Triptycene-Based Ladder Polymers with One-Handed Helical Geometry
Here we report an efficient synthesis of optically active ladder-type molecules and polymers through intramolecular cyclization of chiral triptycenes containing bis[2-(4-alkoxyphenyl)ethynyl]phenylene units. The electrophile-induced cyclization reactions are directed away from the bridgehead carbon...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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American Chemical Society (ACS)
2020
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| Online Access: | https://hdl.handle.net/1721.1/128144 |
| _version_ | 1811083383548149760 |
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| author | Ikai, Tomoyuki Yoshida, Takumu Shinohara, Ken-ichi Taniguchi, Tsuyoshi Wada, Yuya Swager, Timothy M |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Ikai, Tomoyuki Yoshida, Takumu Shinohara, Ken-ichi Taniguchi, Tsuyoshi Wada, Yuya Swager, Timothy M |
| author_sort | Ikai, Tomoyuki |
| collection | MIT |
| description | Here we report an efficient synthesis of optically active ladder-type molecules and polymers through intramolecular cyclization of chiral triptycenes containing bis[2-(4-alkoxyphenyl)ethynyl]phenylene units. The electrophile-induced cyclization reactions are directed away from the bridgehead carbon atoms of triptycene by steric factors, thereby producing one-handed twisted ladder units without any detectable byproducts. Moreover, the quantitative and regioselective nature of this intramolecular cyclization allowed us to synthesize optically active ladder polymers with a well-defined one-handed helical geometry in which homoconjugated dibenzo[a,h]anthracene units are helically arranged along the main chain. This synthesis route enables the construction of a variety of nanoscale helical ladder architectures and provides an entry into new chiroptical materials. |
| first_indexed | 2024-09-23T12:32:11Z |
| format | Article |
| id | mit-1721.1/128144 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T12:32:11Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1281442022-09-28T08:23:59Z Triptycene-Based Ladder Polymers with One-Handed Helical Geometry Ikai, Tomoyuki Yoshida, Takumu Shinohara, Ken-ichi Taniguchi, Tsuyoshi Wada, Yuya Swager, Timothy M Massachusetts Institute of Technology. Department of Chemistry Here we report an efficient synthesis of optically active ladder-type molecules and polymers through intramolecular cyclization of chiral triptycenes containing bis[2-(4-alkoxyphenyl)ethynyl]phenylene units. The electrophile-induced cyclization reactions are directed away from the bridgehead carbon atoms of triptycene by steric factors, thereby producing one-handed twisted ladder units without any detectable byproducts. Moreover, the quantitative and regioselective nature of this intramolecular cyclization allowed us to synthesize optically active ladder polymers with a well-defined one-handed helical geometry in which homoconjugated dibenzo[a,h]anthracene units are helically arranged along the main chain. This synthesis route enables the construction of a variety of nanoscale helical ladder architectures and provides an entry into new chiroptical materials. Air Force Office of Scientific Research (Grant 17RT0904) 2020-10-22T16:12:52Z 2020-10-22T16:12:52Z 2019-02 2018-12 2020-10-07T18:33:38Z Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 https://hdl.handle.net/1721.1/128144 Ikai, Tomoyuki et al. "Triptycene-Based Ladder Polymers with One-Handed Helical Geometry." Journal of the American Chemical Society 141, 11 (February 2019): 4696–4703 © 2019 American Chemical Society en http://dx.doi.org/10.1021/jacs.8b13865 Journal of the American Chemical Society 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 Ye Li |
| spellingShingle | Ikai, Tomoyuki Yoshida, Takumu Shinohara, Ken-ichi Taniguchi, Tsuyoshi Wada, Yuya Swager, Timothy M Triptycene-Based Ladder Polymers with One-Handed Helical Geometry |
| title | Triptycene-Based Ladder Polymers with One-Handed Helical Geometry |
| title_full | Triptycene-Based Ladder Polymers with One-Handed Helical Geometry |
| title_fullStr | Triptycene-Based Ladder Polymers with One-Handed Helical Geometry |
| title_full_unstemmed | Triptycene-Based Ladder Polymers with One-Handed Helical Geometry |
| title_short | Triptycene-Based Ladder Polymers with One-Handed Helical Geometry |
| title_sort | triptycene based ladder polymers with one handed helical geometry |
| url | https://hdl.handle.net/1721.1/128144 |
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