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N -Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State
Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane ( ) including one pair of enantiomers ( ) and one meso isomer ( ) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state showed heterochiral self-sorting behavior along axis with cofa...
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| Published in: | Frontiers in chemistry 2019-05, Vol.7, p.383-383 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| container_end_page | 383 |
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| container_start_page | 383 |
| container_title | Frontiers in chemistry |
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| creator | Chen, Yuan Cheng, Ming Hong, Benkun Zhao, Qian Qian, Cheng Jiang, Juli Li, Shuhua Lin, Chen Wang, Leyong |
| description | Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane
(
) including one pair of enantiomers (
) and one meso isomer (
) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state
showed heterochiral self-sorting behavior along
axis with cofacial π
π stacking interactions, while
showed heterochiral self-sorting behavior along
axis with slipped π-π stacking interactions, respectively. Meanwhile both of them showed homochiral self-sorting behavior along
axis as well as one pair of supramolecular helixes were formed in both cases. All the self-sorting behaviors are controlled by two chiral Tröger's Base units from neighboring molecules. To the best of our knowledge, such chiral self-sorting and supramolecular helixes of
-centered chiral superstructures is a rare example. In addition,
and
demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively. |
| doi_str_mv | 10.3389/fchem.2019.00383 |
| format | article |
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(
) including one pair of enantiomers (
) and one meso isomer (
) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state
showed heterochiral self-sorting behavior along
axis with cofacial π
π stacking interactions, while
showed heterochiral self-sorting behavior along
axis with slipped π-π stacking interactions, respectively. Meanwhile both of them showed homochiral self-sorting behavior along
axis as well as one pair of supramolecular helixes were formed in both cases. All the self-sorting behaviors are controlled by two chiral Tröger's Base units from neighboring molecules. To the best of our knowledge, such chiral self-sorting and supramolecular helixes of
-centered chiral superstructures is a rare example. In addition,
and
demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively.</description><identifier>ISSN: 2296-2646</identifier><identifier>EISSN: 2296-2646</identifier><identifier>DOI: 10.3389/fchem.2019.00383</identifier><identifier>PMID: 31214566</identifier><language>eng</language><publisher>Switzerland: Frontiers Media S.A</publisher><subject>Chemistry ; chiral self-sorting ; gas adsorption ; N-centered chirality ; supramolecular helix ; tröger's base</subject><ispartof>Frontiers in chemistry, 2019-05, Vol.7, p.383-383</ispartof><rights>Copyright © 2019 Chen, Cheng, Hong, Zhao, Qian, Jiang, Li, Lin and Wang. 2019 Chen, Cheng, Hong, Zhao, Qian, Jiang, Li, Lin and Wang</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c528t-63314b17ede2591f8566dbc02ed5adac317be36353660ce380265d725afc0c5a3</citedby><cites>FETCH-LOGICAL-c528t-63314b17ede2591f8566dbc02ed5adac317be36353660ce380265d725afc0c5a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6555195/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6555195/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31214566$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Yuan</creatorcontrib><creatorcontrib>Cheng, Ming</creatorcontrib><creatorcontrib>Hong, Benkun</creatorcontrib><creatorcontrib>Zhao, Qian</creatorcontrib><creatorcontrib>Qian, Cheng</creatorcontrib><creatorcontrib>Jiang, Juli</creatorcontrib><creatorcontrib>Li, Shuhua</creatorcontrib><creatorcontrib>Lin, Chen</creatorcontrib><creatorcontrib>Wang, Leyong</creatorcontrib><title>N -Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State</title><title>Frontiers in chemistry</title><addtitle>Front Chem</addtitle><description>Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane
(
) including one pair of enantiomers (
) and one meso isomer (
) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state
showed heterochiral self-sorting behavior along
axis with cofacial π
π stacking interactions, while
showed heterochiral self-sorting behavior along
axis with slipped π-π stacking interactions, respectively. Meanwhile both of them showed homochiral self-sorting behavior along
axis as well as one pair of supramolecular helixes were formed in both cases. All the self-sorting behaviors are controlled by two chiral Tröger's Base units from neighboring molecules. To the best of our knowledge, such chiral self-sorting and supramolecular helixes of
-centered chiral superstructures is a rare example. In addition,
and
demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively.</description><subject>Chemistry</subject><subject>chiral self-sorting</subject><subject>gas adsorption</subject><subject>N-centered chirality</subject><subject>supramolecular helix</subject><subject>tröger's base</subject><issn>2296-2646</issn><issn>2296-2646</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>DOA</sourceid><recordid>eNpVks9u1DAQxiMEolXpnRPyDS5ZbE_sJBckCH9aqcBhy9ly7PGuKydZ7CxiX6wv0BfDu1uq9mKP7JnfjD9_RfGa0QVA0753Zo3DglPWLiiFBp4Vp5y3suSyks8fxSfFeUo3lFLGGVScvixOIIeVkPK02P0gZYfjjBEt6dY-6kCWGFy5nOLsxxXRoyXL7SbqYQpotkFHcoHB_yWTI9fx7naF8W0in3TCcr9Y8tkPGL0h37WJk9mZgIn4kXRxl2Ydgh-RLGc946vihdMh4fn9flb8-vrlursor35-u-w-XpVG8GYuJQCrelajRS5a5po8tu0N5WiFttoAq3sECQKkpAahoVwKW3OhnaFGaDgrLo9cO-kbtYl-0HGnJu3V4WCKK6XzU_OcyjQWDVgLvdNVQ0HXsq3BGGYdVo7vWR-OrM22H9CaLFwW7An06c3o12o1_VFSCMFakQHv7gFx-r3FNKvBJ4Mh6BGnbVKcV1A1VQt1TqXH1CxjShHdQxtG1d4A6mAAtTeAOhggl7x5PN5Dwf_vhn-dTa9K</recordid><startdate>20190531</startdate><enddate>20190531</enddate><creator>Chen, Yuan</creator><creator>Cheng, Ming</creator><creator>Hong, Benkun</creator><creator>Zhao, Qian</creator><creator>Qian, Cheng</creator><creator>Jiang, Juli</creator><creator>Li, Shuhua</creator><creator>Lin, Chen</creator><creator>Wang, Leyong</creator><general>Frontiers Media S.A</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20190531</creationdate><title>N -Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State</title><author>Chen, Yuan ; Cheng, Ming ; Hong, Benkun ; Zhao, Qian ; Qian, Cheng ; Jiang, Juli ; Li, Shuhua ; Lin, Chen ; Wang, Leyong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c528t-63314b17ede2591f8566dbc02ed5adac317be36353660ce380265d725afc0c5a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Chemistry</topic><topic>chiral self-sorting</topic><topic>gas adsorption</topic><topic>N-centered chirality</topic><topic>supramolecular helix</topic><topic>tröger's base</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Yuan</creatorcontrib><creatorcontrib>Cheng, Ming</creatorcontrib><creatorcontrib>Hong, Benkun</creatorcontrib><creatorcontrib>Zhao, Qian</creatorcontrib><creatorcontrib>Qian, Cheng</creatorcontrib><creatorcontrib>Jiang, Juli</creatorcontrib><creatorcontrib>Li, Shuhua</creatorcontrib><creatorcontrib>Lin, Chen</creatorcontrib><creatorcontrib>Wang, Leyong</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Frontiers in chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Yuan</au><au>Cheng, Ming</au><au>Hong, Benkun</au><au>Zhao, Qian</au><au>Qian, Cheng</au><au>Jiang, Juli</au><au>Li, Shuhua</au><au>Lin, Chen</au><au>Wang, Leyong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N -Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State</atitle><jtitle>Frontiers in chemistry</jtitle><addtitle>Front Chem</addtitle><date>2019-05-31</date><risdate>2019</risdate><volume>7</volume><spage>383</spage><epage>383</epage><pages>383-383</pages><issn>2296-2646</issn><eissn>2296-2646</eissn><abstract>Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane
(
) including one pair of enantiomers (
) and one meso isomer (
) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state
showed heterochiral self-sorting behavior along
axis with cofacial π
π stacking interactions, while
showed heterochiral self-sorting behavior along
axis with slipped π-π stacking interactions, respectively. Meanwhile both of them showed homochiral self-sorting behavior along
axis as well as one pair of supramolecular helixes were formed in both cases. All the self-sorting behaviors are controlled by two chiral Tröger's Base units from neighboring molecules. To the best of our knowledge, such chiral self-sorting and supramolecular helixes of
-centered chiral superstructures is a rare example. In addition,
and
demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively.</abstract><cop>Switzerland</cop><pub>Frontiers Media S.A</pub><pmid>31214566</pmid><doi>10.3389/fchem.2019.00383</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | PubMed (Medline) |
| subjects | Chemistry chiral self-sorting gas adsorption N-centered chirality supramolecular helix tröger's base |
| title | N -Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State |
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