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Crown-Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties
A crown‐tetrathiafulvalene electroactive receptor has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiophene monomers. The synthetic route to the monofonctionalized tetrathiafulvalene (TTF) ligand has been optimized. Two derivatives of pyrrole (N‐ and 3‐substituted) wer...
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| Published in: | Chemistry : a European journal 2004-12, Vol.10 (24), p.6497-6509 |
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| container_title | Chemistry : a European journal |
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| creator | Trippé, Gaëlle Le Derf, Franck Lyskawa, Joël Mazari, Miloud Roncali, Jean Gorgues, Alain Levillain, Eric Sallé, Marc |
| description | A crown‐tetrathiafulvalene electroactive receptor has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiophene monomers. The synthetic route to the monofonctionalized tetrathiafulvalene (TTF) ligand has been optimized. Two derivatives of pyrrole (N‐ and 3‐substituted) were synthesized. The various substituted monomers have been electropolymerized to produce polypyrrole (PP) and poly(ethylenedioxothiophene) (PEDOT) films bearing the electroactive TTF moiety. The electroactivity of the polymer films is efficiently controlled by the well‐defined two‐step redox behavior of the TTF unit. In the case of PEDOT, an alternative post‐polymerization derivatization strategy has been used, involving the grafting of the crown‐TTF ligand on the previously grown PEDOT backbone. Though chemical derivatization is realized under heterogeneous conditions, in the bulk of the film, this strategy proved to be particularly efficient. These electrodes constitute the first examples of conducting polymer‐based modified electrodes incorporating a TTF electrochemical probe, able to interact with a guest ion, such as Ba2+. The cation recognition properties of these various electrodes have been analyzed by cyclic voltammetry and their electroactivity in water as well as their regeneration capability have been investigated.
An electroactive receptor consisting of a crown‐tetrathiafulvalene (TTF) unit has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiopene monomers. These systems have been electropolymerized and the resulting modified electrodes have been electrochemically characterized. The electrodes constitute the first example of conducting polymer‐based modified electrodes incorporating a TTF redox probe, able to interact with a guest ion, such as Ba2+ (see scheme). |
| doi_str_mv | 10.1002/chem.200400303 |
| format | article |
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An electroactive receptor consisting of a crown‐tetrathiafulvalene (TTF) unit has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiopene monomers. These systems have been electropolymerized and the resulting modified electrodes have been electrochemically characterized. The electrodes constitute the first example of conducting polymer‐based modified electrodes incorporating a TTF redox probe, able to interact with a guest ion, such as Ba2+ (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.200400303</identifier><identifier>PMID: 15540271</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Chemical Sciences ; crown compounds ; cyclic voltammetry ; electrochemistry ; Material chemistry ; polypyrrole ; tetrathiafulvalene</subject><ispartof>Chemistry : a European journal, 2004-12, Vol.10 (24), p.6497-6509</ispartof><rights>Copyright © 2004 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4813-cf0faf03461fe9a67a19946a89f8644c897c6d7263f8ec9230e27e87e88cf0513</citedby><cites>FETCH-LOGICAL-c4813-cf0faf03461fe9a67a19946a89f8644c897c6d7263f8ec9230e27e87e88cf0513</cites><orcidid>0000-0003-4601-6334 ; 0000-0001-7268-5342 ; 0000-0001-5322-7434 ; 0000-0002-3429-0355</orcidid></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.200400303$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.200400303$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,315,786,790,891,27957,27958,50923,51032</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15540271$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00084438$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Trippé, Gaëlle</creatorcontrib><creatorcontrib>Le Derf, Franck</creatorcontrib><creatorcontrib>Lyskawa, Joël</creatorcontrib><creatorcontrib>Mazari, Miloud</creatorcontrib><creatorcontrib>Roncali, Jean</creatorcontrib><creatorcontrib>Gorgues, Alain</creatorcontrib><creatorcontrib>Levillain, Eric</creatorcontrib><creatorcontrib>Sallé, Marc</creatorcontrib><title>Crown-Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties</title><title>Chemistry : a European journal</title><addtitle>Chemistry - A European Journal</addtitle><description>A crown‐tetrathiafulvalene electroactive receptor has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiophene monomers. The synthetic route to the monofonctionalized tetrathiafulvalene (TTF) ligand has been optimized. Two derivatives of pyrrole (N‐ and 3‐substituted) were synthesized. The various substituted monomers have been electropolymerized to produce polypyrrole (PP) and poly(ethylenedioxothiophene) (PEDOT) films bearing the electroactive TTF moiety. The electroactivity of the polymer films is efficiently controlled by the well‐defined two‐step redox behavior of the TTF unit. In the case of PEDOT, an alternative post‐polymerization derivatization strategy has been used, involving the grafting of the crown‐TTF ligand on the previously grown PEDOT backbone. Though chemical derivatization is realized under heterogeneous conditions, in the bulk of the film, this strategy proved to be particularly efficient. These electrodes constitute the first examples of conducting polymer‐based modified electrodes incorporating a TTF electrochemical probe, able to interact with a guest ion, such as Ba2+. The cation recognition properties of these various electrodes have been analyzed by cyclic voltammetry and their electroactivity in water as well as their regeneration capability have been investigated.
An electroactive receptor consisting of a crown‐tetrathiafulvalene (TTF) unit has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiopene monomers. These systems have been electropolymerized and the resulting modified electrodes have been electrochemically characterized. The electrodes constitute the first example of conducting polymer‐based modified electrodes incorporating a TTF redox probe, able to interact with a guest ion, such as Ba2+ (see scheme).</description><subject>Chemical Sciences</subject><subject>crown compounds</subject><subject>cyclic voltammetry</subject><subject>electrochemistry</subject><subject>Material chemistry</subject><subject>polypyrrole</subject><subject>tetrathiafulvalene</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkc-LEzEYhoO4uLV69Sg5CQtOza_JTLyVWrcL1a3aZb2FOP3GRmcmNUl3HfGPN0NL9SYEQsLzPnx8L0LPKJlQQtiragvthBEiCOGEP0AjmjOa8ULmD9GIKFFkMufqHD0O4RshREnOH6FzmueCsIKO0O-Zd_ddtoboTdxaU--bO9NABwFPYzRJv8HRYYNXvfeuAew8Nh2ev7le45vOxtf4U9_FLQQbXuJ5A1X0bueavgVvf5loXZfwDf4Ilfua8OG9SgT4aCE8QWe1aQI8Pd5jdPN2vp4tsuX15dVsuswqUVKeVTWpTU24kLQGZWRhqFJCmlLVpRSiKlVRyU3BJK9LqBTjBFgBZTpliuaUj9HFwbs1jd552xrfa2esXkyXevhLmymF4OXdwL44sDvvfuwhRN3aUEHTmA7cPmhZpOXJtMcxmhzAyrsQPNQnMyV66EYP3ehTNynw_Gjef2lh8xc_lpEAdQDubQP9f3R6tpi_-1eeHbI2RPh5yhr_PU3Mi1zfvr_Un9kqv2UfmCb8D4gaqq8</recordid><startdate>20041217</startdate><enddate>20041217</enddate><creator>Trippé, Gaëlle</creator><creator>Le Derf, Franck</creator><creator>Lyskawa, Joël</creator><creator>Mazari, Miloud</creator><creator>Roncali, Jean</creator><creator>Gorgues, Alain</creator><creator>Levillain, Eric</creator><creator>Sallé, Marc</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-4601-6334</orcidid><orcidid>https://orcid.org/0000-0001-7268-5342</orcidid><orcidid>https://orcid.org/0000-0001-5322-7434</orcidid><orcidid>https://orcid.org/0000-0002-3429-0355</orcidid></search><sort><creationdate>20041217</creationdate><title>Crown-Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties</title><author>Trippé, Gaëlle ; Le Derf, Franck ; Lyskawa, Joël ; Mazari, Miloud ; Roncali, Jean ; Gorgues, Alain ; Levillain, Eric ; Sallé, Marc</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4813-cf0faf03461fe9a67a19946a89f8644c897c6d7263f8ec9230e27e87e88cf0513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Chemical Sciences</topic><topic>crown compounds</topic><topic>cyclic voltammetry</topic><topic>electrochemistry</topic><topic>Material chemistry</topic><topic>polypyrrole</topic><topic>tetrathiafulvalene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Trippé, Gaëlle</creatorcontrib><creatorcontrib>Le Derf, Franck</creatorcontrib><creatorcontrib>Lyskawa, Joël</creatorcontrib><creatorcontrib>Mazari, Miloud</creatorcontrib><creatorcontrib>Roncali, Jean</creatorcontrib><creatorcontrib>Gorgues, Alain</creatorcontrib><creatorcontrib>Levillain, Eric</creatorcontrib><creatorcontrib>Sallé, Marc</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Trippé, Gaëlle</au><au>Le Derf, Franck</au><au>Lyskawa, Joël</au><au>Mazari, Miloud</au><au>Roncali, Jean</au><au>Gorgues, Alain</au><au>Levillain, Eric</au><au>Sallé, Marc</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Crown-Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry - A European Journal</addtitle><date>2004-12-17</date><risdate>2004</risdate><volume>10</volume><issue>24</issue><spage>6497</spage><epage>6509</epage><pages>6497-6509</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><notes>ark:/67375/WNG-X2P5W2Q2-0</notes><notes>istex:4FAEBBF19773723AD455B05E24E32353473C8227</notes><notes>ArticleID:CHEM200400303</notes><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A crown‐tetrathiafulvalene electroactive receptor has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiophene monomers. The synthetic route to the monofonctionalized tetrathiafulvalene (TTF) ligand has been optimized. Two derivatives of pyrrole (N‐ and 3‐substituted) were synthesized. The various substituted monomers have been electropolymerized to produce polypyrrole (PP) and poly(ethylenedioxothiophene) (PEDOT) films bearing the electroactive TTF moiety. The electroactivity of the polymer films is efficiently controlled by the well‐defined two‐step redox behavior of the TTF unit. In the case of PEDOT, an alternative post‐polymerization derivatization strategy has been used, involving the grafting of the crown‐TTF ligand on the previously grown PEDOT backbone. Though chemical derivatization is realized under heterogeneous conditions, in the bulk of the film, this strategy proved to be particularly efficient. These electrodes constitute the first examples of conducting polymer‐based modified electrodes incorporating a TTF electrochemical probe, able to interact with a guest ion, such as Ba2+. The cation recognition properties of these various electrodes have been analyzed by cyclic voltammetry and their electroactivity in water as well as their regeneration capability have been investigated.
An electroactive receptor consisting of a crown‐tetrathiafulvalene (TTF) unit has been covalently linked to electropolymerizable pyrrole or 3,4‐ethylenedioxythiopene monomers. These systems have been electropolymerized and the resulting modified electrodes have been electrochemically characterized. The electrodes constitute the first example of conducting polymer‐based modified electrodes incorporating a TTF redox probe, able to interact with a guest ion, such as Ba2+ (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>15540271</pmid><doi>10.1002/chem.200400303</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0003-4601-6334</orcidid><orcidid>https://orcid.org/0000-0001-7268-5342</orcidid><orcidid>https://orcid.org/0000-0001-5322-7434</orcidid><orcidid>https://orcid.org/0000-0002-3429-0355</orcidid></addata></record> |
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| source | Wiley-Blackwell Journals |
| subjects | Chemical Sciences crown compounds cyclic voltammetry electrochemistry Material chemistry polypyrrole tetrathiafulvalene |
| title | Crown-Tetrathiafulvalenes Attached to a Pyrrole or an EDOT Unit: Synthesis, Electropolymerization and Recognition Properties |
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