On-Surface Synthesis of Heptacene Organometallic Complexes

We report the on-surface formation of Au-directed heptacene organometallic complexes on a Au(111) template in an ultrahigh vacuum environment. Successive thermal annealing steps investigated by means of scanning tunneling microscopy, noncontact atomic force microscopy, temperature-programmed desorpt...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2017-08, Vol.139 (34), p.11658-11661
Hauptverfasser: Urgel, José I, Hayashi, Hironobu, Di Giovannantonio, Marco, Pignedoli, Carlo A, Mishra, Shantanu, Deniz, Okan, Yamashita, Masataka, Dienel, Thomas, Ruffieux, Pascal, Yamada, Hiroko, Fasel, Roman
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 11661
container_issue 34
container_start_page 11658
container_title Journal of the American Chemical Society
container_volume 139
creator Urgel, José I
Hayashi, Hironobu
Di Giovannantonio, Marco
Pignedoli, Carlo A
Mishra, Shantanu
Deniz, Okan
Yamashita, Masataka
Dienel, Thomas
Ruffieux, Pascal
Yamada, Hiroko
Fasel, Roman
description We report the on-surface formation of Au-directed heptacene organometallic complexes on a Au(111) template in an ultrahigh vacuum environment. Successive thermal annealing steps investigated by means of scanning tunneling microscopy, noncontact atomic force microscopy, temperature-programmed desorption and density functional theory reveal the formation of heptacene organometallic complexes via a selective two-step activation of an α-diketone-protected heptacene precursor. Furthermore, we demonstrate the efficiency of tip-induced deprotection experiments as a complementary strategy in the complex formation. Our results provide perspectives for the on-surface synthesis of larger acenes featuring potential use in the fields of organic electronics, spintronics and nonlinear optics.
doi_str_mv 10.1021/jacs.7b05192
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1926979647</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1926979647</sourcerecordid><originalsourceid>FETCH-LOGICAL-a465t-3f2c9c113e0a78f47830cbdfb52bdcb3947dd4f7488c032e8961d0a2f6d298973</originalsourceid><addsrcrecordid>eNptkLtPwzAQhy0EoqWwMaOMDKT4kfjBhiqgSJU6FObIsc-QKi_sRGr_exK1wMJ0utN3v9N9CF0TPCeYkvutNmEucpwSRU_QlKQUxymh_BRNMcY0FpKzCboIYTu0CZXkHE2oFBJLrqboYV3Hm947bSDa7OvuE0IRosZFS2i7YVhDtPYfum4q6HRZFiZaNFVbwg7CJTpzugxwdawz9P789LZYxqv1y-vicRXrhKddzBw1yhDCAGshXSIkwya3Lk9pbk3OVCKsTZxIpDSYUZCKE4s1ddxSJZVgM3R7yG1989VD6LKqCAbKUtfQ9CEb_uZKKJ6M6N0BNb4JwYPLWl9U2u8zgrPRVjbayo62BvzmmNznFdhf-EfP3-lxa9v0vh4e_T_rG1TAcjs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1926979647</pqid></control><display><type>article</type><title>On-Surface Synthesis of Heptacene Organometallic Complexes</title><source>American Chemical Society Journals</source><creator>Urgel, José I ; Hayashi, Hironobu ; Di Giovannantonio, Marco ; Pignedoli, Carlo A ; Mishra, Shantanu ; Deniz, Okan ; Yamashita, Masataka ; Dienel, Thomas ; Ruffieux, Pascal ; Yamada, Hiroko ; Fasel, Roman</creator><creatorcontrib>Urgel, José I ; Hayashi, Hironobu ; Di Giovannantonio, Marco ; Pignedoli, Carlo A ; Mishra, Shantanu ; Deniz, Okan ; Yamashita, Masataka ; Dienel, Thomas ; Ruffieux, Pascal ; Yamada, Hiroko ; Fasel, Roman</creatorcontrib><description>We report the on-surface formation of Au-directed heptacene organometallic complexes on a Au(111) template in an ultrahigh vacuum environment. Successive thermal annealing steps investigated by means of scanning tunneling microscopy, noncontact atomic force microscopy, temperature-programmed desorption and density functional theory reveal the formation of heptacene organometallic complexes via a selective two-step activation of an α-diketone-protected heptacene precursor. Furthermore, we demonstrate the efficiency of tip-induced deprotection experiments as a complementary strategy in the complex formation. Our results provide perspectives for the on-surface synthesis of larger acenes featuring potential use in the fields of organic electronics, spintronics and nonlinear optics.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.7b05192</identifier><identifier>PMID: 28780869</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2017-08, Vol.139 (34), p.11658-11661</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a465t-3f2c9c113e0a78f47830cbdfb52bdcb3947dd4f7488c032e8961d0a2f6d298973</citedby><cites>FETCH-LOGICAL-a465t-3f2c9c113e0a78f47830cbdfb52bdcb3947dd4f7488c032e8961d0a2f6d298973</cites><orcidid>0000-0001-7608-2979 ; 0000-0001-8146-8841 ; 0000-0001-8634-8849 ; 0000-0001-5729-5354 ; 0000-0002-1553-6487 ; 0000-0002-7872-3052</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jacs.7b05192$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.7b05192$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28780869$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Urgel, José I</creatorcontrib><creatorcontrib>Hayashi, Hironobu</creatorcontrib><creatorcontrib>Di Giovannantonio, Marco</creatorcontrib><creatorcontrib>Pignedoli, Carlo A</creatorcontrib><creatorcontrib>Mishra, Shantanu</creatorcontrib><creatorcontrib>Deniz, Okan</creatorcontrib><creatorcontrib>Yamashita, Masataka</creatorcontrib><creatorcontrib>Dienel, Thomas</creatorcontrib><creatorcontrib>Ruffieux, Pascal</creatorcontrib><creatorcontrib>Yamada, Hiroko</creatorcontrib><creatorcontrib>Fasel, Roman</creatorcontrib><title>On-Surface Synthesis of Heptacene Organometallic Complexes</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>We report the on-surface formation of Au-directed heptacene organometallic complexes on a Au(111) template in an ultrahigh vacuum environment. Successive thermal annealing steps investigated by means of scanning tunneling microscopy, noncontact atomic force microscopy, temperature-programmed desorption and density functional theory reveal the formation of heptacene organometallic complexes via a selective two-step activation of an α-diketone-protected heptacene precursor. Furthermore, we demonstrate the efficiency of tip-induced deprotection experiments as a complementary strategy in the complex formation. Our results provide perspectives for the on-surface synthesis of larger acenes featuring potential use in the fields of organic electronics, spintronics and nonlinear optics.</description><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNptkLtPwzAQhy0EoqWwMaOMDKT4kfjBhiqgSJU6FObIsc-QKi_sRGr_exK1wMJ0utN3v9N9CF0TPCeYkvutNmEucpwSRU_QlKQUxymh_BRNMcY0FpKzCboIYTu0CZXkHE2oFBJLrqboYV3Hm947bSDa7OvuE0IRosZFS2i7YVhDtPYfum4q6HRZFiZaNFVbwg7CJTpzugxwdawz9P789LZYxqv1y-vicRXrhKddzBw1yhDCAGshXSIkwya3Lk9pbk3OVCKsTZxIpDSYUZCKE4s1ddxSJZVgM3R7yG1989VD6LKqCAbKUtfQ9CEb_uZKKJ6M6N0BNb4JwYPLWl9U2u8zgrPRVjbayo62BvzmmNznFdhf-EfP3-lxa9v0vh4e_T_rG1TAcjs</recordid><startdate>20170830</startdate><enddate>20170830</enddate><creator>Urgel, José I</creator><creator>Hayashi, Hironobu</creator><creator>Di Giovannantonio, Marco</creator><creator>Pignedoli, Carlo A</creator><creator>Mishra, Shantanu</creator><creator>Deniz, Okan</creator><creator>Yamashita, Masataka</creator><creator>Dienel, Thomas</creator><creator>Ruffieux, Pascal</creator><creator>Yamada, Hiroko</creator><creator>Fasel, Roman</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7608-2979</orcidid><orcidid>https://orcid.org/0000-0001-8146-8841</orcidid><orcidid>https://orcid.org/0000-0001-8634-8849</orcidid><orcidid>https://orcid.org/0000-0001-5729-5354</orcidid><orcidid>https://orcid.org/0000-0002-1553-6487</orcidid><orcidid>https://orcid.org/0000-0002-7872-3052</orcidid></search><sort><creationdate>20170830</creationdate><title>On-Surface Synthesis of Heptacene Organometallic Complexes</title><author>Urgel, José I ; Hayashi, Hironobu ; Di Giovannantonio, Marco ; Pignedoli, Carlo A ; Mishra, Shantanu ; Deniz, Okan ; Yamashita, Masataka ; Dienel, Thomas ; Ruffieux, Pascal ; Yamada, Hiroko ; Fasel, Roman</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a465t-3f2c9c113e0a78f47830cbdfb52bdcb3947dd4f7488c032e8961d0a2f6d298973</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Urgel, José I</creatorcontrib><creatorcontrib>Hayashi, Hironobu</creatorcontrib><creatorcontrib>Di Giovannantonio, Marco</creatorcontrib><creatorcontrib>Pignedoli, Carlo A</creatorcontrib><creatorcontrib>Mishra, Shantanu</creatorcontrib><creatorcontrib>Deniz, Okan</creatorcontrib><creatorcontrib>Yamashita, Masataka</creatorcontrib><creatorcontrib>Dienel, Thomas</creatorcontrib><creatorcontrib>Ruffieux, Pascal</creatorcontrib><creatorcontrib>Yamada, Hiroko</creatorcontrib><creatorcontrib>Fasel, Roman</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Urgel, José I</au><au>Hayashi, Hironobu</au><au>Di Giovannantonio, Marco</au><au>Pignedoli, Carlo A</au><au>Mishra, Shantanu</au><au>Deniz, Okan</au><au>Yamashita, Masataka</au><au>Dienel, Thomas</au><au>Ruffieux, Pascal</au><au>Yamada, Hiroko</au><au>Fasel, Roman</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>On-Surface Synthesis of Heptacene Organometallic Complexes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2017-08-30</date><risdate>2017</risdate><volume>139</volume><issue>34</issue><spage>11658</spage><epage>11661</epage><pages>11658-11661</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>We report the on-surface formation of Au-directed heptacene organometallic complexes on a Au(111) template in an ultrahigh vacuum environment. Successive thermal annealing steps investigated by means of scanning tunneling microscopy, noncontact atomic force microscopy, temperature-programmed desorption and density functional theory reveal the formation of heptacene organometallic complexes via a selective two-step activation of an α-diketone-protected heptacene precursor. Furthermore, we demonstrate the efficiency of tip-induced deprotection experiments as a complementary strategy in the complex formation. Our results provide perspectives for the on-surface synthesis of larger acenes featuring potential use in the fields of organic electronics, spintronics and nonlinear optics.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28780869</pmid><doi>10.1021/jacs.7b05192</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-7608-2979</orcidid><orcidid>https://orcid.org/0000-0001-8146-8841</orcidid><orcidid>https://orcid.org/0000-0001-8634-8849</orcidid><orcidid>https://orcid.org/0000-0001-5729-5354</orcidid><orcidid>https://orcid.org/0000-0002-1553-6487</orcidid><orcidid>https://orcid.org/0000-0002-7872-3052</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2017-08, Vol.139 (34), p.11658-11661
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_1926979647
source American Chemical Society Journals
title On-Surface Synthesis of Heptacene Organometallic Complexes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-21T11%3A12%3A41IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=On-Surface%20Synthesis%20of%20Heptacene%20Organometallic%20Complexes&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Urgel,%20Jose%CC%81%20I&rft.date=2017-08-30&rft.volume=139&rft.issue=34&rft.spage=11658&rft.epage=11661&rft.pages=11658-11661&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.7b05192&rft_dat=%3Cproquest_cross%3E1926979647%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1926979647&rft_id=info:pmid/28780869&rfr_iscdi=true