Fluorous phthalocyanines and subphthalocyanines
© 2020 World Scientific Publishing Company. Incorporating fluorine atoms into a molecule can endow it with various unique properties that enable materials applications. Selective solubility in fluorous solvents is achieved by a high fluorine content and selective partitioning into perfluorinated liq...
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| Format: | Article |
| Language: | English |
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World Scientific Pub Co Pte Lt
2020
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| Online Access: | https://hdl.handle.net/1721.1/128241 |
| _version_ | 1826205904120315904 |
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| author | Yoshinaga, Kosuke Delage-Laurin, Leo Swager, Timothy M |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Yoshinaga, Kosuke Delage-Laurin, Leo Swager, Timothy M |
| author_sort | Yoshinaga, Kosuke |
| collection | MIT |
| description | © 2020 World Scientific Publishing Company. Incorporating fluorine atoms into a molecule can endow it with various unique properties that enable materials applications. Selective solubility in fluorous solvents is achieved by a high fluorine content and selective partitioning into perfluorinated liquids over organic and aqueous phases provides orthogonal opportunities for chemistry and materials assembly. Although there is a growing number of partially fluorinated molecules, there are insufficient structural design principles to produce diverse fluorous soluble dyes. Herein, we report the synthesis of six fluorous phthalocyanine and subphthalocyanine dyes, and study their properties in the fluorous phase. Phthalocyanines generally display limited solubility and we also observed apparent aggregation in the fluorous phase. However, the nonplanar subphthalocyanines showed greater solubility. Subphthalocyanines also displayed fluorescence in selected solvents, and their emissive properties were investigated. The materials described expand the library of fluorous dyes and provide insights for the design of new molecules with fluorous solubility. |
| first_indexed | 2024-09-23T13:20:53Z |
| format | Article |
| id | mit-1721.1/128241 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T13:20:53Z |
| publishDate | 2020 |
| publisher | World Scientific Pub Co Pte Lt |
| record_format | dspace |
| spelling | mit-1721.1/1282412020-10-30T03:16:01Z Fluorous phthalocyanines and subphthalocyanines Yoshinaga, Kosuke Delage-Laurin, Leo Swager, Timothy M Massachusetts Institute of Technology. Department of Chemistry © 2020 World Scientific Publishing Company. Incorporating fluorine atoms into a molecule can endow it with various unique properties that enable materials applications. Selective solubility in fluorous solvents is achieved by a high fluorine content and selective partitioning into perfluorinated liquids over organic and aqueous phases provides orthogonal opportunities for chemistry and materials assembly. Although there is a growing number of partially fluorinated molecules, there are insufficient structural design principles to produce diverse fluorous soluble dyes. Herein, we report the synthesis of six fluorous phthalocyanine and subphthalocyanine dyes, and study their properties in the fluorous phase. Phthalocyanines generally display limited solubility and we also observed apparent aggregation in the fluorous phase. However, the nonplanar subphthalocyanines showed greater solubility. Subphthalocyanines also displayed fluorescence in selected solvents, and their emissive properties were investigated. The materials described expand the library of fluorous dyes and provide insights for the design of new molecules with fluorous solubility. 2020-10-29T14:51:27Z 2020-10-29T14:51:27Z 2020-10-05T14:11:12Z Article http://purl.org/eprint/type/JournalArticle 1088-4246 https://hdl.handle.net/1721.1/128241 Yoshinaga, Kosuke, Delage-Laurin, Leo and Swager, Timothy M. "Fluorous phthalocyanines and subphthalocyanines." Journal of Porphyrins and Phthalocyanines, 24 (8). en 10.1142/S1088424620500182 Journal of Porphyrins and Phthalocyanines Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf World Scientific Pub Co Pte Lt Prof. Swager via Ye Li |
| spellingShingle | Yoshinaga, Kosuke Delage-Laurin, Leo Swager, Timothy M Fluorous phthalocyanines and subphthalocyanines |
| title | Fluorous phthalocyanines and subphthalocyanines |
| title_full | Fluorous phthalocyanines and subphthalocyanines |
| title_fullStr | Fluorous phthalocyanines and subphthalocyanines |
| title_full_unstemmed | Fluorous phthalocyanines and subphthalocyanines |
| title_short | Fluorous phthalocyanines and subphthalocyanines |
| title_sort | fluorous phthalocyanines and subphthalocyanines |
| url | https://hdl.handle.net/1721.1/128241 |
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