/1/13fluorinemerophosphininesphosphininesfunctional dyes |
| spellingShingle | Shigeyuki Yamada Yusuke Takahashi Tsutomu Konno Fluorinated Merophosphinine and Phosphinine Dyes: Synthesis and Evaluation of UV-Visible Light Absorption Properties Compounds fluorine merophosphinines phosphinines functional dyes |
| title | Fluorinated Merophosphinine and Phosphinine Dyes: Synthesis and Evaluation of UV-Visible Light Absorption Properties |
| title_full | Fluorinated Merophosphinine and Phosphinine Dyes: Synthesis and Evaluation of UV-Visible Light Absorption Properties |
| title_fullStr | Fluorinated Merophosphinine and Phosphinine Dyes: Synthesis and Evaluation of UV-Visible Light Absorption Properties |
| title_full_unstemmed | Fluorinated Merophosphinine and Phosphinine Dyes: Synthesis and Evaluation of UV-Visible Light Absorption Properties |
| title_short | Fluorinated Merophosphinine and Phosphinine Dyes: Synthesis and Evaluation of UV-Visible Light Absorption Properties |
| title_sort | fluorinated merophosphinine and phosphinine dyes synthesis and evaluation of uv visible light absorption properties |
| topic | fluorine merophosphinines phosphinines functional dyes |
| url | https://www.mdpi.com/2673-6918/3/1/13 |
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