Quantitative Active Transport in [2]Rotaxane Using a One-Shot Acylation Reaction toward the Linear Molecular Motor
A rotaxane consisting of a crown ether wheel and a secondary ammonium salt axle, on which a neopentyl-type end-cap was placed close to the ammonium moiety, was prepared. When the rotaxane was treated by excess triethylamine, the wheel component thermodynamically moved over the proximate neopentyl gr...
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| Veröffentlicht in: | Journal of organic chemistry 2008-12, Vol.73 (23), p.9245-9250 |
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| container_end_page | 9250 |
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| container_issue | 23 |
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| container_title | Journal of organic chemistry |
| container_volume | 73 |
| creator | Makita, Yoshimasa Kihara, Nobuhiro Takata, Toshikazu |
| description | A rotaxane consisting of a crown ether wheel and a secondary ammonium salt axle, on which a neopentyl-type end-cap was placed close to the ammonium moiety, was prepared. When the rotaxane was treated by excess triethylamine, the wheel component thermodynamically moved over the proximate neopentyl group to deconstruct the interlocked structure. The wheel component in the rotaxane, however, quantitatively moved against the proximate end-cap by the action of trifluoroacetic anhydride in the presence of excess triethylamine. This motion, which was driven by the simple one-shot acylation reaction, can be referred as the active transport. When the distant end-cap is of the neopentyl-type, the axle can be thermally dethreaded from the distant end-cap after the acylative transport. The series of the wheel movement controlled by the neopentyl group can be the basic motion of the unidirectional linear molecular motor. |
| doi_str_mv | 10.1021/jo8013726 |
| format | Article |
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When the rotaxane was treated by excess triethylamine, the wheel component thermodynamically moved over the proximate neopentyl group to deconstruct the interlocked structure. The wheel component in the rotaxane, however, quantitatively moved against the proximate end-cap by the action of trifluoroacetic anhydride in the presence of excess triethylamine. This motion, which was driven by the simple one-shot acylation reaction, can be referred as the active transport. When the distant end-cap is of the neopentyl-type, the axle can be thermally dethreaded from the distant end-cap after the acylative transport. The series of the wheel movement controlled by the neopentyl group can be the basic motion of the unidirectional linear molecular motor.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo8013726</identifier><identifier>PMID: 18954114</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acylation ; Adenosine Triphosphate - chemistry ; Chemistry ; Chemistry, Organic - methods ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Kinetics ; Models, Chemical ; Molecular Structure ; Organic chemistry ; Phosphorylation ; Polymers - chemistry ; Preparations and properties ; Rotaxanes - chemistry ; Thermodynamics</subject><ispartof>Journal of organic chemistry, 2008-12, Vol.73 (23), p.9245-9250</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a448t-38e5003a0e054a9df393c69dbe17f366bf5db4675ed0a927493337126142a47c3</citedby><cites>FETCH-LOGICAL-a448t-38e5003a0e054a9df393c69dbe17f366bf5db4675ed0a927493337126142a47c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo8013726$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo8013726$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20955314$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18954114$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Makita, Yoshimasa</creatorcontrib><creatorcontrib>Kihara, Nobuhiro</creatorcontrib><creatorcontrib>Takata, Toshikazu</creatorcontrib><title>Quantitative Active Transport in [2]Rotaxane Using a One-Shot Acylation Reaction toward the Linear Molecular Motor</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A rotaxane consisting of a crown ether wheel and a secondary ammonium salt axle, on which a neopentyl-type end-cap was placed close to the ammonium moiety, was prepared. When the rotaxane was treated by excess triethylamine, the wheel component thermodynamically moved over the proximate neopentyl group to deconstruct the interlocked structure. The wheel component in the rotaxane, however, quantitatively moved against the proximate end-cap by the action of trifluoroacetic anhydride in the presence of excess triethylamine. This motion, which was driven by the simple one-shot acylation reaction, can be referred as the active transport. When the distant end-cap is of the neopentyl-type, the axle can be thermally dethreaded from the distant end-cap after the acylative transport. The series of the wheel movement controlled by the neopentyl group can be the basic motion of the unidirectional linear molecular motor.</description><subject>Acylation</subject><subject>Adenosine Triphosphate - chemistry</subject><subject>Chemistry</subject><subject>Chemistry, Organic - methods</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Kinetics</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Phosphorylation</subject><subject>Polymers - chemistry</subject><subject>Preparations and properties</subject><subject>Rotaxanes - chemistry</subject><subject>Thermodynamics</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1vEzEQhi0EoqFw4A8gXxDisOBv7x6rqAWkQKFNLyBkTbxe6rKxg-2F9t9jkihwwJcZyc-8mnkQekrJK0oYfX0TW0K5ZuoemlHJSKM6Iu6jGSGMNZwpfoQe5XxD6pNSPkRHtO2koFTMUPo0QSi-QPE_HT6x27JMEPImpoJ9wF_Y14tY4BaCw1fZh28Y8HlwzeV1LHXgbqyjMeALB3bblPgLUo_LtcMLHxwk_D6Ozk7jtisxPUYPBhize7Kvx-jq7HQ5f9sszt-8m58sGhCiLQ1vnSSEA3FECuj6gXfcqq5fOaoHrtRqkP1KKC1dT6BjWnScc02ZooKB0JYfoxe73E2KPyaXi1n7bN041kvilI2uPKeqJZV8uSNtijknN5hN8mtId4YS88ewORiu7LN96rRau_4vuVdaged7ALKFcagurc8HjpFOSr7lmh3nc3G3h39I343SXEuz_Hhp5q08-yzIB_NPLthc95lSqPL-s-Bv70ydDg</recordid><startdate>20081205</startdate><enddate>20081205</enddate><creator>Makita, Yoshimasa</creator><creator>Kihara, Nobuhiro</creator><creator>Takata, Toshikazu</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</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>7X8</scope></search><sort><creationdate>20081205</creationdate><title>Quantitative Active Transport in [2]Rotaxane Using a One-Shot Acylation Reaction toward the Linear Molecular Motor</title><author>Makita, Yoshimasa ; Kihara, Nobuhiro ; Takata, Toshikazu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a448t-38e5003a0e054a9df393c69dbe17f366bf5db4675ed0a927493337126142a47c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Acylation</topic><topic>Adenosine Triphosphate - chemistry</topic><topic>Chemistry</topic><topic>Chemistry, Organic - methods</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Kinetics</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Phosphorylation</topic><topic>Polymers - chemistry</topic><topic>Preparations and properties</topic><topic>Rotaxanes - chemistry</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Makita, Yoshimasa</creatorcontrib><creatorcontrib>Kihara, Nobuhiro</creatorcontrib><creatorcontrib>Takata, Toshikazu</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Makita, Yoshimasa</au><au>Kihara, Nobuhiro</au><au>Takata, Toshikazu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Quantitative Active Transport in [2]Rotaxane Using a One-Shot Acylation Reaction toward the Linear Molecular Motor</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-12-05</date><risdate>2008</risdate><volume>73</volume><issue>23</issue><spage>9245</spage><epage>9250</epage><pages>9245-9250</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A rotaxane consisting of a crown ether wheel and a secondary ammonium salt axle, on which a neopentyl-type end-cap was placed close to the ammonium moiety, was prepared. When the rotaxane was treated by excess triethylamine, the wheel component thermodynamically moved over the proximate neopentyl group to deconstruct the interlocked structure. The wheel component in the rotaxane, however, quantitatively moved against the proximate end-cap by the action of trifluoroacetic anhydride in the presence of excess triethylamine. This motion, which was driven by the simple one-shot acylation reaction, can be referred as the active transport. When the distant end-cap is of the neopentyl-type, the axle can be thermally dethreaded from the distant end-cap after the acylative transport. The series of the wheel movement controlled by the neopentyl group can be the basic motion of the unidirectional linear molecular motor.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18954114</pmid><doi>10.1021/jo8013726</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2008-12, Vol.73 (23), p.9245-9250 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Acylation Adenosine Triphosphate - chemistry Chemistry Chemistry, Organic - methods Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Kinetics Models, Chemical Molecular Structure Organic chemistry Phosphorylation Polymers - chemistry Preparations and properties Rotaxanes - chemistry Thermodynamics |
| title | Quantitative Active Transport in [2]Rotaxane Using a One-Shot Acylation Reaction toward the Linear Molecular Motor |
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