Oligothienylenevinylenes incorporating 3,4-ethylenedioxythiophene (EDOT) units
A new series of π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds has been synthesized by Wittig–Horner reactions from phosphonate anions carrying EDOT or bis-EDOT units. Optical and electrochemical results evidence the crucial role of the EDOT moiety...
Gespeichert in:
| Veröffentlicht in: | Tetrahedron 2005-03, Vol.61 (12), p.3045-3053 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3053 |
|---|---|
| container_issue | 12 |
| container_start_page | 3045 |
| container_title | Tetrahedron |
| container_volume | 61 |
| creator | Turbiez, Mathieu Frère, Pierre Roncali, Jean |
| description | A new series of π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds has been synthesized by Wittig–Horner reactions from phosphonate anions carrying EDOT or bis-EDOT units. Optical and electrochemical results evidence the crucial role of the EDOT moiety for modulating the electronic properties of the oligomers. The insertion of bis-EDOT unit in the middle of the molecule leads to a self-rigidification of the conjugated system due to non covalent S⋯O intramolecular interactions. The strong electron donor effect of the EDOT units explains the determining role of the relative position of the EDOT units on the localization and stabilization of the positive charges in the radical cation or dication states.
New π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds have been synthesized. Optical and electrochemical results evidence the crucial role of the EDOT moiety for modulating the electronic properties of the oligomers. |
| doi_str_mv | 10.1016/j.tet.2005.01.107 |
| format | Article |
| fullrecord | <record><control><sourceid>elsevier_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00015862v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040402005001778</els_id><sourcerecordid>S0040402005001778</sourcerecordid><originalsourceid>FETCH-LOGICAL-c331t-94f0fb365f8c292501b634faf4c4de8f878f7940898f87784fd59fb4771609693</originalsourceid><addsrcrecordid>eNp9kEFPwzAMhSMEEmPwA7j1yCRa7DZNW3GaxmBIE7uMc9SlyZqpNFMSJvbvSRniyMn2sz9L7xFyi5AgIHvYJV76JAXIE8AgFWdkhJTROKfIzskIgEJMIYVLcuXcDgAQ02xE3lad3hrfatkfO9nLgz5VF-leGLs3tva630bZPY2lb392jTZfx4CYfRum6G7-tFpPos9ee3dNLlTdOXnzW8fk_Xm-ni3i5erldTZdxiLL0McVVaA2GctVKdIqzQE3LKOqVlTQRpaqLEpVVBTKauiLkqomr9SGFgUyqFiVjcnk9LetO763-qO2R25qzRfTJR-0wWBesvSA4RZPt8Ia56xUfwACH8LjOx7C40N4HDBIRWAeT4wMJg5aWu5EiEgE71YKzxuj_6G_ARbvdto</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Oligothienylenevinylenes incorporating 3,4-ethylenedioxythiophene (EDOT) units</title><source>ScienceDirect Journals (5 years ago - present)</source><creator>Turbiez, Mathieu ; Frère, Pierre ; Roncali, Jean</creator><creatorcontrib>Turbiez, Mathieu ; Frère, Pierre ; Roncali, Jean</creatorcontrib><description>A new series of π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds has been synthesized by Wittig–Horner reactions from phosphonate anions carrying EDOT or bis-EDOT units. Optical and electrochemical results evidence the crucial role of the EDOT moiety for modulating the electronic properties of the oligomers. The insertion of bis-EDOT unit in the middle of the molecule leads to a self-rigidification of the conjugated system due to non covalent S⋯O intramolecular interactions. The strong electron donor effect of the EDOT units explains the determining role of the relative position of the EDOT units on the localization and stabilization of the positive charges in the radical cation or dication states.
New π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds have been synthesized. Optical and electrochemical results evidence the crucial role of the EDOT moiety for modulating the electronic properties of the oligomers.</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2005.01.107</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Chemical Sciences ; Conjugated linear systems ; Material chemistry ; Oligothienylenevinylenes ; Oligothiophenes ; Witti–Horner reaction</subject><ispartof>Tetrahedron, 2005-03, Vol.61 (12), p.3045-3053</ispartof><rights>2005 Elsevier Ltd</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c331t-94f0fb365f8c292501b634faf4c4de8f878f7940898f87784fd59fb4771609693</citedby><cites>FETCH-LOGICAL-c331t-94f0fb365f8c292501b634faf4c4de8f878f7940898f87784fd59fb4771609693</cites><orcidid>0000-0002-3429-0355</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2005.01.107$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttps://hal.science/hal-00015862$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Turbiez, Mathieu</creatorcontrib><creatorcontrib>Frère, Pierre</creatorcontrib><creatorcontrib>Roncali, Jean</creatorcontrib><title>Oligothienylenevinylenes incorporating 3,4-ethylenedioxythiophene (EDOT) units</title><title>Tetrahedron</title><description>A new series of π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds has been synthesized by Wittig–Horner reactions from phosphonate anions carrying EDOT or bis-EDOT units. Optical and electrochemical results evidence the crucial role of the EDOT moiety for modulating the electronic properties of the oligomers. The insertion of bis-EDOT unit in the middle of the molecule leads to a self-rigidification of the conjugated system due to non covalent S⋯O intramolecular interactions. The strong electron donor effect of the EDOT units explains the determining role of the relative position of the EDOT units on the localization and stabilization of the positive charges in the radical cation or dication states.
New π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds have been synthesized. Optical and electrochemical results evidence the crucial role of the EDOT moiety for modulating the electronic properties of the oligomers.</description><subject>Chemical Sciences</subject><subject>Conjugated linear systems</subject><subject>Material chemistry</subject><subject>Oligothienylenevinylenes</subject><subject>Oligothiophenes</subject><subject>Witti–Horner reaction</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNp9kEFPwzAMhSMEEmPwA7j1yCRa7DZNW3GaxmBIE7uMc9SlyZqpNFMSJvbvSRniyMn2sz9L7xFyi5AgIHvYJV76JAXIE8AgFWdkhJTROKfIzskIgEJMIYVLcuXcDgAQ02xE3lad3hrfatkfO9nLgz5VF-leGLs3tva630bZPY2lb392jTZfx4CYfRum6G7-tFpPos9ee3dNLlTdOXnzW8fk_Xm-ni3i5erldTZdxiLL0McVVaA2GctVKdIqzQE3LKOqVlTQRpaqLEpVVBTKauiLkqomr9SGFgUyqFiVjcnk9LetO763-qO2R25qzRfTJR-0wWBesvSA4RZPt8Ia56xUfwACH8LjOx7C40N4HDBIRWAeT4wMJg5aWu5EiEgE71YKzxuj_6G_ARbvdto</recordid><startdate>20050321</startdate><enddate>20050321</enddate><creator>Turbiez, Mathieu</creator><creator>Frère, Pierre</creator><creator>Roncali, Jean</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-3429-0355</orcidid></search><sort><creationdate>20050321</creationdate><title>Oligothienylenevinylenes incorporating 3,4-ethylenedioxythiophene (EDOT) units</title><author>Turbiez, Mathieu ; Frère, Pierre ; Roncali, Jean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c331t-94f0fb365f8c292501b634faf4c4de8f878f7940898f87784fd59fb4771609693</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemical Sciences</topic><topic>Conjugated linear systems</topic><topic>Material chemistry</topic><topic>Oligothienylenevinylenes</topic><topic>Oligothiophenes</topic><topic>Witti–Horner reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Turbiez, Mathieu</creatorcontrib><creatorcontrib>Frère, Pierre</creatorcontrib><creatorcontrib>Roncali, Jean</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Turbiez, Mathieu</au><au>Frère, Pierre</au><au>Roncali, Jean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oligothienylenevinylenes incorporating 3,4-ethylenedioxythiophene (EDOT) units</atitle><jtitle>Tetrahedron</jtitle><date>2005-03-21</date><risdate>2005</risdate><volume>61</volume><issue>12</issue><spage>3045</spage><epage>3053</epage><pages>3045-3053</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A new series of π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds has been synthesized by Wittig–Horner reactions from phosphonate anions carrying EDOT or bis-EDOT units. Optical and electrochemical results evidence the crucial role of the EDOT moiety for modulating the electronic properties of the oligomers. The insertion of bis-EDOT unit in the middle of the molecule leads to a self-rigidification of the conjugated system due to non covalent S⋯O intramolecular interactions. The strong electron donor effect of the EDOT units explains the determining role of the relative position of the EDOT units on the localization and stabilization of the positive charges in the radical cation or dication states.
New π-conjugated oligomers based on various combinations of thiophene and EDOT units and double bonds have been synthesized. Optical and electrochemical results evidence the crucial role of the EDOT moiety for modulating the electronic properties of the oligomers.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2005.01.107</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-3429-0355</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2005-03, Vol.61 (12), p.3045-3053 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_00015862v1 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Chemical Sciences Conjugated linear systems Material chemistry Oligothienylenevinylenes Oligothiophenes Witti–Horner reaction |
| title | Oligothienylenevinylenes incorporating 3,4-ethylenedioxythiophene (EDOT) units |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T19%3A22%3A57IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-elsevier_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Oligothienylenevinylenes%20incorporating%203,4-ethylenedioxythiophene%20(EDOT)%20units&rft.jtitle=Tetrahedron&rft.au=Turbiez,%20Mathieu&rft.date=2005-03-21&rft.volume=61&rft.issue=12&rft.spage=3045&rft.epage=3053&rft.pages=3045-3053&rft.issn=0040-4020&rft.eissn=1464-5416&rft_id=info:doi/10.1016/j.tet.2005.01.107&rft_dat=%3Celsevier_hal_p%3ES0040402005001778%3C/elsevier_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rft_els_id=S0040402005001778&rfr_iscdi=true |