Coumarin-Strapped Calix[4]pyrrole: A Fluorogenic Anion Receptor Modulated by Cation and Anion Binding
A new strapped calix[4]pyrrole containing a fluorophore as part of the strap has been synthesized and characterized. Association constants with various anions have been determined using both fluorescence titration and isothermal titrations calorimetry (ITC). The two sets of association constants wer...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-09, Vol.127 (36), p.12510-12512 |
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| container_end_page | 12512 |
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| container_issue | 36 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 127 |
| creator | Miyaji, Hidekazu Kim, Hae-Kyung Sim, Eun-Kyung Lee, Chang-Kiu Cho, Won-Seob Sessler, Jonathan L Lee, Chang-Hee |
| description | A new strapped calix[4]pyrrole containing a fluorophore as part of the strap has been synthesized and characterized. Association constants with various anions have been determined using both fluorescence titration and isothermal titrations calorimetry (ITC). The two sets of association constants were found to be in good agreement with one another. The fluorescence emission properties of this new receptor could be controlled by addition of Na+ (or H2O) and anions. However, the fluorescence quenching by anions is only observed in the presence of Na+ (or H2O). All the experimental evidence is consistent with the notion that independent PET processes are modulated by separate cation and anion recognition events. As such, this system operates as an elementary logic gate wherein anion and cation concentrations serve as the input and fluorescence intensity changes provide the output. |
| doi_str_mv | 10.1021/ja053612y |
| format | Article |
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Association constants with various anions have been determined using both fluorescence titration and isothermal titrations calorimetry (ITC). The two sets of association constants were found to be in good agreement with one another. The fluorescence emission properties of this new receptor could be controlled by addition of Na+ (or H2O) and anions. However, the fluorescence quenching by anions is only observed in the presence of Na+ (or H2O). All the experimental evidence is consistent with the notion that independent PET processes are modulated by separate cation and anion recognition events. As such, this system operates as an elementary logic gate wherein anion and cation concentrations serve as the input and fluorescence intensity changes provide the output.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja053612y</identifier><identifier>PMID: 16144397</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Anions - chemistry ; Calixarenes - chemical synthesis ; Calixarenes - chemistry ; Cations - chemistry ; Chemistry ; Coumarins - chemistry ; Exact sciences and technology ; General and physical chemistry ; Molecular Structure ; Porphyrins - chemical synthesis ; Porphyrins - chemistry ; Solution properties ; Solutions</subject><ispartof>Journal of the American Chemical Society, 2005-09, Vol.127 (36), p.12510-12512</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-6dc0cd4a66594f1c0dc61af2e74fbca6cbc167762636c32fe4d54d70377fbecc3</citedby><cites>FETCH-LOGICAL-a447t-6dc0cd4a66594f1c0dc61af2e74fbca6cbc167762636c32fe4d54d70377fbecc3</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/ja053612y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja053612y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17112971$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16144397$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miyaji, Hidekazu</creatorcontrib><creatorcontrib>Kim, Hae-Kyung</creatorcontrib><creatorcontrib>Sim, Eun-Kyung</creatorcontrib><creatorcontrib>Lee, Chang-Kiu</creatorcontrib><creatorcontrib>Cho, Won-Seob</creatorcontrib><creatorcontrib>Sessler, Jonathan L</creatorcontrib><creatorcontrib>Lee, Chang-Hee</creatorcontrib><title>Coumarin-Strapped Calix[4]pyrrole: A Fluorogenic Anion Receptor Modulated by Cation and Anion Binding</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A new strapped calix[4]pyrrole containing a fluorophore as part of the strap has been synthesized and characterized. Association constants with various anions have been determined using both fluorescence titration and isothermal titrations calorimetry (ITC). The two sets of association constants were found to be in good agreement with one another. The fluorescence emission properties of this new receptor could be controlled by addition of Na+ (or H2O) and anions. However, the fluorescence quenching by anions is only observed in the presence of Na+ (or H2O). All the experimental evidence is consistent with the notion that independent PET processes are modulated by separate cation and anion recognition events. As such, this system operates as an elementary logic gate wherein anion and cation concentrations serve as the input and fluorescence intensity changes provide the output.</description><subject>Anions - chemistry</subject><subject>Calixarenes - chemical synthesis</subject><subject>Calixarenes - chemistry</subject><subject>Cations - chemistry</subject><subject>Chemistry</subject><subject>Coumarins - chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Molecular Structure</subject><subject>Porphyrins - chemical synthesis</subject><subject>Porphyrins - chemistry</subject><subject>Solution properties</subject><subject>Solutions</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E9rFDEYBvAgit1WD34BmYuCh7H5N8mut-1ia2EXpa0UKhLeSTI162wyJjPQvXnt1_STNGWH7sVTeHl_70N4EHpD8EeCKTleA66YIHT7DE1IRXFZESqeownGmJZyKtgBOkxpnUdOp-QlOiCCcM5mcoJ-LcKwgeh8edlH6DprigW07u4H_9ltYwyt_fTv730xL07bIcRwa73Txdy74IsLq23Xh1isghla6PNpvc3X_eMSvBnZifPG-dtX6EUDbbKvx_cIfT_9fLX4Ui6_np0v5ssSOJd9KYzG2nAQoprxhmhstCDQUCt5U2sQutZESCmoYEIz2lhuKm4kZlI2tdWaHaH3u9wuhj-DTb3auKRt24K3YUhKTCtBGaUZfthBHUNK0Taqiy5XsVUEq8da1VOt2b4dQ4d6Y81ejj1m8G4EkDS0TQSvXdo7SQidSZJduXMu9fbuaQ_xtxKSyUpdfbtUNxfXN9crvlLLfS7opNZhiD53958PPgCUc5yF</recordid><startdate>20050914</startdate><enddate>20050914</enddate><creator>Miyaji, Hidekazu</creator><creator>Kim, Hae-Kyung</creator><creator>Sim, Eun-Kyung</creator><creator>Lee, Chang-Kiu</creator><creator>Cho, Won-Seob</creator><creator>Sessler, Jonathan L</creator><creator>Lee, Chang-Hee</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>20050914</creationdate><title>Coumarin-Strapped Calix[4]pyrrole: A Fluorogenic Anion Receptor Modulated by Cation and Anion Binding</title><author>Miyaji, Hidekazu ; Kim, Hae-Kyung ; Sim, Eun-Kyung ; Lee, Chang-Kiu ; Cho, Won-Seob ; Sessler, Jonathan L ; Lee, Chang-Hee</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-6dc0cd4a66594f1c0dc61af2e74fbca6cbc167762636c32fe4d54d70377fbecc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Anions - chemistry</topic><topic>Calixarenes - chemical synthesis</topic><topic>Calixarenes - chemistry</topic><topic>Cations - chemistry</topic><topic>Chemistry</topic><topic>Coumarins - chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Molecular Structure</topic><topic>Porphyrins - chemical synthesis</topic><topic>Porphyrins - chemistry</topic><topic>Solution properties</topic><topic>Solutions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miyaji, Hidekazu</creatorcontrib><creatorcontrib>Kim, Hae-Kyung</creatorcontrib><creatorcontrib>Sim, Eun-Kyung</creatorcontrib><creatorcontrib>Lee, Chang-Kiu</creatorcontrib><creatorcontrib>Cho, Won-Seob</creatorcontrib><creatorcontrib>Sessler, Jonathan L</creatorcontrib><creatorcontrib>Lee, Chang-Hee</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 the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miyaji, Hidekazu</au><au>Kim, Hae-Kyung</au><au>Sim, Eun-Kyung</au><au>Lee, Chang-Kiu</au><au>Cho, Won-Seob</au><au>Sessler, Jonathan L</au><au>Lee, Chang-Hee</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Coumarin-Strapped Calix[4]pyrrole: A Fluorogenic Anion Receptor Modulated by Cation and Anion Binding</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-09-14</date><risdate>2005</risdate><volume>127</volume><issue>36</issue><spage>12510</spage><epage>12512</epage><pages>12510-12512</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>A new strapped calix[4]pyrrole containing a fluorophore as part of the strap has been synthesized and characterized. Association constants with various anions have been determined using both fluorescence titration and isothermal titrations calorimetry (ITC). The two sets of association constants were found to be in good agreement with one another. The fluorescence emission properties of this new receptor could be controlled by addition of Na+ (or H2O) and anions. However, the fluorescence quenching by anions is only observed in the presence of Na+ (or H2O). All the experimental evidence is consistent with the notion that independent PET processes are modulated by separate cation and anion recognition events. As such, this system operates as an elementary logic gate wherein anion and cation concentrations serve as the input and fluorescence intensity changes provide the output.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16144397</pmid><doi>10.1021/ja053612y</doi><tpages>3</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Anions - chemistry Calixarenes - chemical synthesis Calixarenes - chemistry Cations - chemistry Chemistry Coumarins - chemistry Exact sciences and technology General and physical chemistry Molecular Structure Porphyrins - chemical synthesis Porphyrins - chemistry Solution properties Solutions |
| title | Coumarin-Strapped Calix[4]pyrrole: A Fluorogenic Anion Receptor Modulated by Cation and Anion Binding |
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