Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores
The high yielding Cu I -mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the Cu I catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report...
Gespeichert in:
| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-07, Vol.56 (54), p.7447-745 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 745 |
|---|---|
| container_issue | 54 |
| container_start_page | 7447 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 56 |
| creator | Ngo, Huynh Thien Lewis, James E. M Payne, Daniel T D'Souza, Francis Hill, Jonathan P Ariga, Katsuhiko Yoshikawa, Genki Goldup, Stephen M |
| description | The high yielding Cu
I
-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the Cu
I
catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane" strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing Cu
I
-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.
Rotaxane as sacrificial template to avoid metal insertion in porphyrinoids during copper catalyzed click reaction. |
| doi_str_mv | 10.1039/c9cc09681g |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_proquest_miscellaneous_2409640698</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2409640698</sourcerecordid><originalsourceid>FETCH-LOGICAL-c376t-f28e8458b5b296a6ef802403c86ffc3f43b97f268809424863022ccf51e39e7b3</originalsourceid><addsrcrecordid>eNp9kUtLAzEQxxdR8HnxLkS8iLCazavJURatgiCIgrclTSdt6m6yJlvQb2_aioIH5zAzML_5M4-iOK7wZYWpujLKGKyErGZbxV5FBSs5k6_bq5yrckQZ3y32U1rgbBWXe8XbUxj0h_Z6cMEjnZBGCd6XkAaIzs_QAF3f6gHQEFAfwbTLKSDnjZuCH3SLOlh55xPEtYLzyITcAh8otG4WzDyGLvTzECEdFjtWtwmOvuNB8XJ781zflQ-P4_v6-qE0dCSG0hIJknE54ROihBZgJSYMUyOFtYZaRidqZImQEitGmBQUE2KM5RVQBaMJPSjON7p9DOtVms4lA22rPYRlarKYEgwLJTN69gddhGX0ebpMEcwprwjJ1MWGMjGkFME2fXSdjp9NhZvV3Zta1fX67uMMn2zgmMwP9_uXXD_9r970U0u_AF6zi_0</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2420535122</pqid></control><display><type>article</type><title>Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Ngo, Huynh Thien ; Lewis, James E. M ; Payne, Daniel T ; D'Souza, Francis ; Hill, Jonathan P ; Ariga, Katsuhiko ; Yoshikawa, Genki ; Goldup, Stephen M</creator><creatorcontrib>Ngo, Huynh Thien ; Lewis, James E. M ; Payne, Daniel T ; D'Souza, Francis ; Hill, Jonathan P ; Ariga, Katsuhiko ; Yoshikawa, Genki ; Goldup, Stephen M</creatorcontrib><description>The high yielding Cu
I
-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the Cu
I
catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane" strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing Cu
I
-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.
Rotaxane as sacrificial template to avoid metal insertion in porphyrinoids during copper catalyzed click reaction.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc09681g</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Cations ; Coordination compounds ; Copper ; Insertion ; Porphyrins ; Rotaxanes ; Sequestering</subject><ispartof>Chemical communications (Cambridge, England), 2020-07, Vol.56 (54), p.7447-745</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c376t-f28e8458b5b296a6ef802403c86ffc3f43b97f268809424863022ccf51e39e7b3</citedby><cites>FETCH-LOGICAL-c376t-f28e8458b5b296a6ef802403c86ffc3f43b97f268809424863022ccf51e39e7b3</cites><orcidid>0000-0002-0844-316X ; 0000-0001-5571-3452 ; 0000-0001-7707-8381 ; 0000-0003-3815-8949 ; 0000-0002-4229-5842 ; 0000-0003-3781-0464 ; 0000-0002-2445-2955 ; 0000-0002-9136-8964</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Ngo, Huynh Thien</creatorcontrib><creatorcontrib>Lewis, James E. M</creatorcontrib><creatorcontrib>Payne, Daniel T</creatorcontrib><creatorcontrib>D'Souza, Francis</creatorcontrib><creatorcontrib>Hill, Jonathan P</creatorcontrib><creatorcontrib>Ariga, Katsuhiko</creatorcontrib><creatorcontrib>Yoshikawa, Genki</creatorcontrib><creatorcontrib>Goldup, Stephen M</creatorcontrib><title>Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores</title><title>Chemical communications (Cambridge, England)</title><description>The high yielding Cu
I
-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the Cu
I
catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane" strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing Cu
I
-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.
Rotaxane as sacrificial template to avoid metal insertion in porphyrinoids during copper catalyzed click reaction.</description><subject>Cations</subject><subject>Coordination compounds</subject><subject>Copper</subject><subject>Insertion</subject><subject>Porphyrins</subject><subject>Rotaxanes</subject><subject>Sequestering</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kUtLAzEQxxdR8HnxLkS8iLCazavJURatgiCIgrclTSdt6m6yJlvQb2_aioIH5zAzML_5M4-iOK7wZYWpujLKGKyErGZbxV5FBSs5k6_bq5yrckQZ3y32U1rgbBWXe8XbUxj0h_Z6cMEjnZBGCd6XkAaIzs_QAF3f6gHQEFAfwbTLKSDnjZuCH3SLOlh55xPEtYLzyITcAh8otG4WzDyGLvTzECEdFjtWtwmOvuNB8XJ781zflQ-P4_v6-qE0dCSG0hIJknE54ROihBZgJSYMUyOFtYZaRidqZImQEitGmBQUE2KM5RVQBaMJPSjON7p9DOtVms4lA22rPYRlarKYEgwLJTN69gddhGX0ebpMEcwprwjJ1MWGMjGkFME2fXSdjp9NhZvV3Zta1fX67uMMn2zgmMwP9_uXXD_9r970U0u_AF6zi_0</recordid><startdate>20200711</startdate><enddate>20200711</enddate><creator>Ngo, Huynh Thien</creator><creator>Lewis, James E. M</creator><creator>Payne, Daniel T</creator><creator>D'Souza, Francis</creator><creator>Hill, Jonathan P</creator><creator>Ariga, Katsuhiko</creator><creator>Yoshikawa, Genki</creator><creator>Goldup, Stephen M</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0844-316X</orcidid><orcidid>https://orcid.org/0000-0001-5571-3452</orcidid><orcidid>https://orcid.org/0000-0001-7707-8381</orcidid><orcidid>https://orcid.org/0000-0003-3815-8949</orcidid><orcidid>https://orcid.org/0000-0002-4229-5842</orcidid><orcidid>https://orcid.org/0000-0003-3781-0464</orcidid><orcidid>https://orcid.org/0000-0002-2445-2955</orcidid><orcidid>https://orcid.org/0000-0002-9136-8964</orcidid></search><sort><creationdate>20200711</creationdate><title>Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores</title><author>Ngo, Huynh Thien ; Lewis, James E. M ; Payne, Daniel T ; D'Souza, Francis ; Hill, Jonathan P ; Ariga, Katsuhiko ; Yoshikawa, Genki ; Goldup, Stephen M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c376t-f28e8458b5b296a6ef802403c86ffc3f43b97f268809424863022ccf51e39e7b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Cations</topic><topic>Coordination compounds</topic><topic>Copper</topic><topic>Insertion</topic><topic>Porphyrins</topic><topic>Rotaxanes</topic><topic>Sequestering</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ngo, Huynh Thien</creatorcontrib><creatorcontrib>Lewis, James E. M</creatorcontrib><creatorcontrib>Payne, Daniel T</creatorcontrib><creatorcontrib>D'Souza, Francis</creatorcontrib><creatorcontrib>Hill, Jonathan P</creatorcontrib><creatorcontrib>Ariga, Katsuhiko</creatorcontrib><creatorcontrib>Yoshikawa, Genki</creatorcontrib><creatorcontrib>Goldup, Stephen M</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ngo, Huynh Thien</au><au>Lewis, James E. M</au><au>Payne, Daniel T</au><au>D'Souza, Francis</au><au>Hill, Jonathan P</au><au>Ariga, Katsuhiko</au><au>Yoshikawa, Genki</au><au>Goldup, Stephen M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2020-07-11</date><risdate>2020</risdate><volume>56</volume><issue>54</issue><spage>7447</spage><epage>745</epage><pages>7447-745</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The high yielding Cu
I
-mediated click reaction is an effective procedure for the preparation of oligoporphyrinoid conjugates. However, the Cu
I
catalyst leads to the adventitious and usually undesirable insertion of Cu ions into any non-metalated porphyrinoid centers during reaction. Here we report a "sacrificial rotaxane" strategy for the multifunctionalization of porphyrins with free base corroles without incidental copper insertion. This strategy can be considered a general method for implementing Cu
I
-mediated click reactions with metal cation sequestration to avoid detrimental effects caused by the presence of copper cations.
Rotaxane as sacrificial template to avoid metal insertion in porphyrinoids during copper catalyzed click reaction.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c9cc09681g</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-0844-316X</orcidid><orcidid>https://orcid.org/0000-0001-5571-3452</orcidid><orcidid>https://orcid.org/0000-0001-7707-8381</orcidid><orcidid>https://orcid.org/0000-0003-3815-8949</orcidid><orcidid>https://orcid.org/0000-0002-4229-5842</orcidid><orcidid>https://orcid.org/0000-0003-3781-0464</orcidid><orcidid>https://orcid.org/0000-0002-2445-2955</orcidid><orcidid>https://orcid.org/0000-0002-9136-8964</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-07, Vol.56 (54), p.7447-745 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2409640698 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Cations Coordination compounds Copper Insertion Porphyrins Rotaxanes Sequestering |
| title | Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-11T01%3A54%3A09IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_rsc_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Rotaxanation%20as%20a%20sequestering%20template%20to%20preclude%20incidental%20metal%20insertion%20in%20complex%20oligochromophores&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Ngo,%20Huynh%20Thien&rft.date=2020-07-11&rft.volume=56&rft.issue=54&rft.spage=7447&rft.epage=745&rft.pages=7447-745&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/c9cc09681g&rft_dat=%3Cproquest_rsc_p%3E2409640698%3C/proquest_rsc_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2420535122&rft_id=info:pmid/&rfr_iscdi=true |