Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC
A pair of optically active triptycene derivatives ((R,R)- and (S,S)-8) with a distorted cyclic structure were synthesized via an intramolecular etherification and evaluated as a novel chiral selector for high-performance liquid chromatography. The (R,R)- and (S,S)-8-based chiral stationary phases (C...
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| Format: | Article |
| Language: | English |
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Royal Society of Chemistry (RSC)
2020
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| Online Access: | https://hdl.handle.net/1721.1/125403 |
| _version_ | 1826190053242568704 |
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| author | Swager, Timothy M |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Swager, Timothy M |
| author_sort | Swager, Timothy M |
| collection | MIT |
| description | A pair of optically active triptycene derivatives ((R,R)- and (S,S)-8) with a distorted cyclic structure were synthesized via an intramolecular etherification and evaluated as a novel chiral selector for high-performance liquid chromatography. The (R,R)- and (S,S)-8-based chiral stationary phases (CSPs) were found to be particularly effective in the resolution of axially chiral biaryl compounds. The importance of the distorted cyclic structure present in 8 for chiral recognition was demonstrated by comparisons with the corresponding non-cyclic model compound ((R,R)-9), which did not display enantioselectivity in the separation of the test racemates. |
| first_indexed | 2024-09-23T08:34:19Z |
| format | Article |
| id | mit-1721.1/125403 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T08:34:19Z |
| publishDate | 2020 |
| publisher | Royal Society of Chemistry (RSC) |
| record_format | dspace |
| spelling | mit-1721.1/1254032022-09-23T13:01:07Z Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC Swager, Timothy M Massachusetts Institute of Technology. Department of Chemistry A pair of optically active triptycene derivatives ((R,R)- and (S,S)-8) with a distorted cyclic structure were synthesized via an intramolecular etherification and evaluated as a novel chiral selector for high-performance liquid chromatography. The (R,R)- and (S,S)-8-based chiral stationary phases (CSPs) were found to be particularly effective in the resolution of axially chiral biaryl compounds. The importance of the distorted cyclic structure present in 8 for chiral recognition was demonstrated by comparisons with the corresponding non-cyclic model compound ((R,R)-9), which did not display enantioselectivity in the separation of the test racemates. National Science Foundation (U.S.) (Grant DMR-1410718) 2020-05-22T12:23:21Z 2020-05-22T12:23:21Z 2018-06 2020-01-14T13:48:40Z Article http://purl.org/eprint/type/JournalArticle 2046-2069 https://hdl.handle.net/1721.1/125403 Ikai, Tomoyuki et al. “Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC.” RSC advances 8 (2018): 20483-20487 © 2018 The Author(s) en 10.1039/C8RA04434A RSC advances Creative Commons Attribution Noncommercial 3.0 unported license https://creativecommons.org/licenses/by-nc/3.0/ application/pdf Royal Society of Chemistry (RSC) Royal Society of Chemistry (RSC) |
| spellingShingle | Swager, Timothy M Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC |
| title | Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC |
| title_full | Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC |
| title_fullStr | Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC |
| title_full_unstemmed | Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC |
| title_short | Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC |
| title_sort | optically active distorted cyclic triptycenes chiral stationary phases for hplc |
| url | https://hdl.handle.net/1721.1/125403 |
| work_keys_str_mv | AT swagertimothym opticallyactivedistortedcyclictriptyceneschiralstationaryphasesforhplc |