Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes
The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels–Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through comple...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2018
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| Online Access: | http://hdl.handle.net/1721.1/116849 https://orcid.org/0000-0002-1608-1330 https://orcid.org/0000-0002-6027-042X |
| _version_ | 1811096638116069376 |
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| author | Dengiz, Cagatay Luppino, Sarah Gutierrez, Gregory D. Swager, Timothy M |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Dengiz, Cagatay Luppino, Sarah Gutierrez, Gregory D. Swager, Timothy M |
| author_sort | Dengiz, Cagatay |
| collection | MIT |
| description | The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels–Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF₂, as observed by ¹H NMR analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels–Alder adduct 10 is additionally demonstrated and enables us to direct its subsequent reactivity. Finally, this work serves to demonstrate the potential for naphthazarin as a building block in the synthesis of novel organic electronic materials. |
| first_indexed | 2024-09-23T16:46:48Z |
| format | Article |
| id | mit-1721.1/116849 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:46:48Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1168492022-10-03T08:16:31Z Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes Dengiz, Cagatay Luppino, Sarah Gutierrez, Gregory D. Swager, Timothy M Massachusetts Institute of Technology. Department of Chemistry Swager, Timothy M Dengiz, Cagatay Luppino, Sarah Gutierrez, Gregory D. Swager, Timothy M The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels–Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF₂, as observed by ¹H NMR analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels–Alder adduct 10 is additionally demonstrated and enables us to direct its subsequent reactivity. Finally, this work serves to demonstrate the potential for naphthazarin as a building block in the synthesis of novel organic electronic materials. National Science Foundation (U.S.) (Grant DMR-1410718) 2018-07-09T13:58:20Z 2018-07-09T13:58:20Z 2017-07 2017-05 Article http://purl.org/eprint/type/JournalArticle 0022-3263 1520-6904 http://hdl.handle.net/1721.1/116849 Dengiz, Cagatay, et al. “Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes.” The Journal of Organic Chemistry 82, 14 (July 2017): 7470–7480 © 2017 American Chemical Society https://orcid.org/0000-0002-1608-1330 https://orcid.org/0000-0002-6027-042X en_US http://dx.doi.org/10.1021/acs.joc.7b01170 Journal of Organic Chemistry 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) Prof. Swager via Erja Kajosalo |
| spellingShingle | Dengiz, Cagatay Luppino, Sarah Gutierrez, Gregory D. Swager, Timothy M Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes |
| title | Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes |
| title_full | Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes |
| title_fullStr | Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes |
| title_full_unstemmed | Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes |
| title_short | Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes |
| title_sort | naphthazarin polycyclic conjugated hydrocarbons and iptycenes |
| url | http://hdl.handle.net/1721.1/116849 https://orcid.org/0000-0002-1608-1330 https://orcid.org/0000-0002-6027-042X |
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