Halogen- and Hydrogen-Bonding Catenanes for Halide-Anion Recognition
Halogen‐bonding (XB) interactions were exploited in the solution‐phase assembly of anion‐templated pseudorotaxanes between an isophthalamide‐containing macrocycle and bromo‐ or iodo‐functionalised pyridinium threading components. 1H NMR spectroscopic titration investigations demonstrated that such X...
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| Veröffentlicht in: | Chemistry : a European journal 2014-07, Vol.20 (27), p.8379-8385 |
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| creator | Gilday, Lydia C. Beer, Paul D. |
| description | Halogen‐bonding (XB) interactions were exploited in the solution‐phase assembly of anion‐templated pseudorotaxanes between an isophthalamide‐containing macrocycle and bromo‐ or iodo‐functionalised pyridinium threading components. 1H NMR spectroscopic titration investigations demonstrated that such XB interpenetrated assemblies are more stable than analogous hydrogen bonding (HB) pseudorotaxanes. The stability of the anion‐templated halogen‐bonded pseudorotaxane architectures was exploited in the preparation of new halogen‐bonding interlocked catenane species through a Grubbs’ ring‐closing metathesis (RCM) clipping methodology. The catenanes’ anion recognition properties in the competitive CDCl3/CD3OD 1:1 solvent mixture revealed selectivity for the heavier halides iodide and bromide over chloride and acetate.
Agent Bond: Halogen‐bonding interactions were exploited in the solution‐phase assembly and construction of anion‐templated pseudorotaxanes and catenanes. The catenanes' anion‐recognition properties in competitive protic‐solvent mixture revealed selectivity for the heavier halides and no evidence of binding the basic acetate anion (see figure). |
| doi_str_mv | 10.1002/chem.201402752 |
| format | Article |
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Agent Bond: Halogen‐bonding interactions were exploited in the solution‐phase assembly and construction of anion‐templated pseudorotaxanes and catenanes. The catenanes' anion‐recognition properties in competitive protic‐solvent mixture revealed selectivity for the heavier halides and no evidence of binding the basic acetate anion (see figure).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201402752</identifier><identifier>PMID: 24888346</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Acetates ; Anions ; Anions - chemistry ; Assembly ; Bonding agents ; catenanes ; Catenanes - chemical synthesis ; Catenanes - chemistry ; Chemistry ; Chlorides ; Halides ; halogen bonding ; Halogens - chemistry ; Hydrogen Bonding ; Magnetic Resonance Spectroscopy ; molecular recognition ; Recognition ; Rotaxanes - chemical synthesis ; Rotaxanes - chemistry ; Selectivity ; supramolecular chemistry</subject><ispartof>Chemistry : a European journal, 2014-07, Vol.20 (27), p.8379-8385</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5842-768cc191412b0ce94fb4ab32efc5ae75a2818841a5e1ffad2cbe8313295fce4d3</citedby><cites>FETCH-LOGICAL-c5842-768cc191412b0ce94fb4ab32efc5ae75a2818841a5e1ffad2cbe8313295fce4d3</cites></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.201402752$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201402752$$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/24888346$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gilday, Lydia C.</creatorcontrib><creatorcontrib>Beer, Paul D.</creatorcontrib><title>Halogen- and Hydrogen-Bonding Catenanes for Halide-Anion Recognition</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Halogen‐bonding (XB) interactions were exploited in the solution‐phase assembly of anion‐templated pseudorotaxanes between an isophthalamide‐containing macrocycle and bromo‐ or iodo‐functionalised pyridinium threading components. 1H NMR spectroscopic titration investigations demonstrated that such XB interpenetrated assemblies are more stable than analogous hydrogen bonding (HB) pseudorotaxanes. The stability of the anion‐templated halogen‐bonded pseudorotaxane architectures was exploited in the preparation of new halogen‐bonding interlocked catenane species through a Grubbs’ ring‐closing metathesis (RCM) clipping methodology. The catenanes’ anion recognition properties in the competitive CDCl3/CD3OD 1:1 solvent mixture revealed selectivity for the heavier halides iodide and bromide over chloride and acetate.
Agent Bond: Halogen‐bonding interactions were exploited in the solution‐phase assembly and construction of anion‐templated pseudorotaxanes and catenanes. The catenanes' anion‐recognition properties in competitive protic‐solvent mixture revealed selectivity for the heavier halides and no evidence of binding the basic acetate anion (see figure).</description><subject>Acetates</subject><subject>Anions</subject><subject>Anions - chemistry</subject><subject>Assembly</subject><subject>Bonding agents</subject><subject>catenanes</subject><subject>Catenanes - chemical synthesis</subject><subject>Catenanes - chemistry</subject><subject>Chemistry</subject><subject>Chlorides</subject><subject>Halides</subject><subject>halogen bonding</subject><subject>Halogens - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>molecular recognition</subject><subject>Recognition</subject><subject>Rotaxanes - chemical synthesis</subject><subject>Rotaxanes - chemistry</subject><subject>Selectivity</subject><subject>supramolecular chemistry</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1vEzEURS1ERUNhyxKNxIbNpH7-GNvLMrQNUilSacXS8njehCkTu9iJaP49LikRYtOVbencI793CXkDdA6UsmP_HVdzRkFQpiR7RmYgGdRcNfI5mVEjVN1Ibg7Jy5xvKaWm4fwFOWRCa81FMyMfF26KSwx15UJfLbZ9-vP6EEM_hmXVujUGFzBXQ0xVYcce65MwxlBdoY_LMK7L_RU5GNyU8fXjeURuzk6v20V98eX8U3tyUXupBatVo70HAwJYRz0aMXTCdZzh4KVDJR3ToLUAJxGGwfXMd6g5cGbk4FH0_Ii833nvUvy5wby2qzF7nKbyw7jJFpRSxigA_jQqBXBV3FDQd_-ht3GTQhmkUNwoo8vSCjXfUT7FnBMO9i6NK5e2Fqh9qMI-VGH3VZTA20ftplthv8f_7r4AZgf8GifcPqGz7eL087_yepcd8xrv91mXfthGcSXtt8tzK7_yq1ZJYy_5bwQSolM</recordid><startdate>20140701</startdate><enddate>20140701</enddate><creator>Gilday, Lydia C.</creator><creator>Beer, Paul D.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</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></search><sort><creationdate>20140701</creationdate><title>Halogen- and Hydrogen-Bonding Catenanes for Halide-Anion Recognition</title><author>Gilday, Lydia C. ; Beer, Paul D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5842-768cc191412b0ce94fb4ab32efc5ae75a2818841a5e1ffad2cbe8313295fce4d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Acetates</topic><topic>Anions</topic><topic>Anions - chemistry</topic><topic>Assembly</topic><topic>Bonding agents</topic><topic>catenanes</topic><topic>Catenanes - chemical synthesis</topic><topic>Catenanes - chemistry</topic><topic>Chemistry</topic><topic>Chlorides</topic><topic>Halides</topic><topic>halogen bonding</topic><topic>Halogens - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>molecular recognition</topic><topic>Recognition</topic><topic>Rotaxanes - chemical synthesis</topic><topic>Rotaxanes - chemistry</topic><topic>Selectivity</topic><topic>supramolecular chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gilday, Lydia C.</creatorcontrib><creatorcontrib>Beer, Paul D.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</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>Gilday, Lydia C.</au><au>Beer, Paul D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Halogen- and Hydrogen-Bonding Catenanes for Halide-Anion Recognition</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2014-07-01</date><risdate>2014</risdate><volume>20</volume><issue>27</issue><spage>8379</spage><epage>8385</epage><pages>8379-8385</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Halogen‐bonding (XB) interactions were exploited in the solution‐phase assembly of anion‐templated pseudorotaxanes between an isophthalamide‐containing macrocycle and bromo‐ or iodo‐functionalised pyridinium threading components. 1H NMR spectroscopic titration investigations demonstrated that such XB interpenetrated assemblies are more stable than analogous hydrogen bonding (HB) pseudorotaxanes. The stability of the anion‐templated halogen‐bonded pseudorotaxane architectures was exploited in the preparation of new halogen‐bonding interlocked catenane species through a Grubbs’ ring‐closing metathesis (RCM) clipping methodology. The catenanes’ anion recognition properties in the competitive CDCl3/CD3OD 1:1 solvent mixture revealed selectivity for the heavier halides iodide and bromide over chloride and acetate.
Agent Bond: Halogen‐bonding interactions were exploited in the solution‐phase assembly and construction of anion‐templated pseudorotaxanes and catenanes. The catenanes' anion‐recognition properties in competitive protic‐solvent mixture revealed selectivity for the heavier halides and no evidence of binding the basic acetate anion (see figure).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24888346</pmid><doi>10.1002/chem.201402752</doi><tpages>7</tpages></addata></record> |
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| source | MEDLINE; Wiley Online Library All Journals |
| subjects | Acetates Anions Anions - chemistry Assembly Bonding agents catenanes Catenanes - chemical synthesis Catenanes - chemistry Chemistry Chlorides Halides halogen bonding Halogens - chemistry Hydrogen Bonding Magnetic Resonance Spectroscopy molecular recognition Recognition Rotaxanes - chemical synthesis Rotaxanes - chemistry Selectivity supramolecular chemistry |
| title | Halogen- and Hydrogen-Bonding Catenanes for Halide-Anion Recognition |
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