Perfluoroalkyl-annelated conjugated systems toward n-type organic semiconductors
The syntheses of perfluoroalkyl-annelated conjugated units: hexafluorocyclopenta[ ]thiophene, 4,4-difluoro-4 -cyclopenta[2,1- :3,4- ']dithiophene, and 6,6,12,12-tetrafluoroindeno[3,2- ]fluorine, and these-containing oligomers have been accomplished. The annelation of the perfluoroalkyl groups e...
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| Veröffentlicht in: | Pure and applied chemistry 2008-03, Vol.80 (3), p.589-597 |
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| container_title | Pure and applied chemistry |
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| creator | Ie, Yutaka Umemoto, Yoshikazu Nitani, Masashi Aso, Yoshio |
| description | The syntheses of perfluoroalkyl-annelated conjugated units: hexafluorocyclopenta[
]thiophene, 4,4-difluoro-4
-cyclopenta[2,1-
:3,4-
']dithiophene, and 6,6,12,12-tetrafluoroindeno[3,2-
]fluorine, and these-containing oligomers have been accomplished. The annelation of the perfluoroalkyl groups effectively lowers the lowest unoccupied molecular orbitral (LUMO) energy levels without disrupting the effective conjugation of the backbones, which was unambiguously clarified by spectroscopic and electrochemical measurements as well as X-ray analysis. The perfluoroalkyl-annelated oligothiophenes exhibited n-type semiconducting behavior with field-effect electron mobility up to 0.018 cm
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s |
| doi_str_mv | 10.1351/pac200880030589 |
| format | Article |
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]thiophene, 4,4-difluoro-4
-cyclopenta[2,1-
:3,4-
']dithiophene, and 6,6,12,12-tetrafluoroindeno[3,2-
]fluorine, and these-containing oligomers have been accomplished. The annelation of the perfluoroalkyl groups effectively lowers the lowest unoccupied molecular orbitral (LUMO) energy levels without disrupting the effective conjugation of the backbones, which was unambiguously clarified by spectroscopic and electrochemical measurements as well as X-ray analysis. The perfluoroalkyl-annelated oligothiophenes exhibited n-type semiconducting behavior with field-effect electron mobility up to 0.018 cm
V
s</description><identifier>ISSN: 0033-4545</identifier><identifier>EISSN: 1365-3075</identifier><identifier>DOI: 10.1351/pac200880030589</identifier><language>eng</language><publisher>Berlin: De Gruyter</publisher><subject>conjugated oligomer ; Conjugation ; Disruption ; Electron mobility ; Electrons ; Energy levels ; field-effect mobility ; Fluorine ; HOMO ; LUMO ; N-type semiconductors ; OFET devices ; Oligomers ; Organic semiconductors ; Perfluoro compounds ; Perfluoroalkyl & polyfluoroalkyl substances ; X ray analysis</subject><ispartof>Pure and applied chemistry, 2008-03, Vol.80 (3), p.589-597</ispartof><rights>2013 Walter de Gruyter GmbH, Berlin/Boston</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c364t-4183ba51a730dc8b8bf5da4c83cfd0f35531c01478e3d8eca70df2fa75175fbf3</citedby><cites>FETCH-LOGICAL-c364t-4183ba51a730dc8b8bf5da4c83cfd0f35531c01478e3d8eca70df2fa75175fbf3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Ie, Yutaka</creatorcontrib><creatorcontrib>Umemoto, Yoshikazu</creatorcontrib><creatorcontrib>Nitani, Masashi</creatorcontrib><creatorcontrib>Aso, Yoshio</creatorcontrib><title>Perfluoroalkyl-annelated conjugated systems toward n-type organic semiconductors</title><title>Pure and applied chemistry</title><description>The syntheses of perfluoroalkyl-annelated conjugated units: hexafluorocyclopenta[
]thiophene, 4,4-difluoro-4
-cyclopenta[2,1-
:3,4-
']dithiophene, and 6,6,12,12-tetrafluoroindeno[3,2-
]fluorine, and these-containing oligomers have been accomplished. The annelation of the perfluoroalkyl groups effectively lowers the lowest unoccupied molecular orbitral (LUMO) energy levels without disrupting the effective conjugation of the backbones, which was unambiguously clarified by spectroscopic and electrochemical measurements as well as X-ray analysis. The perfluoroalkyl-annelated oligothiophenes exhibited n-type semiconducting behavior with field-effect electron mobility up to 0.018 cm
V
s</description><subject>conjugated oligomer</subject><subject>Conjugation</subject><subject>Disruption</subject><subject>Electron mobility</subject><subject>Electrons</subject><subject>Energy levels</subject><subject>field-effect mobility</subject><subject>Fluorine</subject><subject>HOMO</subject><subject>LUMO</subject><subject>N-type semiconductors</subject><subject>OFET devices</subject><subject>Oligomers</subject><subject>Organic semiconductors</subject><subject>Perfluoro compounds</subject><subject>Perfluoroalkyl & polyfluoroalkyl substances</subject><subject>X ray analysis</subject><issn>0033-4545</issn><issn>1365-3075</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNp1kM1LAzEUxIMoWKtnrwueY1_2Jd304EGKX1CwBz0v2XwsrdvNmmQp-9-7tYIgeHrDY34zMIRcM7hlKNisUzoHkBIAQcjFCZkwnAuKUIhTMhm_SLng4pxcxLgFAL7g-YSs1za4pvfBq-ZjaKhqW9uoZE2mfbvt628Zh5jsLmbJ71UwWUvT0NnMh1q1G51Fu9uMZtPr5EO8JGdONdFe_dwpeX98eFs-09Xr08vyfkU1znminEmslGCqQDBaVrJywiiuJWpnwKEQyDQwXkiLRlqtCjAud6oQrBCucjglN8fcLvjP3sZUbn0f2rGyzHMEJmHB56NrdnTp4GMM1pVd2OxUGEoG5WG28s9sI3F3JPaqSTYYW4d-GMVv_D-kBDzwXz30da4</recordid><startdate>20080301</startdate><enddate>20080301</enddate><creator>Ie, Yutaka</creator><creator>Umemoto, Yoshikazu</creator><creator>Nitani, Masashi</creator><creator>Aso, Yoshio</creator><general>De Gruyter</general><general>Walter de Gruyter GmbH</general><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope></search><sort><creationdate>20080301</creationdate><title>Perfluoroalkyl-annelated conjugated systems toward n-type organic semiconductors</title><author>Ie, Yutaka ; Umemoto, Yoshikazu ; Nitani, Masashi ; Aso, Yoshio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c364t-4183ba51a730dc8b8bf5da4c83cfd0f35531c01478e3d8eca70df2fa75175fbf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>conjugated oligomer</topic><topic>Conjugation</topic><topic>Disruption</topic><topic>Electron mobility</topic><topic>Electrons</topic><topic>Energy levels</topic><topic>field-effect mobility</topic><topic>Fluorine</topic><topic>HOMO</topic><topic>LUMO</topic><topic>N-type semiconductors</topic><topic>OFET devices</topic><topic>Oligomers</topic><topic>Organic semiconductors</topic><topic>Perfluoro compounds</topic><topic>Perfluoroalkyl & polyfluoroalkyl substances</topic><topic>X ray analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ie, Yutaka</creatorcontrib><creatorcontrib>Umemoto, Yoshikazu</creatorcontrib><creatorcontrib>Nitani, Masashi</creatorcontrib><creatorcontrib>Aso, Yoshio</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Pure and applied chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ie, Yutaka</au><au>Umemoto, Yoshikazu</au><au>Nitani, Masashi</au><au>Aso, Yoshio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Perfluoroalkyl-annelated conjugated systems toward n-type organic semiconductors</atitle><jtitle>Pure and applied chemistry</jtitle><date>2008-03-01</date><risdate>2008</risdate><volume>80</volume><issue>3</issue><spage>589</spage><epage>597</epage><pages>589-597</pages><issn>0033-4545</issn><eissn>1365-3075</eissn><abstract>The syntheses of perfluoroalkyl-annelated conjugated units: hexafluorocyclopenta[
]thiophene, 4,4-difluoro-4
-cyclopenta[2,1-
:3,4-
']dithiophene, and 6,6,12,12-tetrafluoroindeno[3,2-
]fluorine, and these-containing oligomers have been accomplished. The annelation of the perfluoroalkyl groups effectively lowers the lowest unoccupied molecular orbitral (LUMO) energy levels without disrupting the effective conjugation of the backbones, which was unambiguously clarified by spectroscopic and electrochemical measurements as well as X-ray analysis. The perfluoroalkyl-annelated oligothiophenes exhibited n-type semiconducting behavior with field-effect electron mobility up to 0.018 cm
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| source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | conjugated oligomer Conjugation Disruption Electron mobility Electrons Energy levels field-effect mobility Fluorine HOMO LUMO N-type semiconductors OFET devices Oligomers Organic semiconductors Perfluoro compounds Perfluoroalkyl & polyfluoroalkyl substances X ray analysis |
| title | Perfluoroalkyl-annelated conjugated systems toward n-type organic semiconductors |
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