An Ionically Driven Molecular IMPLICATION Gate Operating in Fluorescence Mode
An asymmetrically core‐extended boron–dipyrromethene (BDP) dye was equipped with two electron‐donating macrocyclic binding units with different metal ion preferences to operate as an ionically driven molecular IMPLICATION gate. A Na+‐responsive tetraoxa‐aza crown ether (R2) was integrated into the e...
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| Veröffentlicht in: | Chemistry : a European journal 2007-01, Vol.13 (32), p.8998-9003 |
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| creator | Rurack, Knut Trieflinger, Christian Koval'chuck, Anton Daub, Jörg |
| description | An asymmetrically core‐extended boron–dipyrromethene (BDP) dye was equipped with two electron‐donating macrocyclic binding units with different metal ion preferences to operate as an ionically driven molecular IMPLICATION gate. A Na+‐responsive tetraoxa‐aza crown ether (R2) was integrated into the extended π system of the BDP chromophore to trigger strong intramolecular charge transfer (ICT2) fluorescence and guarantee cation‐induced spectral shifts in absorption. A dithia‐oxa‐aza crown (R1) that responds to Ag+ was attached to the meso position of BDP in an electronically decoupled fashion to independently control a second ICT1 process of a quenching nature. The bifunctional molecule is designed in such a way that in the absence of both inputs, ICT1 does not compete with ICT2 and a high fluorescence output is obtained (InA=InB=0→Out=1). Accordingly, binding of only Ag+ at R1 (InA=1, InB=0) as well as complexation of both receptors (InA=InB=1) also yields Out=1. Only for the case in which Na+ is bound at R2 and R1 is in its free state does quenching occur, which is the distinguishing characteristic for the InA=0 and InB=1→Out=0 state that is required for a logic IMPLICATION gate and Boolean operations such as IF‐THEN or NOT.
Ein am Kern unsymmetrisch verlängerter Bordipyrromethen‐(BDP) Farbstoff wurde mit zwei Elektronen schiebenden makrozyklischen Bindungseinheiten, die sich in ihren Metallionenpräferenzen unterscheiden, versehen, um als molekulares IMPLICATION‐Gatter zu fungieren. Um eine starke intramolekulare Ladungstransfer‐ (intramolecular charge transfer, ICT2) Fluoreszenz zu generieren und Kationen induzierte spektrale Verschiebungen in Absorption zu garantieren, wurde ein auf Na+ ansprechender Tetraoxa‐aza‐Kronenether R2 in das verlängerte π‐System des BDP‐Chromophors integriert. Ein Dithia‐oxa‐aza‐Kronenether R1, welcher auf Ag+ anspricht, wurde an der meso‐Position des BDP‐Körpers in einer elektronisch entkoppelten Art und Weise eingeführt, um unabhängig von ICT2 einen zweiten, die Fluoreszenz löschenden ICT1 kontrollieren zu können. Das bifunktionelle Molekül wurde so konstruiert, dass ICT1 in der Abwesenheit beider Eingabeparameter nicht mit ICT2 konkurrieren kann und ein intensives Fluoreszenzsignal ausgegeben wird (InA= InB=0→Out=1). Dementsprechend führt die alleinige Bindung von Ag+ an R1 (InA=1, InB=0) sowie die Komplexierung beider Rezeptoren (InA=InB=1) ebenfalls zu Out=1. Nur wenn Na+ an R2 gebunden wird und R1 in freiem Zustand vorlie |
| doi_str_mv | 10.1002/chem.200700858 |
| format | Article |
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Ein am Kern unsymmetrisch verlängerter Bordipyrromethen‐(BDP) Farbstoff wurde mit zwei Elektronen schiebenden makrozyklischen Bindungseinheiten, die sich in ihren Metallionenpräferenzen unterscheiden, versehen, um als molekulares IMPLICATION‐Gatter zu fungieren. Um eine starke intramolekulare Ladungstransfer‐ (intramolecular charge transfer, ICT2) Fluoreszenz zu generieren und Kationen induzierte spektrale Verschiebungen in Absorption zu garantieren, wurde ein auf Na+ ansprechender Tetraoxa‐aza‐Kronenether R2 in das verlängerte π‐System des BDP‐Chromophors integriert. Ein Dithia‐oxa‐aza‐Kronenether R1, welcher auf Ag+ anspricht, wurde an der meso‐Position des BDP‐Körpers in einer elektronisch entkoppelten Art und Weise eingeführt, um unabhängig von ICT2 einen zweiten, die Fluoreszenz löschenden ICT1 kontrollieren zu können. Das bifunktionelle Molekül wurde so konstruiert, dass ICT1 in der Abwesenheit beider Eingabeparameter nicht mit ICT2 konkurrieren kann und ein intensives Fluoreszenzsignal ausgegeben wird (InA= InB=0→Out=1). Dementsprechend führt die alleinige Bindung von Ag+ an R1 (InA=1, InB=0) sowie die Komplexierung beider Rezeptoren (InA=InB=1) ebenfalls zu Out=1. Nur wenn Na+ an R2 gebunden wird und R1 in freiem Zustand vorliegt, erfolgt Fluoreszenzlöschung. Letzteres zeichnet den charakteristischen Zustand InA=0, InB=1→Out=0 aus, der für das logische IMPLICATION‐Gatter und Boolesche Operationen wie IF‐THEN oder NOT benötigt wird.
Fluorescent gates: A molecular IMPLICATION gate has been developed through the combination of two electronically decoupled charge‐transfer (CT) processes in an asymmetrically core‐extended boron–dipyrromethene (BDP) dye when both donors D1,2 carry different cation receptors. D1 is only an active quencher when D2 is bound (input 0/1) and a high fluorescence output at >700 nm is obtained for all other input cases (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.200700858</identifier><identifier>PMID: 17705328</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Boron Compounds - chemical synthesis ; Boron Compounds - chemistry ; charge transfer ; dyes/pigments ; Fluorescence ; Fluorescent Dyes - chemistry ; Ions - chemistry ; logic gates ; molecular devices ; Molecular Structure ; Porphobilinogen - analogs & derivatives ; Porphobilinogen - chemistry ; Quantum Theory</subject><ispartof>Chemistry : a European journal, 2007-01, Vol.13 (32), p.8998-9003</ispartof><rights>Copyright © 2007 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4878-414942555fe9c4437fbd00c2a86bd558ebd956981cf8983407c643c7e5e466e3</citedby><cites>FETCH-LOGICAL-c4878-414942555fe9c4437fbd00c2a86bd558ebd956981cf8983407c643c7e5e466e3</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.200700858$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.200700858$$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/17705328$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rurack, Knut</creatorcontrib><creatorcontrib>Trieflinger, Christian</creatorcontrib><creatorcontrib>Koval'chuck, Anton</creatorcontrib><creatorcontrib>Daub, Jörg</creatorcontrib><title>An Ionically Driven Molecular IMPLICATION Gate Operating in Fluorescence Mode</title><title>Chemistry : a European journal</title><addtitle>Chemistry - A European Journal</addtitle><description>An asymmetrically core‐extended boron–dipyrromethene (BDP) dye was equipped with two electron‐donating macrocyclic binding units with different metal ion preferences to operate as an ionically driven molecular IMPLICATION gate. A Na+‐responsive tetraoxa‐aza crown ether (R2) was integrated into the extended π system of the BDP chromophore to trigger strong intramolecular charge transfer (ICT2) fluorescence and guarantee cation‐induced spectral shifts in absorption. A dithia‐oxa‐aza crown (R1) that responds to Ag+ was attached to the meso position of BDP in an electronically decoupled fashion to independently control a second ICT1 process of a quenching nature. The bifunctional molecule is designed in such a way that in the absence of both inputs, ICT1 does not compete with ICT2 and a high fluorescence output is obtained (InA=InB=0→Out=1). Accordingly, binding of only Ag+ at R1 (InA=1, InB=0) as well as complexation of both receptors (InA=InB=1) also yields Out=1. Only for the case in which Na+ is bound at R2 and R1 is in its free state does quenching occur, which is the distinguishing characteristic for the InA=0 and InB=1→Out=0 state that is required for a logic IMPLICATION gate and Boolean operations such as IF‐THEN or NOT.
Ein am Kern unsymmetrisch verlängerter Bordipyrromethen‐(BDP) Farbstoff wurde mit zwei Elektronen schiebenden makrozyklischen Bindungseinheiten, die sich in ihren Metallionenpräferenzen unterscheiden, versehen, um als molekulares IMPLICATION‐Gatter zu fungieren. Um eine starke intramolekulare Ladungstransfer‐ (intramolecular charge transfer, ICT2) Fluoreszenz zu generieren und Kationen induzierte spektrale Verschiebungen in Absorption zu garantieren, wurde ein auf Na+ ansprechender Tetraoxa‐aza‐Kronenether R2 in das verlängerte π‐System des BDP‐Chromophors integriert. Ein Dithia‐oxa‐aza‐Kronenether R1, welcher auf Ag+ anspricht, wurde an der meso‐Position des BDP‐Körpers in einer elektronisch entkoppelten Art und Weise eingeführt, um unabhängig von ICT2 einen zweiten, die Fluoreszenz löschenden ICT1 kontrollieren zu können. Das bifunktionelle Molekül wurde so konstruiert, dass ICT1 in der Abwesenheit beider Eingabeparameter nicht mit ICT2 konkurrieren kann und ein intensives Fluoreszenzsignal ausgegeben wird (InA= InB=0→Out=1). Dementsprechend führt die alleinige Bindung von Ag+ an R1 (InA=1, InB=0) sowie die Komplexierung beider Rezeptoren (InA=InB=1) ebenfalls zu Out=1. Nur wenn Na+ an R2 gebunden wird und R1 in freiem Zustand vorliegt, erfolgt Fluoreszenzlöschung. Letzteres zeichnet den charakteristischen Zustand InA=0, InB=1→Out=0 aus, der für das logische IMPLICATION‐Gatter und Boolesche Operationen wie IF‐THEN oder NOT benötigt wird.
Fluorescent gates: A molecular IMPLICATION gate has been developed through the combination of two electronically decoupled charge‐transfer (CT) processes in an asymmetrically core‐extended boron–dipyrromethene (BDP) dye when both donors D1,2 carry different cation receptors. D1 is only an active quencher when D2 is bound (input 0/1) and a high fluorescence output at >700 nm is obtained for all other input cases (see scheme).</description><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - chemistry</subject><subject>charge transfer</subject><subject>dyes/pigments</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Ions - chemistry</subject><subject>logic gates</subject><subject>molecular devices</subject><subject>Molecular Structure</subject><subject>Porphobilinogen - analogs & derivatives</subject><subject>Porphobilinogen - chemistry</subject><subject>Quantum Theory</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkDtPG0EURkcRKDgkbUq0Fd06d3beJRj8kGxMYYlyNJ69GxbGu2bGC_G_zyJbJB3Vbc53dHUI-UlhSAGKX_4RN8MCQAFoob-QARUFzZmS4oQMwHCVS8HMGfmW0hMAGMnYV3JGlQLBCj0gi6smm7VN7V0I--wm1q_YZIs2oO-Ci9lscT-fja5Ws-VdNnE7zJZbjG5XN7-zusnGoWsjJo-Nx35U4ndyWrmQ8MfxnpPV-HY1mubz5aTXzHPPtdI5p9zwQghRofGcM1WtSwBfOC3XpRAa16UR0mjqK20046C85MwrFMilRHZOLg_abWxfOkw7u6n7L0JwDbZdslJzAZxCDw4PoI9tShEru431xsW9pWDf-9n3fvajXz-4OJq79QbLf_gxWA-YA_BWB9x_orOj6e3if3l-2NZph38-ti4-W6mYEvbhbmKn99f8Qazmdsz-Ai8XiYs</recordid><startdate>20070101</startdate><enddate>20070101</enddate><creator>Rurack, Knut</creator><creator>Trieflinger, Christian</creator><creator>Koval'chuck, Anton</creator><creator>Daub, Jörg</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</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>20070101</creationdate><title>An Ionically Driven Molecular IMPLICATION Gate Operating in Fluorescence Mode</title><author>Rurack, Knut ; Trieflinger, Christian ; Koval'chuck, Anton ; Daub, Jörg</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4878-414942555fe9c4437fbd00c2a86bd558ebd956981cf8983407c643c7e5e466e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - chemistry</topic><topic>charge transfer</topic><topic>dyes/pigments</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Ions - chemistry</topic><topic>logic gates</topic><topic>molecular devices</topic><topic>Molecular Structure</topic><topic>Porphobilinogen - analogs & derivatives</topic><topic>Porphobilinogen - chemistry</topic><topic>Quantum Theory</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rurack, Knut</creatorcontrib><creatorcontrib>Trieflinger, Christian</creatorcontrib><creatorcontrib>Koval'chuck, Anton</creatorcontrib><creatorcontrib>Daub, Jörg</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>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rurack, Knut</au><au>Trieflinger, Christian</au><au>Koval'chuck, Anton</au><au>Daub, Jörg</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Ionically Driven Molecular IMPLICATION Gate Operating in Fluorescence Mode</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry - A European Journal</addtitle><date>2007-01-01</date><risdate>2007</risdate><volume>13</volume><issue>32</issue><spage>8998</spage><epage>9003</epage><pages>8998-9003</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>An asymmetrically core‐extended boron–dipyrromethene (BDP) dye was equipped with two electron‐donating macrocyclic binding units with different metal ion preferences to operate as an ionically driven molecular IMPLICATION gate. A Na+‐responsive tetraoxa‐aza crown ether (R2) was integrated into the extended π system of the BDP chromophore to trigger strong intramolecular charge transfer (ICT2) fluorescence and guarantee cation‐induced spectral shifts in absorption. A dithia‐oxa‐aza crown (R1) that responds to Ag+ was attached to the meso position of BDP in an electronically decoupled fashion to independently control a second ICT1 process of a quenching nature. The bifunctional molecule is designed in such a way that in the absence of both inputs, ICT1 does not compete with ICT2 and a high fluorescence output is obtained (InA=InB=0→Out=1). Accordingly, binding of only Ag+ at R1 (InA=1, InB=0) as well as complexation of both receptors (InA=InB=1) also yields Out=1. Only for the case in which Na+ is bound at R2 and R1 is in its free state does quenching occur, which is the distinguishing characteristic for the InA=0 and InB=1→Out=0 state that is required for a logic IMPLICATION gate and Boolean operations such as IF‐THEN or NOT.
Ein am Kern unsymmetrisch verlängerter Bordipyrromethen‐(BDP) Farbstoff wurde mit zwei Elektronen schiebenden makrozyklischen Bindungseinheiten, die sich in ihren Metallionenpräferenzen unterscheiden, versehen, um als molekulares IMPLICATION‐Gatter zu fungieren. Um eine starke intramolekulare Ladungstransfer‐ (intramolecular charge transfer, ICT2) Fluoreszenz zu generieren und Kationen induzierte spektrale Verschiebungen in Absorption zu garantieren, wurde ein auf Na+ ansprechender Tetraoxa‐aza‐Kronenether R2 in das verlängerte π‐System des BDP‐Chromophors integriert. Ein Dithia‐oxa‐aza‐Kronenether R1, welcher auf Ag+ anspricht, wurde an der meso‐Position des BDP‐Körpers in einer elektronisch entkoppelten Art und Weise eingeführt, um unabhängig von ICT2 einen zweiten, die Fluoreszenz löschenden ICT1 kontrollieren zu können. Das bifunktionelle Molekül wurde so konstruiert, dass ICT1 in der Abwesenheit beider Eingabeparameter nicht mit ICT2 konkurrieren kann und ein intensives Fluoreszenzsignal ausgegeben wird (InA= InB=0→Out=1). Dementsprechend führt die alleinige Bindung von Ag+ an R1 (InA=1, InB=0) sowie die Komplexierung beider Rezeptoren (InA=InB=1) ebenfalls zu Out=1. Nur wenn Na+ an R2 gebunden wird und R1 in freiem Zustand vorliegt, erfolgt Fluoreszenzlöschung. Letzteres zeichnet den charakteristischen Zustand InA=0, InB=1→Out=0 aus, der für das logische IMPLICATION‐Gatter und Boolesche Operationen wie IF‐THEN oder NOT benötigt wird.
Fluorescent gates: A molecular IMPLICATION gate has been developed through the combination of two electronically decoupled charge‐transfer (CT) processes in an asymmetrically core‐extended boron–dipyrromethene (BDP) dye when both donors D1,2 carry different cation receptors. D1 is only an active quencher when D2 is bound (input 0/1) and a high fluorescence output at >700 nm is obtained for all other input cases (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>17705328</pmid><doi>10.1002/chem.200700858</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Boron Compounds - chemical synthesis Boron Compounds - chemistry charge transfer dyes/pigments Fluorescence Fluorescent Dyes - chemistry Ions - chemistry logic gates molecular devices Molecular Structure Porphobilinogen - analogs & derivatives Porphobilinogen - chemistry Quantum Theory |
| title | An Ionically Driven Molecular IMPLICATION Gate Operating in Fluorescence Mode |
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