Cyclobutene based macrocycles
© the Partner Organisations. Nanoscopic macrocycles could have unusual magnetic, optical, and electronic properties when compared to their linear counterparts. Conjugated π-systems in unsaturated macrocycles are particularly interesting as they have no end groups that limit electronic delocalization...
| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
Royal Society of Chemistry (RSC)
2021
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| Online Access: | https://hdl.handle.net/1721.1/137266 |
| _version_ | 1826198656721616896 |
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| author | Wang, Pan Lu, Ruqiang France-Lanord, Arthur Wang, Yanming Zhou, Jingjing Grossman, Jeffrey C Swager, Timothy M |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Wang, Pan Lu, Ruqiang France-Lanord, Arthur Wang, Yanming Zhou, Jingjing Grossman, Jeffrey C Swager, Timothy M |
| author_sort | Wang, Pan |
| collection | MIT |
| description | © the Partner Organisations. Nanoscopic macrocycles could have unusual magnetic, optical, and electronic properties when compared to their linear counterparts. Conjugated π-systems in unsaturated macrocycles are particularly interesting as they have no end groups that limit electronic delocalization in equivalent linear oligomers. The rigid four-membered ring structure in 3,4-bis(methylene)cyclobutene with vicinal connections provides a vertex with an angle slightly less than 90°, which promotes macrocycle formation. We report herein a facile high-yielding synthesis of a series of 3,4-bis(methylene)cyclobutene-base π-conjugation macrocycles. The structure-property studies reveal that the smaller macrocycles are rigid crystalline frameworks and display symmetrical conformations in solution. The electrochemical, photophysical and magnetic properties of these macrocycles were also studied with a framework of characterization methods, revealing their size- and linkage-dependent properties. Density functional theory (DFT) calculations and molecular dynamics (MD) simulations at the molecular level suggest that several possible configurations are possible for macrocycles with larger ring sizes. |
| first_indexed | 2024-09-23T11:08:10Z |
| format | Article |
| id | mit-1721.1/137266 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T11:08:10Z |
| publishDate | 2021 |
| publisher | Royal Society of Chemistry (RSC) |
| record_format | dspace |
| spelling | mit-1721.1/1372662023-02-09T15:55:40Z Cyclobutene based macrocycles Wang, Pan Lu, Ruqiang France-Lanord, Arthur Wang, Yanming Zhou, Jingjing Grossman, Jeffrey C Swager, Timothy M Massachusetts Institute of Technology. Department of Chemistry Massachusetts Institute of Technology. Department of Materials Science and Engineering © the Partner Organisations. Nanoscopic macrocycles could have unusual magnetic, optical, and electronic properties when compared to their linear counterparts. Conjugated π-systems in unsaturated macrocycles are particularly interesting as they have no end groups that limit electronic delocalization in equivalent linear oligomers. The rigid four-membered ring structure in 3,4-bis(methylene)cyclobutene with vicinal connections provides a vertex with an angle slightly less than 90°, which promotes macrocycle formation. We report herein a facile high-yielding synthesis of a series of 3,4-bis(methylene)cyclobutene-base π-conjugation macrocycles. The structure-property studies reveal that the smaller macrocycles are rigid crystalline frameworks and display symmetrical conformations in solution. The electrochemical, photophysical and magnetic properties of these macrocycles were also studied with a framework of characterization methods, revealing their size- and linkage-dependent properties. Density functional theory (DFT) calculations and molecular dynamics (MD) simulations at the molecular level suggest that several possible configurations are possible for macrocycles with larger ring sizes. 2021-11-03T17:48:59Z 2021-11-03T17:48:59Z 2020 2021-11-03T17:46:16Z Article http://purl.org/eprint/type/JournalArticle https://hdl.handle.net/1721.1/137266 Wang, Pan, Lu, Ruqiang, France-Lanord, Arthur, Wang, Yanming, Zhou, Jingjing et al. 2020. "Cyclobutene based macrocycles." Materials Chemistry Frontiers, 4 (12). en 10.1039/D0QM00824A Materials Chemistry Frontiers Creative Commons Attribution NonCommercial License 4.0 https://creativecommons.org/licenses/by-nc/4.0/ application/pdf Royal Society of Chemistry (RSC) Royal Society of Chemistry (RSC) |
| spellingShingle | Wang, Pan Lu, Ruqiang France-Lanord, Arthur Wang, Yanming Zhou, Jingjing Grossman, Jeffrey C Swager, Timothy M Cyclobutene based macrocycles |
| title | Cyclobutene based macrocycles |
| title_full | Cyclobutene based macrocycles |
| title_fullStr | Cyclobutene based macrocycles |
| title_full_unstemmed | Cyclobutene based macrocycles |
| title_short | Cyclobutene based macrocycles |
| title_sort | cyclobutene based macrocycles |
| url | https://hdl.handle.net/1721.1/137266 |
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