Scalable Synthesis of Multivalent Macromonomers for ROMP
The polymerization of functional monomers provides direct access to functional polymers without need for postpolymerization modification; however, monomer synthesis can become a bottleneck of this approach. New methods that enable rapid installation of functionality into monomers for living polymeri...
| Main Authors: | , , , , , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
American Chemical Society (ACS)
2020
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| Online Access: | https://hdl.handle.net/1721.1/125611 |
| _version_ | 1826205155156033536 |
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| author | Nguyen, Hung VanThanh Gallagher, Nolan Vohidov, Farrukh Jiang, Yivan Kawamoto, Ken Park, Jiwon Huang, Zhihao Johnson, Jeremiah A. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Nguyen, Hung VanThanh Gallagher, Nolan Vohidov, Farrukh Jiang, Yivan Kawamoto, Ken Park, Jiwon Huang, Zhihao Johnson, Jeremiah A. |
| author_sort | Nguyen, Hung VanThanh |
| collection | MIT |
| description | The polymerization of functional monomers provides direct access to functional polymers without need for postpolymerization modification; however, monomer synthesis can become a bottleneck of this approach. New methods that enable rapid installation of functionality into monomers for living polymerization are valuable. Here, we report the three-step convergent synthesis (two-step longest linear sequence) of a divalent exo-norbornene imide capable of efficient coupling with various nucleophiles and azides to produce diversely functionalized branched macromonomers optimized for ring-opening metathesis polymerization (ROMP). In addition, we describe an efficient iterative procedure for the synthesis of tri- and tetra-valent branched macromonomers. We demonstrate the use of these branched macromonomers for the synthesis of Janus bottlebrush block copolymers as well as for the generation of bottlebrush polymers with up to three conjugated small molecules per repeat unit. This work significantly expands the scalability and diversity of nanostructured macromolecules accessible via ROMP. |
| first_indexed | 2024-09-23T13:08:16Z |
| format | Article |
| id | mit-1721.1/125611 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T13:08:16Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1256112022-10-01T13:15:46Z Scalable Synthesis of Multivalent Macromonomers for ROMP Nguyen, Hung VanThanh Gallagher, Nolan Vohidov, Farrukh Jiang, Yivan Kawamoto, Ken Park, Jiwon Huang, Zhihao Johnson, Jeremiah A. Massachusetts Institute of Technology. Department of Chemistry The polymerization of functional monomers provides direct access to functional polymers without need for postpolymerization modification; however, monomer synthesis can become a bottleneck of this approach. New methods that enable rapid installation of functionality into monomers for living polymerization are valuable. Here, we report the three-step convergent synthesis (two-step longest linear sequence) of a divalent exo-norbornene imide capable of efficient coupling with various nucleophiles and azides to produce diversely functionalized branched macromonomers optimized for ring-opening metathesis polymerization (ROMP). In addition, we describe an efficient iterative procedure for the synthesis of tri- and tetra-valent branched macromonomers. We demonstrate the use of these branched macromonomers for the synthesis of Janus bottlebrush block copolymers as well as for the generation of bottlebrush polymers with up to three conjugated small molecules per repeat unit. This work significantly expands the scalability and diversity of nanostructured macromolecules accessible via ROMP. National Institutes of Health (U.S.) (Grant 1R01CA220468-01) United States. Air Force. Office of Scientific Research (Grant FA9550-14-1-0292) United States. Department of Energy. Office of Science (Contract DE-AC02-06CH11357) United States. Department of Energy. Office of Science (Contract DE-SC0012704) 2020-06-02T16:48:34Z 2020-06-02T16:48:34Z 2018-04 2019-12-20T16:42:50Z Article http://purl.org/eprint/type/JournalArticle 2161-1653 https://hdl.handle.net/1721.1/125611 Nguyen, Hung V.-T. et al. “Scalable Synthesis of Multivalent Macromonomers for ROMP.” ACS macro letters 7 (2018): 472-476 © 2018 The Author(s) en https://dx.doi.org/10.1021/ACSMACROLETT.8B00201 ACS macro letters Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Nguyen, Hung VanThanh Gallagher, Nolan Vohidov, Farrukh Jiang, Yivan Kawamoto, Ken Park, Jiwon Huang, Zhihao Johnson, Jeremiah A. Scalable Synthesis of Multivalent Macromonomers for ROMP |
| title | Scalable Synthesis of Multivalent Macromonomers for ROMP |
| title_full | Scalable Synthesis of Multivalent Macromonomers for ROMP |
| title_fullStr | Scalable Synthesis of Multivalent Macromonomers for ROMP |
| title_full_unstemmed | Scalable Synthesis of Multivalent Macromonomers for ROMP |
| title_short | Scalable Synthesis of Multivalent Macromonomers for ROMP |
| title_sort | scalable synthesis of multivalent macromonomers for romp |
| url | https://hdl.handle.net/1721.1/125611 |
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