A Copper(II) Ion-Selective On−Off-Type Fluoroionophore Based on Zinc Porphyrin−Dipyridylamino
A new copper(II) fluorescent sensor 5,10,15,20-tetra((p-N,N-bis(2-pyridyl)amino)phenyl)porphyrin zinc (1) has been designed and synthesized by the Ullmann-type condensation of bromoporphyrin zinc with 2,2‘-dipyridylamine (dpa) under copper powder as a catalyst as well as with K2CO3 as the base in a...
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| Veröffentlicht in: | Inorganic chemistry 2007-09, Vol.46 (19), p.7749-7755 |
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| creator | Weng, Yan-Qin Yue, Fan Zhong, Yong-Rui Ye, Bao-Hui |
| description | A new copper(II) fluorescent sensor 5,10,15,20-tetra((p-N,N-bis(2-pyridyl)amino)phenyl)porphyrin zinc (1) has been designed and synthesized by the Ullmann-type condensation of bromoporphyrin zinc with 2,2‘-dipyridylamine (dpa) under copper powder as a catalyst as well as with K2CO3 as the base in a DMF solution. It consists of two separately functional moieties: the zinc porphyrin performs as a fluorophore, and the dpa-linked-to-zinc porphyrin acts as a selected binding site for metal ions. It displays a high selectivity and antidisturbance for the Cu2+ ion among the metal ions examined (Na+, Mg2+, Cr3+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, and Fe3+) and exhibits fluorescence quenching upon the binding of the Cu2+ ion with an “on−off”-type fluoroionophoric switching property. The detection limit is found to be 3.3 × 10-7 M (3s blank) for Cu2+ ion in methanol solution, and its fluorescence can be revived by the addition of EDTA disodium solution. The design strategy and remarkable photophysical properties of sensor 1 help to extend the development of fluorescent sensors for metal ions. |
| doi_str_mv | 10.1021/ic061709v |
| format | Article |
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It consists of two separately functional moieties: the zinc porphyrin performs as a fluorophore, and the dpa-linked-to-zinc porphyrin acts as a selected binding site for metal ions. It displays a high selectivity and antidisturbance for the Cu2+ ion among the metal ions examined (Na+, Mg2+, Cr3+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, and Fe3+) and exhibits fluorescence quenching upon the binding of the Cu2+ ion with an “on−off”-type fluoroionophoric switching property. The detection limit is found to be 3.3 × 10-7 M (3s blank) for Cu2+ ion in methanol solution, and its fluorescence can be revived by the addition of EDTA disodium solution. The design strategy and remarkable photophysical properties of sensor 1 help to extend the development of fluorescent sensors for metal ions.</description><identifier>ISSN: 0020-1669</identifier><identifier>EISSN: 1520-510X</identifier><identifier>DOI: 10.1021/ic061709v</identifier><identifier>PMID: 17705364</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Copper - chemistry ; Fluorescent Dyes - chemistry ; Ions - chemistry ; Ligands ; Metalloporphyrins - chemical synthesis ; Metalloporphyrins - chemistry ; Molecular Structure ; Spectrometry, Fluorescence</subject><ispartof>Inorganic chemistry, 2007-09, Vol.46 (19), p.7749-7755</ispartof><rights>Copyright © 2007 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a417t-27ed9c1519ba1af0901cd7141807362e3be7f7bcf1ae1595ddb0c34b4513a5243</citedby><cites>FETCH-LOGICAL-a417t-27ed9c1519ba1af0901cd7141807362e3be7f7bcf1ae1595ddb0c34b4513a5243</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/ic061709v$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ic061709v$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17705364$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Weng, Yan-Qin</creatorcontrib><creatorcontrib>Yue, Fan</creatorcontrib><creatorcontrib>Zhong, Yong-Rui</creatorcontrib><creatorcontrib>Ye, Bao-Hui</creatorcontrib><title>A Copper(II) Ion-Selective On−Off-Type Fluoroionophore Based on Zinc Porphyrin−Dipyridylamino</title><title>Inorganic chemistry</title><addtitle>Inorg. Chem</addtitle><description>A new copper(II) fluorescent sensor 5,10,15,20-tetra((p-N,N-bis(2-pyridyl)amino)phenyl)porphyrin zinc (1) has been designed and synthesized by the Ullmann-type condensation of bromoporphyrin zinc with 2,2‘-dipyridylamine (dpa) under copper powder as a catalyst as well as with K2CO3 as the base in a DMF solution. It consists of two separately functional moieties: the zinc porphyrin performs as a fluorophore, and the dpa-linked-to-zinc porphyrin acts as a selected binding site for metal ions. It displays a high selectivity and antidisturbance for the Cu2+ ion among the metal ions examined (Na+, Mg2+, Cr3+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, and Fe3+) and exhibits fluorescence quenching upon the binding of the Cu2+ ion with an “on−off”-type fluoroionophoric switching property. The detection limit is found to be 3.3 × 10-7 M (3s blank) for Cu2+ ion in methanol solution, and its fluorescence can be revived by the addition of EDTA disodium solution. The design strategy and remarkable photophysical properties of sensor 1 help to extend the development of fluorescent sensors for metal ions.</description><subject>Copper - chemistry</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Ions - chemistry</subject><subject>Ligands</subject><subject>Metalloporphyrins - chemical synthesis</subject><subject>Metalloporphyrins - chemistry</subject><subject>Molecular Structure</subject><subject>Spectrometry, Fluorescence</subject><issn>0020-1669</issn><issn>1520-510X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFO20AQhldVq5KmPfACyBdQOZjO2F5vfEwCtEGpgpQgql5W6_VYLDhesxtH5A165hF5EowShUtP80vzzT_Sx9ghwhlChD-MhhQFZOsPrIc8gpAj_PnIegBdxjTNDtgX7-8BIIuT9DM7QCGAx2nSY2oYjG3TkPs-mZwGE1uHc6pIr8yagln98u95VpbhYtNQcFm11llja9vcWUfBSHkqAlsHf02tg2vrmruNM28n56bpUrGp1NLU9iv7VKrK07fd7LOby4vF-Fc4nf2cjIfTUCUoVmEkqMg0csxyhaqEDFAXAhMcgIjTiOKcRClyXaIi5Bkvihx0nOQJx1jxKIn77GTb2zj72JJfyaXxmqpK1WRbL9NBxJMBig483YLaWe8dlbJxZqncRiLIN59y77Njj3albb6k4p3cCeyAcAsYv6Kn_V65B5mKWHC5uJ7LqxH8nt-OR3La8cdbXmkv723r6s7Jfx6_AsiBjTE</recordid><startdate>20070917</startdate><enddate>20070917</enddate><creator>Weng, Yan-Qin</creator><creator>Yue, Fan</creator><creator>Zhong, Yong-Rui</creator><creator>Ye, Bao-Hui</creator><general>American Chemical Society</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>7X8</scope></search><sort><creationdate>20070917</creationdate><title>A Copper(II) Ion-Selective On−Off-Type Fluoroionophore Based on Zinc Porphyrin−Dipyridylamino</title><author>Weng, Yan-Qin ; Yue, Fan ; Zhong, Yong-Rui ; Ye, Bao-Hui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a417t-27ed9c1519ba1af0901cd7141807362e3be7f7bcf1ae1595ddb0c34b4513a5243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Copper - chemistry</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Ions - chemistry</topic><topic>Ligands</topic><topic>Metalloporphyrins - chemical synthesis</topic><topic>Metalloporphyrins - chemistry</topic><topic>Molecular Structure</topic><topic>Spectrometry, Fluorescence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Weng, Yan-Qin</creatorcontrib><creatorcontrib>Yue, Fan</creatorcontrib><creatorcontrib>Zhong, Yong-Rui</creatorcontrib><creatorcontrib>Ye, Bao-Hui</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>MEDLINE - Academic</collection><jtitle>Inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Weng, Yan-Qin</au><au>Yue, Fan</au><au>Zhong, Yong-Rui</au><au>Ye, Bao-Hui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Copper(II) Ion-Selective On−Off-Type Fluoroionophore Based on Zinc Porphyrin−Dipyridylamino</atitle><jtitle>Inorganic chemistry</jtitle><addtitle>Inorg. Chem</addtitle><date>2007-09-17</date><risdate>2007</risdate><volume>46</volume><issue>19</issue><spage>7749</spage><epage>7755</epage><pages>7749-7755</pages><issn>0020-1669</issn><eissn>1520-510X</eissn><abstract>A new copper(II) fluorescent sensor 5,10,15,20-tetra((p-N,N-bis(2-pyridyl)amino)phenyl)porphyrin zinc (1) has been designed and synthesized by the Ullmann-type condensation of bromoporphyrin zinc with 2,2‘-dipyridylamine (dpa) under copper powder as a catalyst as well as with K2CO3 as the base in a DMF solution. It consists of two separately functional moieties: the zinc porphyrin performs as a fluorophore, and the dpa-linked-to-zinc porphyrin acts as a selected binding site for metal ions. It displays a high selectivity and antidisturbance for the Cu2+ ion among the metal ions examined (Na+, Mg2+, Cr3+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, and Fe3+) and exhibits fluorescence quenching upon the binding of the Cu2+ ion with an “on−off”-type fluoroionophoric switching property. The detection limit is found to be 3.3 × 10-7 M (3s blank) for Cu2+ ion in methanol solution, and its fluorescence can be revived by the addition of EDTA disodium solution. The design strategy and remarkable photophysical properties of sensor 1 help to extend the development of fluorescent sensors for metal ions.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>17705364</pmid><doi>10.1021/ic061709v</doi><tpages>7</tpages></addata></record> |
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| subjects | Copper - chemistry Fluorescent Dyes - chemistry Ions - chemistry Ligands Metalloporphyrins - chemical synthesis Metalloporphyrins - chemistry Molecular Structure Spectrometry, Fluorescence |
| title | A Copper(II) Ion-Selective On−Off-Type Fluoroionophore Based on Zinc Porphyrin−Dipyridylamino |
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