A Showcase of Functional Fluorous Materials and Their Applications
This thesis highlights conjugated organic materials functionalized with fluoroalkyl chains and explores their applications in material chemistry. In Chapter 1, we begin with a brief introduction of incorporation of fluorine into materials and its effect on materials properties. An introduction to dy...
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| Format: | Thesis |
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Massachusetts Institute of Technology
2022
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| Online Access: | https://hdl.handle.net/1721.1/144091 https://orcid.org/0000-0002-3365-1155 |
| _version_ | 1826214145221984256 |
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| author | Yoshinaga, Kosuke |
| author2 | Swager, Timothy M. |
| author_facet | Swager, Timothy M. Yoshinaga, Kosuke |
| author_sort | Yoshinaga, Kosuke |
| collection | MIT |
| description | This thesis highlights conjugated organic materials functionalized with fluoroalkyl chains and explores their applications in material chemistry. In Chapter 1, we begin with a brief introduction of incorporation of fluorine into materials and its effect on materials properties. An introduction to dynamically reconfigurable complex emulsions reported by our group and their applications in sensing is also provided. In Chapter 2, we disclose the synthesis and photophysical properties of “fluorofluorescent” perylene bisimides, where fluoro- refers to both fluorine and fluorescence. These perylene bisimides were utilized to realize the concept of a fluorofluorescent solar concentrator. In Chapter 3, we report the synthesis and photophysical properties of fluorous phthalocyanines and subphthalocyanines. We then explored these molecules’ Faraday rotation properties in organic and fluorous solvents. In Chapter 4, we describe the applications of the perylene bisimide and subphthalocyanine dyes by incorporating them into fluorescent Janus emulsions. We also report the synthesis of fluorous soluble black hole quencher dyes, which were found to be more absorptive than fluorous soluble subphthalocyanines. The emulsions were engineered to function as biosensors for the detection of Salmonella, Zika virus, Listeria, and antiSARS-CoV-2 spike antibody. In Chapter 5, we report the utilization of the Heck reaction for facile access to functional fluorous materials. We also showcase how this fluoroalkenyl side chain turns out to be an important functional group for lithium primary batteries. |
| first_indexed | 2024-09-23T16:00:31Z |
| format | Thesis |
| id | mit-1721.1/144091 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T16:00:31Z |
| publishDate | 2022 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/1440912022-07-28T03:03:25Z A Showcase of Functional Fluorous Materials and Their Applications Yoshinaga, Kosuke Swager, Timothy M. Massachusetts Institute of Technology. Department of Chemistry This thesis highlights conjugated organic materials functionalized with fluoroalkyl chains and explores their applications in material chemistry. In Chapter 1, we begin with a brief introduction of incorporation of fluorine into materials and its effect on materials properties. An introduction to dynamically reconfigurable complex emulsions reported by our group and their applications in sensing is also provided. In Chapter 2, we disclose the synthesis and photophysical properties of “fluorofluorescent” perylene bisimides, where fluoro- refers to both fluorine and fluorescence. These perylene bisimides were utilized to realize the concept of a fluorofluorescent solar concentrator. In Chapter 3, we report the synthesis and photophysical properties of fluorous phthalocyanines and subphthalocyanines. We then explored these molecules’ Faraday rotation properties in organic and fluorous solvents. In Chapter 4, we describe the applications of the perylene bisimide and subphthalocyanine dyes by incorporating them into fluorescent Janus emulsions. We also report the synthesis of fluorous soluble black hole quencher dyes, which were found to be more absorptive than fluorous soluble subphthalocyanines. The emulsions were engineered to function as biosensors for the detection of Salmonella, Zika virus, Listeria, and antiSARS-CoV-2 spike antibody. In Chapter 5, we report the utilization of the Heck reaction for facile access to functional fluorous materials. We also showcase how this fluoroalkenyl side chain turns out to be an important functional group for lithium primary batteries. Ph.D. 2022-07-27T18:21:40Z 2022-07-27T18:21:40Z 2021-09 2022-07-27T11:43:40.839Z Thesis https://hdl.handle.net/1721.1/144091 https://orcid.org/0000-0002-3365-1155 In Copyright - Educational Use Permitted Copyright MIT http://rightsstatements.org/page/InC-EDU/1.0/ application/pdf Massachusetts Institute of Technology |
| spellingShingle | Yoshinaga, Kosuke A Showcase of Functional Fluorous Materials and Their Applications |
| title | A Showcase of Functional Fluorous Materials and Their Applications |
| title_full | A Showcase of Functional Fluorous Materials and Their Applications |
| title_fullStr | A Showcase of Functional Fluorous Materials and Their Applications |
| title_full_unstemmed | A Showcase of Functional Fluorous Materials and Their Applications |
| title_short | A Showcase of Functional Fluorous Materials and Their Applications |
| title_sort | showcase of functional fluorous materials and their applications |
| url | https://hdl.handle.net/1721.1/144091 https://orcid.org/0000-0002-3365-1155 |
| work_keys_str_mv | AT yoshinagakosuke ashowcaseoffunctionalfluorousmaterialsandtheirapplications AT yoshinagakosuke showcaseoffunctionalfluorousmaterialsandtheirapplications |