Molecular Basis for the Recognition of Higher Fullerenes into Ureidopyrimidinone-Cyclotriveratrylene Self-Assembled Capsules
Fullerenes C60, C70, and C84 may be readily encaged within a hydrogen‐bonded dimeric capsule, based on two concave cyclotriveratrylene (CTV) scaffolds, each containing three self‐complementary 2‐ureido‐4‐[1H]‐pyrimidinone (UPy) subunits. NMR spectroscopy and circular dichroism studies, complemented...
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| Veröffentlicht in: | Chemistry : a European journal 2016-09, Vol.22 (38), p.13496-13505 |
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| creator | Huerta, Elisa Serapian, Stefano Artin Santos, Eva Cequier, Enrique Bo, Carles de Mendoza, Javier |
| description | Fullerenes C60, C70, and C84 may be readily encaged within a hydrogen‐bonded dimeric capsule, based on two concave cyclotriveratrylene (CTV) scaffolds, each containing three self‐complementary 2‐ureido‐4‐[1H]‐pyrimidinone (UPy) subunits. NMR spectroscopy and circular dichroism studies, complemented by dispersion‐corrected DFT calculations, are reported with the aim of characterizing such capsule–fullerene complexes both structurally and energetically. Six fullerenes are considered: in agreement with experiments, calculations find that encapsulation is most favorable for C84 (on a par with C90), and follows the trend C60 |
| doi_str_mv | 10.1002/chem.201601690 |
| format | Article |
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Catch a fullerene! Supramolecular dimeric capsules (see figure), based on cyclotriveratrylene equipped with self‐complementary ureidopyrimidinone moieties, show selectivity towards C84 and C70 over C60. Combining theory and experiment, the molecular basis of such selectivity is explored.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201601690</identifier><identifier>PMID: 27405088</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Buckminsterfullerene ; Chemistry ; circular dichroism ; density functional calculations ; Encapsulation ; Ethylene ; Fullerenes ; host-guest systems ; Mathematical analysis ; NMR spectroscopy ; Selectivity ; Spectrum analysis ; Trends</subject><ispartof>Chemistry : a European journal, 2016-09, Vol.22 (38), p.13496-13505</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5210-85ae10a38eeb43718613ba77471d0f818a764921915ebc262d0f231286e37e843</citedby><cites>FETCH-LOGICAL-c5210-85ae10a38eeb43718613ba77471d0f818a764921915ebc262d0f231286e37e843</cites><orcidid>0000-0001-9581-2922 ; 0000-0003-0122-8499</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201601690$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201601690$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27405088$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huerta, Elisa</creatorcontrib><creatorcontrib>Serapian, Stefano Artin</creatorcontrib><creatorcontrib>Santos, Eva</creatorcontrib><creatorcontrib>Cequier, Enrique</creatorcontrib><creatorcontrib>Bo, Carles</creatorcontrib><creatorcontrib>de Mendoza, Javier</creatorcontrib><title>Molecular Basis for the Recognition of Higher Fullerenes into Ureidopyrimidinone-Cyclotriveratrylene Self-Assembled Capsules</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Fullerenes C60, C70, and C84 may be readily encaged within a hydrogen‐bonded dimeric capsule, based on two concave cyclotriveratrylene (CTV) scaffolds, each containing three self‐complementary 2‐ureido‐4‐[1H]‐pyrimidinone (UPy) subunits. NMR spectroscopy and circular dichroism studies, complemented by dispersion‐corrected DFT calculations, are reported with the aim of characterizing such capsule–fullerene complexes both structurally and energetically. Six fullerenes are considered: in agreement with experiments, calculations find that encapsulation is most favorable for C84 (on a par with C90), and follows the trend C60<C70<C76<C78<C84≈C90. As also found by NMR spectroscopy, the most stable capsules are formed by monomers of identical stereochemistry with UPy and the OMe groups of CTV in a mutual anti orientation and UPy–CTV ethylene linkers within the capsular surface plane. Up to C78, encapsulation is favored by increasing host–guest contacts, but the trend is thereafter increasingly inhibited by growing capsule strain.
Catch a fullerene! Supramolecular dimeric capsules (see figure), based on cyclotriveratrylene equipped with self‐complementary ureidopyrimidinone moieties, show selectivity towards C84 and C70 over C60. Combining theory and experiment, the molecular basis of such selectivity is explored.</description><subject>Buckminsterfullerene</subject><subject>Chemistry</subject><subject>circular dichroism</subject><subject>density functional calculations</subject><subject>Encapsulation</subject><subject>Ethylene</subject><subject>Fullerenes</subject><subject>host-guest systems</subject><subject>Mathematical analysis</subject><subject>NMR spectroscopy</subject><subject>Selectivity</subject><subject>Spectrum analysis</subject><subject>Trends</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqNkd9r1TAYhoMo7mx666UEvPGmx_xok_Rylm0VNgXn0LuQtl93MtPmmLS6gn-8OZx5EG8UAh-E533g-16EXlCypoSwN-0GhjUjVKRXkkdoRQtGMy5F8RitSJnLTBS8PELHMd4RQkrB-VN0xGROCqLUCv288g7a2ZmA35poI-59wNMG8Edo_e1oJ-tH7Htc29sNBHw-OwcBRojYjpPHNwFs57dLsIPt7OhHyKqldX4K9jsEM4XFJRhfg-uz0xhhaBx0uDLbODuIz9CT3rgIzx_mCbo5P_tU1dnlh4t31ell1qZlSKYKA5QYrgCanEuqBOWNkTKXtCO9ospIkZeMlrSApmWCpV_GKVMCuASV8xP0eu_dBv9thjjpwcYWnDMj-DlqqnghiCpJ-R8olcmYzpfQV3-hd34OY1pkRwklZK52wvWeaoOPMUCvt-lYJiyaEr2rUO8q1IcKU-Dlg3ZuBugO-O_OElDugR_WwfIPna7qs6s_5dk-a-ME94esCV-1kFwW-vP7C31dfSlZTmtd81-MU7cR</recordid><startdate>20160912</startdate><enddate>20160912</enddate><creator>Huerta, Elisa</creator><creator>Serapian, Stefano Artin</creator><creator>Santos, Eva</creator><creator>Cequier, Enrique</creator><creator>Bo, Carles</creator><creator>de Mendoza, Javier</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9581-2922</orcidid><orcidid>https://orcid.org/0000-0003-0122-8499</orcidid></search><sort><creationdate>20160912</creationdate><title>Molecular Basis for the Recognition of Higher Fullerenes into Ureidopyrimidinone-Cyclotriveratrylene Self-Assembled Capsules</title><author>Huerta, Elisa ; Serapian, Stefano Artin ; Santos, Eva ; Cequier, Enrique ; Bo, Carles ; de Mendoza, Javier</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5210-85ae10a38eeb43718613ba77471d0f818a764921915ebc262d0f231286e37e843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Buckminsterfullerene</topic><topic>Chemistry</topic><topic>circular dichroism</topic><topic>density functional calculations</topic><topic>Encapsulation</topic><topic>Ethylene</topic><topic>Fullerenes</topic><topic>host-guest systems</topic><topic>Mathematical analysis</topic><topic>NMR spectroscopy</topic><topic>Selectivity</topic><topic>Spectrum analysis</topic><topic>Trends</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huerta, Elisa</creatorcontrib><creatorcontrib>Serapian, Stefano Artin</creatorcontrib><creatorcontrib>Santos, Eva</creatorcontrib><creatorcontrib>Cequier, Enrique</creatorcontrib><creatorcontrib>Bo, Carles</creatorcontrib><creatorcontrib>de Mendoza, Javier</creatorcontrib><collection>Istex</collection><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>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huerta, Elisa</au><au>Serapian, Stefano Artin</au><au>Santos, Eva</au><au>Cequier, Enrique</au><au>Bo, Carles</au><au>de Mendoza, Javier</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molecular Basis for the Recognition of Higher Fullerenes into Ureidopyrimidinone-Cyclotriveratrylene Self-Assembled Capsules</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-09-12</date><risdate>2016</risdate><volume>22</volume><issue>38</issue><spage>13496</spage><epage>13505</epage><pages>13496-13505</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Fullerenes C60, C70, and C84 may be readily encaged within a hydrogen‐bonded dimeric capsule, based on two concave cyclotriveratrylene (CTV) scaffolds, each containing three self‐complementary 2‐ureido‐4‐[1H]‐pyrimidinone (UPy) subunits. NMR spectroscopy and circular dichroism studies, complemented by dispersion‐corrected DFT calculations, are reported with the aim of characterizing such capsule–fullerene complexes both structurally and energetically. Six fullerenes are considered: in agreement with experiments, calculations find that encapsulation is most favorable for C84 (on a par with C90), and follows the trend C60<C70<C76<C78<C84≈C90. As also found by NMR spectroscopy, the most stable capsules are formed by monomers of identical stereochemistry with UPy and the OMe groups of CTV in a mutual anti orientation and UPy–CTV ethylene linkers within the capsular surface plane. Up to C78, encapsulation is favored by increasing host–guest contacts, but the trend is thereafter increasingly inhibited by growing capsule strain.
Catch a fullerene! Supramolecular dimeric capsules (see figure), based on cyclotriveratrylene equipped with self‐complementary ureidopyrimidinone moieties, show selectivity towards C84 and C70 over C60. Combining theory and experiment, the molecular basis of such selectivity is explored.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27405088</pmid><doi>10.1002/chem.201601690</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-9581-2922</orcidid><orcidid>https://orcid.org/0000-0003-0122-8499</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Buckminsterfullerene Chemistry circular dichroism density functional calculations Encapsulation Ethylene Fullerenes host-guest systems Mathematical analysis NMR spectroscopy Selectivity Spectrum analysis Trends |
| title | Molecular Basis for the Recognition of Higher Fullerenes into Ureidopyrimidinone-Cyclotriveratrylene Self-Assembled Capsules |
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