On‐Surface Assembly of Hydrogen‐ and Halogen‐Bonded Supramolecular Graphyne‐Like Networks
Demonstrated here is a supramolecular approach to fabricate highly ordered monolayered hydrogen‐ and halogen‐bonded graphyne‐like two‐dimensional (2D) materials from triethynyltriazine derivatives on Au(111) and Ag(111). The 2D networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to t...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-06, Vol.59 (24), p.9549-9555 |
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| creator | Yang, Zechao Fromm, Lukas Sander, Tim Gebhardt, Julian Schaub, Tobias A. Görling, Andreas Kivala, Milan Maier, Sabine |
| description | Demonstrated here is a supramolecular approach to fabricate highly ordered monolayered hydrogen‐ and halogen‐bonded graphyne‐like two‐dimensional (2D) materials from triethynyltriazine derivatives on Au(111) and Ag(111). The 2D networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to the triazine core. The structural properties and the binding energies of the supramolecular graphynes have been investigated by scanning tunneling microscopy in combination with density‐functional theory calculations. It is revealed that the N⋅⋅⋅Br−C(sp) bonds lead to significantly stronger bonded networks compared to the hydrogen‐bonded networks. A systematic analysis of the binding energies of triethynyltriazine and triethynylbenzene derivatives further demonstrates that the X3‐synthon, which is commonly observed for bromobenzene derivatives, is weaker than the X6‐synthon for our bromotriethynyl derivatives.
The on‐surface assembly of hydrogen‐ and halogen‐bonded supramolecular graphyne‐like networks from functionalized triethynyltriazine derivatives on metal surfaces, Au(111) and Ag(111), is described. The networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to the triazine core. |
| doi_str_mv | 10.1002/anie.201916708 |
| format | Article |
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The on‐surface assembly of hydrogen‐ and halogen‐bonded supramolecular graphyne‐like networks from functionalized triethynyltriazine derivatives on metal surfaces, Au(111) and Ag(111), is described. The networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to the triazine core.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201916708</identifier><identifier>PMID: 32126147</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Binding energy ; Bonding strength ; Bromobenzene ; Derivatives ; Gold ; graphyne ; halogen bonds ; Hydrogen ; hydrogen bonds ; nanostructures ; Networks ; Scanning tunneling microscopy ; self-assembly ; Silver ; surface chemistry ; Triazine</subject><ispartof>Angewandte Chemie International Edition, 2020-06, Vol.59 (24), p.9549-9555</ispartof><rights>2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2020. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5058-1bbaa8b327513adeccf93d0acfce17cb986e0cfa3b0a7752fe5bb07fbcff91013</citedby><cites>FETCH-LOGICAL-c5058-1bbaa8b327513adeccf93d0acfce17cb986e0cfa3b0a7752fe5bb07fbcff91013</cites><orcidid>0000-0002-4960-4636 ; 0000-0001-9589-6855 ; 0000-0003-1208-1824</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%2Fanie.201916708$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201916708$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32126147$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Zechao</creatorcontrib><creatorcontrib>Fromm, Lukas</creatorcontrib><creatorcontrib>Sander, Tim</creatorcontrib><creatorcontrib>Gebhardt, Julian</creatorcontrib><creatorcontrib>Schaub, Tobias A.</creatorcontrib><creatorcontrib>Görling, Andreas</creatorcontrib><creatorcontrib>Kivala, Milan</creatorcontrib><creatorcontrib>Maier, Sabine</creatorcontrib><title>On‐Surface Assembly of Hydrogen‐ and Halogen‐Bonded Supramolecular Graphyne‐Like Networks</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Demonstrated here is a supramolecular approach to fabricate highly ordered monolayered hydrogen‐ and halogen‐bonded graphyne‐like two‐dimensional (2D) materials from triethynyltriazine derivatives on Au(111) and Ag(111). The 2D networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to the triazine core. The structural properties and the binding energies of the supramolecular graphynes have been investigated by scanning tunneling microscopy in combination with density‐functional theory calculations. It is revealed that the N⋅⋅⋅Br−C(sp) bonds lead to significantly stronger bonded networks compared to the hydrogen‐bonded networks. A systematic analysis of the binding energies of triethynyltriazine and triethynylbenzene derivatives further demonstrates that the X3‐synthon, which is commonly observed for bromobenzene derivatives, is weaker than the X6‐synthon for our bromotriethynyl derivatives.
The on‐surface assembly of hydrogen‐ and halogen‐bonded supramolecular graphyne‐like networks from functionalized triethynyltriazine derivatives on metal surfaces, Au(111) and Ag(111), is described. The networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to the triazine core.</description><subject>Binding energy</subject><subject>Bonding strength</subject><subject>Bromobenzene</subject><subject>Derivatives</subject><subject>Gold</subject><subject>graphyne</subject><subject>halogen bonds</subject><subject>Hydrogen</subject><subject>hydrogen bonds</subject><subject>nanostructures</subject><subject>Networks</subject><subject>Scanning tunneling microscopy</subject><subject>self-assembly</subject><subject>Silver</subject><subject>surface chemistry</subject><subject>Triazine</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkcFOGzEQhq2KqlDaK8dqJc6beuxs7L1UCogSpAgOwNkae8ewsFkHO1u0tz5Cn7FPwoakoT315LHmm29G-hk7Aj4CzsVXbGsaCQ4lTBTX79gBFAJyqZTcG-qxlLnSBeyzjyk9DLzWfPKB7UsBYgJjdcDwqv3989d1Fz06yqYp0cI2fRZ8NuurGO5o3c6wrbIZNtvvSWgrqrLrbhlxERpyXYMxO4-4vO9bGoB5_UjZJa2eQ3xMn9h7j02iz9v3kN1-P7s5neXzq_OL0-k8dwUvdA7WImorhSpAYkXO-VJWHJ13BMrZUk-IO4_SclSqEJ4Ka7ny1nlfAgd5yL5tvMvOLqhy1K4iNmYZ6wXG3gSszb-dtr43d-GHURI0yHIQHG8FMTx1lFbmIXSxHW42Ysx1IZR-pUYbysWQUiS_2wDcrCMx60jMLpJh4Mvfd-3wPxkMQLkBnuuG-v_ozPTy4uxN_gJ1M59u</recordid><startdate>20200608</startdate><enddate>20200608</enddate><creator>Yang, Zechao</creator><creator>Fromm, Lukas</creator><creator>Sander, Tim</creator><creator>Gebhardt, Julian</creator><creator>Schaub, Tobias A.</creator><creator>Görling, Andreas</creator><creator>Kivala, Milan</creator><creator>Maier, Sabine</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-4960-4636</orcidid><orcidid>https://orcid.org/0000-0001-9589-6855</orcidid><orcidid>https://orcid.org/0000-0003-1208-1824</orcidid></search><sort><creationdate>20200608</creationdate><title>On‐Surface Assembly of Hydrogen‐ and Halogen‐Bonded Supramolecular Graphyne‐Like Networks</title><author>Yang, Zechao ; Fromm, Lukas ; Sander, Tim ; Gebhardt, Julian ; Schaub, Tobias A. ; Görling, Andreas ; Kivala, Milan ; Maier, Sabine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5058-1bbaa8b327513adeccf93d0acfce17cb986e0cfa3b0a7752fe5bb07fbcff91013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Binding energy</topic><topic>Bonding strength</topic><topic>Bromobenzene</topic><topic>Derivatives</topic><topic>Gold</topic><topic>graphyne</topic><topic>halogen bonds</topic><topic>Hydrogen</topic><topic>hydrogen bonds</topic><topic>nanostructures</topic><topic>Networks</topic><topic>Scanning tunneling microscopy</topic><topic>self-assembly</topic><topic>Silver</topic><topic>surface chemistry</topic><topic>Triazine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Zechao</creatorcontrib><creatorcontrib>Fromm, Lukas</creatorcontrib><creatorcontrib>Sander, Tim</creatorcontrib><creatorcontrib>Gebhardt, Julian</creatorcontrib><creatorcontrib>Schaub, Tobias A.</creatorcontrib><creatorcontrib>Görling, Andreas</creatorcontrib><creatorcontrib>Kivala, Milan</creatorcontrib><creatorcontrib>Maier, Sabine</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Zechao</au><au>Fromm, Lukas</au><au>Sander, Tim</au><au>Gebhardt, Julian</au><au>Schaub, Tobias A.</au><au>Görling, Andreas</au><au>Kivala, Milan</au><au>Maier, Sabine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>On‐Surface Assembly of Hydrogen‐ and Halogen‐Bonded Supramolecular Graphyne‐Like Networks</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2020-06-08</date><risdate>2020</risdate><volume>59</volume><issue>24</issue><spage>9549</spage><epage>9555</epage><pages>9549-9555</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Demonstrated here is a supramolecular approach to fabricate highly ordered monolayered hydrogen‐ and halogen‐bonded graphyne‐like two‐dimensional (2D) materials from triethynyltriazine derivatives on Au(111) and Ag(111). The 2D networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to the triazine core. The structural properties and the binding energies of the supramolecular graphynes have been investigated by scanning tunneling microscopy in combination with density‐functional theory calculations. It is revealed that the N⋅⋅⋅Br−C(sp) bonds lead to significantly stronger bonded networks compared to the hydrogen‐bonded networks. A systematic analysis of the binding energies of triethynyltriazine and triethynylbenzene derivatives further demonstrates that the X3‐synthon, which is commonly observed for bromobenzene derivatives, is weaker than the X6‐synthon for our bromotriethynyl derivatives.
The on‐surface assembly of hydrogen‐ and halogen‐bonded supramolecular graphyne‐like networks from functionalized triethynyltriazine derivatives on metal surfaces, Au(111) and Ag(111), is described. The networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to the triazine core.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>32126147</pmid><doi>10.1002/anie.201916708</doi><tpages>7</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-4960-4636</orcidid><orcidid>https://orcid.org/0000-0001-9589-6855</orcidid><orcidid>https://orcid.org/0000-0003-1208-1824</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Binding energy Bonding strength Bromobenzene Derivatives Gold graphyne halogen bonds Hydrogen hydrogen bonds nanostructures Networks Scanning tunneling microscopy self-assembly Silver surface chemistry Triazine |
| title | On‐Surface Assembly of Hydrogen‐ and Halogen‐Bonded Supramolecular Graphyne‐Like Networks |
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