Dimerization of Tri(4-bromophenyl)benzene by Aryl−Aryl Coupling from Solution on a Gold Surface
Monolayers of monomer 1,3,5-tri(4-bromophenyl)benzene (TBPB) and the dimerized product 3,3′′′,5,5′′′-tetra(4-bromophenyl)quaterphenyl (TBPQ) on a gold surface have been studied using ambient scanning tunneling microscopy and time-of-flight secondary ion mass spectrometry (ToF-SIMS). Molecular layers...
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| Veröffentlicht in: | Journal of the American Chemical Society 2011-03, Vol.133 (12), p.4220-4223 |
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| container_title | Journal of the American Chemical Society |
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| creator | Russell, James C Blunt, Matthew O Garfitt, Jason M Scurr, David J Alexander, Morgan Champness, Neil R Beton, Peter H |
| description | Monolayers of monomer 1,3,5-tri(4-bromophenyl)benzene (TBPB) and the dimerized product 3,3′′′,5,5′′′-tetra(4-bromophenyl)quaterphenyl (TBPQ) on a gold surface have been studied using ambient scanning tunneling microscopy and time-of-flight secondary ion mass spectrometry (ToF-SIMS). Molecular layers are prepared by allowing sessile drops of solution to dry on a gold substrate. For room-temperature deposition we observe ordered arrays of TBPB in three distinct packing arrangements. Deposition on a heated substrate leads to the formation of the dimerized product, TBPQ, through a surface-induced aryl−aryl coupling. Regions of TBPQ coexist with regions of disordered multiply linked molecules. The conversion of monomer TPBP to dimers is confirmed using ToF-SIMS. Our results demonstrate an alternative, solution-phase approach to the formation of large molecules and nanostructures by coupling reactions. |
| doi_str_mv | 10.1021/ja110837s |
| format | Article |
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Molecular layers are prepared by allowing sessile drops of solution to dry on a gold substrate. For room-temperature deposition we observe ordered arrays of TBPB in three distinct packing arrangements. Deposition on a heated substrate leads to the formation of the dimerized product, TBPQ, through a surface-induced aryl−aryl coupling. Regions of TBPQ coexist with regions of disordered multiply linked molecules. The conversion of monomer TPBP to dimers is confirmed using ToF-SIMS. 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Am. Chem. Soc</addtitle><description>Monolayers of monomer 1,3,5-tri(4-bromophenyl)benzene (TBPB) and the dimerized product 3,3′′′,5,5′′′-tetra(4-bromophenyl)quaterphenyl (TBPQ) on a gold surface have been studied using ambient scanning tunneling microscopy and time-of-flight secondary ion mass spectrometry (ToF-SIMS). Molecular layers are prepared by allowing sessile drops of solution to dry on a gold substrate. For room-temperature deposition we observe ordered arrays of TBPB in three distinct packing arrangements. Deposition on a heated substrate leads to the formation of the dimerized product, TBPQ, through a surface-induced aryl−aryl coupling. Regions of TBPQ coexist with regions of disordered multiply linked molecules. The conversion of monomer TPBP to dimers is confirmed using ToF-SIMS. Our results demonstrate an alternative, solution-phase approach to the formation of large molecules and nanostructures by coupling reactions.</description><subject>Benzene Derivatives - chemistry</subject><subject>Dimerization</subject><subject>Gold - chemistry</subject><subject>Models, Molecular</subject><subject>Solutions</subject><subject>Surface Properties</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkL1OwzAURi0EoqUw8ALICxIdAv5pbGdEBQpSJYaWOXLia0iV2JHTDOkTMPOIPAmpAp2YPl3p6OjqIHRJyS0ljN5tNKVEcdkcoTGNGYliysQxGhNCWCSV4CN01jSb_pwxRU_RiFEuiZJsjPRDUUEodnpbeIe9xetQ3MyiLPjK1x_gunKagduBA5x1-D505ffn137w3Ld1Wbh3bHsWr3zZDgqHNV740uBVG6zO4RydWF02cPG7E_T29LieP0fL18XL_H4Zaa7INoohy3NuDKPCZIrTGAxJtDaMGK2sMDLRibGGKiGoACETASAN0UolM6UU4xM0Hbx58E0TwKZ1KCodupSSdJ8pPWTq2auBrdusAnMg_7r0wPUA6LxJN74Nrn_9H9EPm-dwLQ</recordid><startdate>20110330</startdate><enddate>20110330</enddate><creator>Russell, James C</creator><creator>Blunt, Matthew O</creator><creator>Garfitt, Jason M</creator><creator>Scurr, David J</creator><creator>Alexander, Morgan</creator><creator>Champness, Neil R</creator><creator>Beton, Peter H</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20110330</creationdate><title>Dimerization of Tri(4-bromophenyl)benzene by Aryl−Aryl Coupling from Solution on a Gold Surface</title><author>Russell, James C ; Blunt, Matthew O ; Garfitt, Jason M ; Scurr, David J ; Alexander, Morgan ; Champness, Neil R ; Beton, Peter H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-5ebcc3dd216db8315ed09aad20da8f6d79a9dfd186616e6796ee7d0a889488823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Benzene Derivatives - chemistry</topic><topic>Dimerization</topic><topic>Gold - chemistry</topic><topic>Models, Molecular</topic><topic>Solutions</topic><topic>Surface Properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Russell, James C</creatorcontrib><creatorcontrib>Blunt, Matthew O</creatorcontrib><creatorcontrib>Garfitt, Jason M</creatorcontrib><creatorcontrib>Scurr, David J</creatorcontrib><creatorcontrib>Alexander, Morgan</creatorcontrib><creatorcontrib>Champness, Neil R</creatorcontrib><creatorcontrib>Beton, Peter H</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Russell, James C</au><au>Blunt, Matthew O</au><au>Garfitt, Jason M</au><au>Scurr, David J</au><au>Alexander, Morgan</au><au>Champness, Neil R</au><au>Beton, Peter H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dimerization of Tri(4-bromophenyl)benzene by Aryl−Aryl Coupling from Solution on a Gold Surface</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2011-03-30</date><risdate>2011</risdate><volume>133</volume><issue>12</issue><spage>4220</spage><epage>4223</epage><pages>4220-4223</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Monolayers of monomer 1,3,5-tri(4-bromophenyl)benzene (TBPB) and the dimerized product 3,3′′′,5,5′′′-tetra(4-bromophenyl)quaterphenyl (TBPQ) on a gold surface have been studied using ambient scanning tunneling microscopy and time-of-flight secondary ion mass spectrometry (ToF-SIMS). Molecular layers are prepared by allowing sessile drops of solution to dry on a gold substrate. For room-temperature deposition we observe ordered arrays of TBPB in three distinct packing arrangements. Deposition on a heated substrate leads to the formation of the dimerized product, TBPQ, through a surface-induced aryl−aryl coupling. Regions of TBPQ coexist with regions of disordered multiply linked molecules. The conversion of monomer TPBP to dimers is confirmed using ToF-SIMS. Our results demonstrate an alternative, solution-phase approach to the formation of large molecules and nanostructures by coupling reactions.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>21370872</pmid><doi>10.1021/ja110837s</doi><tpages>4</tpages></addata></record> |
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| source | MEDLINE; ACS Publications |
| subjects | Benzene Derivatives - chemistry Dimerization Gold - chemistry Models, Molecular Solutions Surface Properties |
| title | Dimerization of Tri(4-bromophenyl)benzene by Aryl−Aryl Coupling from Solution on a Gold Surface |
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