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An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement
The assembly of a discrete hydrogen‐bonded molecular tube from eight small identical monomers is reported. Tube assembly was accomplished by means of selective heterodimerization between isocytosine and ureidopyrimidinone hydrogen‐bonding motifs embedded in an enantiopure bicyclic building block, le...
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| Published in: | Angewandte Chemie 2016-01, Vol.128 (1), p.216-220 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | eng ; ger |
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| cited_by | cdi_FETCH-LOGICAL-c2612-b05c73dfe202e61ad14251b23b3eb2c45639b5c2fd8791ce9b525517e8b923b3 |
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| cites | cdi_FETCH-LOGICAL-c2612-b05c73dfe202e61ad14251b23b3eb2c45639b5c2fd8791ce9b525517e8b923b3 |
| container_end_page | 220 |
| container_issue | 1 |
| container_start_page | 216 |
| container_title | Angewandte Chemie |
| container_volume | 128 |
| creator | Račkauskaitė, Dovilė Gegevičius, Rokas Matsuo, Yutaka Wärnmark, Kenneth Orentas, Edvinas |
| description | The assembly of a discrete hydrogen‐bonded molecular tube from eight small identical monomers is reported. Tube assembly was accomplished by means of selective heterodimerization between isocytosine and ureidopyrimidinone hydrogen‐bonding motifs embedded in an enantiopure bicyclic building block, leading to the selective formation of an octameric supramolecular tube. Upon introduction of a fullerene guest molecule, the octameric tube rearranges into a tetrameric inclusion complex and the hydrogen‐bonding mode is switched. The dynamic behavior of the system is further explored in solvent‐ and guest‐responsive self‐sorting experiments.
Sei mein Gast: Eine oktamere supramolekulare Röhre wurde mithilfe einer selektiven Heterodimerisierung zwischen den Wasserstoffbrücken‐Partnern Isocytosin und Ureidopyrimidinon aus identischen kleinen bicyclischen Bausteinen aufgebaut. Durch Behandlung mit C60 wird der Wasserstoffbrücken‐Modus so geändert, dass sich die Röhre in einen tetrameren Einschlusskomplex umlagert. |
| doi_str_mv | 10.1002/ange.201508362 |
| format | article |
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Sei mein Gast: Eine oktamere supramolekulare Röhre wurde mithilfe einer selektiven Heterodimerisierung zwischen den Wasserstoffbrücken‐Partnern Isocytosin und Ureidopyrimidinon aus identischen kleinen bicyclischen Bausteinen aufgebaut. Durch Behandlung mit C60 wird der Wasserstoffbrücken‐Modus so geändert, dass sich die Röhre in einen tetrameren Einschlusskomplex umlagert.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201508362</identifier><language>eng ; ger</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Assembly ; Chemical bonds ; Chemistry ; Dynamical systems ; Dynamics ; Einschlussverbindungen ; Formations ; Fullerene ; Fullerenes ; Hydrogen ; Hydrogen bonding ; Inclusion complexes ; Monomers ; Selbstsortierung ; Supramolekulare Chemie ; Tubes ; Wasserstoffbrücken</subject><ispartof>Angewandte Chemie, 2016-01, Vol.128 (1), p.216-220</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2612-b05c73dfe202e61ad14251b23b3eb2c45639b5c2fd8791ce9b525517e8b923b3</citedby><cites>FETCH-LOGICAL-c2612-b05c73dfe202e61ad14251b23b3eb2c45639b5c2fd8791ce9b525517e8b923b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids></links><search><creatorcontrib>Račkauskaitė, Dovilė</creatorcontrib><creatorcontrib>Gegevičius, Rokas</creatorcontrib><creatorcontrib>Matsuo, Yutaka</creatorcontrib><creatorcontrib>Wärnmark, Kenneth</creatorcontrib><creatorcontrib>Orentas, Edvinas</creatorcontrib><title>An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>The assembly of a discrete hydrogen‐bonded molecular tube from eight small identical monomers is reported. Tube assembly was accomplished by means of selective heterodimerization between isocytosine and ureidopyrimidinone hydrogen‐bonding motifs embedded in an enantiopure bicyclic building block, leading to the selective formation of an octameric supramolecular tube. Upon introduction of a fullerene guest molecule, the octameric tube rearranges into a tetrameric inclusion complex and the hydrogen‐bonding mode is switched. The dynamic behavior of the system is further explored in solvent‐ and guest‐responsive self‐sorting experiments.
Sei mein Gast: Eine oktamere supramolekulare Röhre wurde mithilfe einer selektiven Heterodimerisierung zwischen den Wasserstoffbrücken‐Partnern Isocytosin und Ureidopyrimidinon aus identischen kleinen bicyclischen Bausteinen aufgebaut. Durch Behandlung mit C60 wird der Wasserstoffbrücken‐Modus so geändert, dass sich die Röhre in einen tetrameren Einschlusskomplex umlagert.</description><subject>Assembly</subject><subject>Chemical bonds</subject><subject>Chemistry</subject><subject>Dynamical systems</subject><subject>Dynamics</subject><subject>Einschlussverbindungen</subject><subject>Formations</subject><subject>Fullerene</subject><subject>Fullerenes</subject><subject>Hydrogen</subject><subject>Hydrogen bonding</subject><subject>Inclusion complexes</subject><subject>Monomers</subject><subject>Selbstsortierung</subject><subject>Supramolekulare Chemie</subject><subject>Tubes</subject><subject>Wasserstoffbrücken</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkU1r3DAQhkVJoZu0154NvfSi7UiyZLm3TdhsEvIByUIPPQhZHi9OvfJGsmn331dmQwg5tKdB8DzinXkJ-cxgzgD4N-s3OOfAJGih-DsyY5IzKgpZHJEZQJ5TzfPyAzmO8REAFC_KGfm58NnSWz-0_W4MmF3s69Bv0NPT3tdYZ3dusFsMrcvWY4XfswfsGvrQh6H1m8z6OluNGAd66evRJfwebQhTkC364SN539gu4qfneULW58v12QW9vltdni2uqeOKcVqBdIWoG-TAUTFbs5xLVnFRCay4y6USZSUdb2pdlMxhenApWYG6KifohHw9fLsL_dOUxmzb6LDrrMd-jIbptLwWTEFCv7xBH_sx-BTOsJJrwTVo-U8qXRNULjVL1PxAudDHGLAxu9BubdgbBmYqxEx3MC-FJKE8CL_bDvf_oc3idrV87dKD28YB_7y4NvwyqkgVmx-3K6Pvz9UNXN2YXPwFihicIw</recordid><startdate>20160104</startdate><enddate>20160104</enddate><creator>Račkauskaitė, Dovilė</creator><creator>Gegevičius, Rokas</creator><creator>Matsuo, Yutaka</creator><creator>Wärnmark, Kenneth</creator><creator>Orentas, Edvinas</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20160104</creationdate><title>An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement</title><author>Račkauskaitė, Dovilė ; Gegevičius, Rokas ; Matsuo, Yutaka ; Wärnmark, Kenneth ; Orentas, Edvinas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2612-b05c73dfe202e61ad14251b23b3eb2c45639b5c2fd8791ce9b525517e8b923b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; ger</language><creationdate>2016</creationdate><topic>Assembly</topic><topic>Chemical bonds</topic><topic>Chemistry</topic><topic>Dynamical systems</topic><topic>Dynamics</topic><topic>Einschlussverbindungen</topic><topic>Formations</topic><topic>Fullerene</topic><topic>Fullerenes</topic><topic>Hydrogen</topic><topic>Hydrogen bonding</topic><topic>Inclusion complexes</topic><topic>Monomers</topic><topic>Selbstsortierung</topic><topic>Supramolekulare Chemie</topic><topic>Tubes</topic><topic>Wasserstoffbrücken</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Račkauskaitė, Dovilė</creatorcontrib><creatorcontrib>Gegevičius, Rokas</creatorcontrib><creatorcontrib>Matsuo, Yutaka</creatorcontrib><creatorcontrib>Wärnmark, Kenneth</creatorcontrib><creatorcontrib>Orentas, Edvinas</creatorcontrib><collection>Istex</collection><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><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Račkauskaitė, Dovilė</au><au>Gegevičius, Rokas</au><au>Matsuo, Yutaka</au><au>Wärnmark, Kenneth</au><au>Orentas, Edvinas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2016-01-04</date><risdate>2016</risdate><volume>128</volume><issue>1</issue><spage>216</spage><epage>220</epage><pages>216-220</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The assembly of a discrete hydrogen‐bonded molecular tube from eight small identical monomers is reported. Tube assembly was accomplished by means of selective heterodimerization between isocytosine and ureidopyrimidinone hydrogen‐bonding motifs embedded in an enantiopure bicyclic building block, leading to the selective formation of an octameric supramolecular tube. Upon introduction of a fullerene guest molecule, the octameric tube rearranges into a tetrameric inclusion complex and the hydrogen‐bonding mode is switched. The dynamic behavior of the system is further explored in solvent‐ and guest‐responsive self‐sorting experiments.
Sei mein Gast: Eine oktamere supramolekulare Röhre wurde mithilfe einer selektiven Heterodimerisierung zwischen den Wasserstoffbrücken‐Partnern Isocytosin und Ureidopyrimidinon aus identischen kleinen bicyclischen Bausteinen aufgebaut. Durch Behandlung mit C60 wird der Wasserstoffbrücken‐Modus so geändert, dass sich die Röhre in einen tetrameren Einschlusskomplex umlagert.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201508362</doi><tpages>5</tpages></addata></record> |
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| identifier | ISSN: 0044-8249 |
| ispartof | Angewandte Chemie, 2016-01, Vol.128 (1), p.216-220 |
| issn | 0044-8249 1521-3757 |
| language | eng ; ger |
| recordid | cdi_proquest_miscellaneous_1800483160 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Assembly Chemical bonds Chemistry Dynamical systems Dynamics Einschlussverbindungen Formations Fullerene Fullerenes Hydrogen Hydrogen bonding Inclusion complexes Monomers Selbstsortierung Supramolekulare Chemie Tubes Wasserstoffbrücken |
| title | An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement |
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