Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality
We report herein the regioselective synthesis of all-carbon lemniscular nanohoops bis-po -CC and bis-pm -TC by the rational control of ring closures at the different positions of planar chiral tetrasubstituted [2.2]paracyclophane. Topological analyses reveal that bis-pm -TC is topologically chiral w...
Gespeichert in:
| Veröffentlicht in: | Chemical science (Cambridge) 2023-04, Vol.14 (16), p.4426-4433 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4433 |
|---|---|
| container_issue | 16 |
| container_start_page | 4426 |
| container_title | Chemical science (Cambridge) |
| container_volume | 14 |
| creator | He, Jing Yu, Mo-Han Lian, Zhe Fan, Yan-Qing Guo, Sheng-Zhu Li, Xiao-Nan Wang, Ying Wang, Wen-Guang Cheng, Zhi-Yun Jiang, Hua |
| description | We report herein the regioselective synthesis of all-carbon lemniscular nanohoops
bis-po
-CC
and
bis-pm
-TC
by the rational control of ring closures at the different positions of planar chiral tetrasubstituted [2.2]paracyclophane. Topological analyses reveal that
bis-pm
-TC
is topologically chiral while
bis-po
-CC
is topologically achiral. X-ray crystal analysis demonstrates that
bis-pm
-TC
adopts a lemniscular conformation with a contiguous conjugation. CD and CPL measurements further reveal that the chiroptical properties of
bis-pm
-TC
are obviously different from those of
bis-po
-CC
due to their different topological chiralities.
We report herein two lemniscular carbon nanohoops
bis-po
-CC
and
bis-pm
-TC
with contiguous conjugation from planar chiral [2.2]paracyclophane, and elucidate the influence of the regioselective synthesis on their topological chirality. |
| doi_str_mv | 10.1039/d2sc06825g |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D2SC06825G</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2805954738</sourcerecordid><originalsourceid>FETCH-LOGICAL-c429t-7bcc26fc508b11c27fa7d19c09c15e813f968293a1fa6d653523521343fd53aa3</originalsourceid><addsrcrecordid>eNpdkk2LFDEQhhtxcZfdvXhXAl5EmDUfk_7wIjLqrjDgQT2JNJnqpDtDOmmT9Mr8Hv-oNc7u-BECKVJP3lTeSlE8ZvSKUdG87HgCWtZc9g-KM06XbFFK0Tw8xpyeFpcpbSkOIZjk1aPiVFSMC1azs-LnWo_eJpidigRU3ARPvPJhCGFK5IfNA4Hgs-3nMKd9uJ17lS1SJoaRTE75_cHBRuXIV37Fv00qKtiBC9OgvH5FrDdu1h40CYbkQZOoexuSdhqyvdUk7TzuJpsIiuYwBRd6C6h2ELV5d1GcGOWSvrxbz4sv7999Xt0s1h-vP6zerBew5E1eVBsAXhqQtN4wBrwyqupYA7QBJnXNhGnQp0YoZlTZoUuS42RiKUwnhVLivHh90J3mzag70D5jAe0U7ajirg3Ktv9mvB3aPty2jDLBuSxR4fmdQgzfZ51yO6K32qFLGv1reU1rvJGWFaLP_kO3YY4e37enZCOXlaiRenGgIIaUojbHahht9_1v3_JPq9_9v0b46d_1H9H7biPw5ADEBMfsnw8kfgHtqrlk</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2805954738</pqid></control><display><type>article</type><title>Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central Open Access</source><source>PubMed Central</source><creator>He, Jing ; Yu, Mo-Han ; Lian, Zhe ; Fan, Yan-Qing ; Guo, Sheng-Zhu ; Li, Xiao-Nan ; Wang, Ying ; Wang, Wen-Guang ; Cheng, Zhi-Yun ; Jiang, Hua</creator><creatorcontrib>He, Jing ; Yu, Mo-Han ; Lian, Zhe ; Fan, Yan-Qing ; Guo, Sheng-Zhu ; Li, Xiao-Nan ; Wang, Ying ; Wang, Wen-Guang ; Cheng, Zhi-Yun ; Jiang, Hua</creatorcontrib><description>We report herein the regioselective synthesis of all-carbon lemniscular nanohoops
bis-po
-CC
and
bis-pm
-TC
by the rational control of ring closures at the different positions of planar chiral tetrasubstituted [2.2]paracyclophane. Topological analyses reveal that
bis-pm
-TC
is topologically chiral while
bis-po
-CC
is topologically achiral. X-ray crystal analysis demonstrates that
bis-pm
-TC
adopts a lemniscular conformation with a contiguous conjugation. CD and CPL measurements further reveal that the chiroptical properties of
bis-pm
-TC
are obviously different from those of
bis-po
-CC
due to their different topological chiralities.
We report herein two lemniscular carbon nanohoops
bis-po
-CC
and
bis-pm
-TC
with contiguous conjugation from planar chiral [2.2]paracyclophane, and elucidate the influence of the regioselective synthesis on their topological chirality.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d2sc06825g</identifier><identifier>PMID: 37123181</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Carbon ; Chemistry ; Chirality ; Conjugation ; Regioselectivity ; Synthesis ; Topology</subject><ispartof>Chemical science (Cambridge), 2023-04, Vol.14 (16), p.4426-4433</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2023</rights><rights>This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-7bcc26fc508b11c27fa7d19c09c15e813f968293a1fa6d653523521343fd53aa3</citedby><cites>FETCH-LOGICAL-c429t-7bcc26fc508b11c27fa7d19c09c15e813f968293a1fa6d653523521343fd53aa3</cites><orcidid>0000-0002-4108-7865 ; 0000-0002-9917-2683 ; 0000-0002-7015-7228</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10132256/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10132256/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,315,728,781,785,865,886,27929,27930,53796,53798</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37123181$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>He, Jing</creatorcontrib><creatorcontrib>Yu, Mo-Han</creatorcontrib><creatorcontrib>Lian, Zhe</creatorcontrib><creatorcontrib>Fan, Yan-Qing</creatorcontrib><creatorcontrib>Guo, Sheng-Zhu</creatorcontrib><creatorcontrib>Li, Xiao-Nan</creatorcontrib><creatorcontrib>Wang, Ying</creatorcontrib><creatorcontrib>Wang, Wen-Guang</creatorcontrib><creatorcontrib>Cheng, Zhi-Yun</creatorcontrib><creatorcontrib>Jiang, Hua</creatorcontrib><title>Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>We report herein the regioselective synthesis of all-carbon lemniscular nanohoops
bis-po
-CC
and
bis-pm
-TC
by the rational control of ring closures at the different positions of planar chiral tetrasubstituted [2.2]paracyclophane. Topological analyses reveal that
bis-pm
-TC
is topologically chiral while
bis-po
-CC
is topologically achiral. X-ray crystal analysis demonstrates that
bis-pm
-TC
adopts a lemniscular conformation with a contiguous conjugation. CD and CPL measurements further reveal that the chiroptical properties of
bis-pm
-TC
are obviously different from those of
bis-po
-CC
due to their different topological chiralities.
We report herein two lemniscular carbon nanohoops
bis-po
-CC
and
bis-pm
-TC
with contiguous conjugation from planar chiral [2.2]paracyclophane, and elucidate the influence of the regioselective synthesis on their topological chirality.</description><subject>Carbon</subject><subject>Chemistry</subject><subject>Chirality</subject><subject>Conjugation</subject><subject>Regioselectivity</subject><subject>Synthesis</subject><subject>Topology</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkk2LFDEQhhtxcZfdvXhXAl5EmDUfk_7wIjLqrjDgQT2JNJnqpDtDOmmT9Mr8Hv-oNc7u-BECKVJP3lTeSlE8ZvSKUdG87HgCWtZc9g-KM06XbFFK0Tw8xpyeFpcpbSkOIZjk1aPiVFSMC1azs-LnWo_eJpidigRU3ARPvPJhCGFK5IfNA4Hgs-3nMKd9uJ17lS1SJoaRTE75_cHBRuXIV37Fv00qKtiBC9OgvH5FrDdu1h40CYbkQZOoexuSdhqyvdUk7TzuJpsIiuYwBRd6C6h2ELV5d1GcGOWSvrxbz4sv7999Xt0s1h-vP6zerBew5E1eVBsAXhqQtN4wBrwyqupYA7QBJnXNhGnQp0YoZlTZoUuS42RiKUwnhVLivHh90J3mzag70D5jAe0U7ajirg3Ktv9mvB3aPty2jDLBuSxR4fmdQgzfZ51yO6K32qFLGv1reU1rvJGWFaLP_kO3YY4e37enZCOXlaiRenGgIIaUojbHahht9_1v3_JPq9_9v0b46d_1H9H7biPw5ADEBMfsnw8kfgHtqrlk</recordid><startdate>20230426</startdate><enddate>20230426</enddate><creator>He, Jing</creator><creator>Yu, Mo-Han</creator><creator>Lian, Zhe</creator><creator>Fan, Yan-Qing</creator><creator>Guo, Sheng-Zhu</creator><creator>Li, Xiao-Nan</creator><creator>Wang, Ying</creator><creator>Wang, Wen-Guang</creator><creator>Cheng, Zhi-Yun</creator><creator>Jiang, Hua</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-4108-7865</orcidid><orcidid>https://orcid.org/0000-0002-9917-2683</orcidid><orcidid>https://orcid.org/0000-0002-7015-7228</orcidid></search><sort><creationdate>20230426</creationdate><title>Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality</title><author>He, Jing ; Yu, Mo-Han ; Lian, Zhe ; Fan, Yan-Qing ; Guo, Sheng-Zhu ; Li, Xiao-Nan ; Wang, Ying ; Wang, Wen-Guang ; Cheng, Zhi-Yun ; Jiang, Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-7bcc26fc508b11c27fa7d19c09c15e813f968293a1fa6d653523521343fd53aa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Carbon</topic><topic>Chemistry</topic><topic>Chirality</topic><topic>Conjugation</topic><topic>Regioselectivity</topic><topic>Synthesis</topic><topic>Topology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Jing</creatorcontrib><creatorcontrib>Yu, Mo-Han</creatorcontrib><creatorcontrib>Lian, Zhe</creatorcontrib><creatorcontrib>Fan, Yan-Qing</creatorcontrib><creatorcontrib>Guo, Sheng-Zhu</creatorcontrib><creatorcontrib>Li, Xiao-Nan</creatorcontrib><creatorcontrib>Wang, Ying</creatorcontrib><creatorcontrib>Wang, Wen-Guang</creatorcontrib><creatorcontrib>Cheng, Zhi-Yun</creatorcontrib><creatorcontrib>Jiang, Hua</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>He, Jing</au><au>Yu, Mo-Han</au><au>Lian, Zhe</au><au>Fan, Yan-Qing</au><au>Guo, Sheng-Zhu</au><au>Li, Xiao-Nan</au><au>Wang, Ying</au><au>Wang, Wen-Guang</au><au>Cheng, Zhi-Yun</au><au>Jiang, Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2023-04-26</date><risdate>2023</risdate><volume>14</volume><issue>16</issue><spage>4426</spage><epage>4433</epage><pages>4426-4433</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>We report herein the regioselective synthesis of all-carbon lemniscular nanohoops
bis-po
-CC
and
bis-pm
-TC
by the rational control of ring closures at the different positions of planar chiral tetrasubstituted [2.2]paracyclophane. Topological analyses reveal that
bis-pm
-TC
is topologically chiral while
bis-po
-CC
is topologically achiral. X-ray crystal analysis demonstrates that
bis-pm
-TC
adopts a lemniscular conformation with a contiguous conjugation. CD and CPL measurements further reveal that the chiroptical properties of
bis-pm
-TC
are obviously different from those of
bis-po
-CC
due to their different topological chiralities.
We report herein two lemniscular carbon nanohoops
bis-po
-CC
and
bis-pm
-TC
with contiguous conjugation from planar chiral [2.2]paracyclophane, and elucidate the influence of the regioselective synthesis on their topological chirality.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37123181</pmid><doi>10.1039/d2sc06825g</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-4108-7865</orcidid><orcidid>https://orcid.org/0000-0002-9917-2683</orcidid><orcidid>https://orcid.org/0000-0002-7015-7228</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2023-04, Vol.14 (16), p.4426-4433 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D2SC06825G |
| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Carbon Chemistry Chirality Conjugation Regioselectivity Synthesis Topology |
| title | Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-15T08%3A11%3A33IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Lemniscular%20carbon%20nanohoops%20with%20contiguous%20conjugation%20from%20planar%20chiral%20%5B2.2%5Dparacyclophane:%20influence%20of%20the%20regioselective%20synthesis%20on%20topological%20chirality&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=He,%20Jing&rft.date=2023-04-26&rft.volume=14&rft.issue=16&rft.spage=4426&rft.epage=4433&rft.pages=4426-4433&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/d2sc06825g&rft_dat=%3Cproquest_cross%3E2805954738%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2805954738&rft_id=info:pmid/37123181&rfr_iscdi=true |