Supramolecular packing of alkyl substituted Janus face all- cis 2,3,4,5,6-pentafluorocyclohexyl motifs
This study uses X-ray crystallography, theory and Langmuir isotherm analysis to explore the conformations and molecular packing of alkyl all- 2,3,4,5,6-pentafluorocyclohexyl motifs, which are prepared by direct aryl hydrogenations from alkyl- or vinyl-pentafluoroaryl benzenes. Favoured conformations...
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| Veröffentlicht in: | Chemical science (Cambridge) 2021-07, Vol.12 (28), p.9712-9719 |
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| creator | Clark, Joshua L Taylor, Alaric Geddis, Ailsa Neyyappadath, Rifahath M Piscelli, Bruno A Yu, Cihang Cordes, David B Slawin, Alexandra M Z Cormanich, Rodrigo A Guldin, Stefan O'Hagan, David |
| description | This study uses X-ray crystallography, theory and Langmuir isotherm analysis to explore the conformations and molecular packing of alkyl all-
2,3,4,5,6-pentafluorocyclohexyl motifs, which are prepared by direct aryl hydrogenations from alkyl- or vinyl-pentafluoroaryl benzenes. Favoured conformations retain the more polar triaxial C-F bond arrangement of the all-
2,3,4,5,6-pentafluorocyclohexyl ring systems with the alkyl substituent adopting an equatorial orientation, and accommodating strong supramolecular interactions between rings. Langmuir isotherm analysis on a water subphase of a long chain fatty acid and alcohol carrying terminal all-
2,3,4,5,6-pentafluorocyclohexyl rings do not show any indication of monolayer assembly relative to their cyclohexane analogues, instead the molecules appear to aggregate and form higher molecular assemblies prior to compression. The study indicates the power and potential of this ring system as a motif for ordering supramolecular assembly. |
| doi_str_mv | 10.1039/d1sc02130c |
| format | Article |
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2,3,4,5,6-pentafluorocyclohexyl motifs, which are prepared by direct aryl hydrogenations from alkyl- or vinyl-pentafluoroaryl benzenes. Favoured conformations retain the more polar triaxial C-F bond arrangement of the all-
2,3,4,5,6-pentafluorocyclohexyl ring systems with the alkyl substituent adopting an equatorial orientation, and accommodating strong supramolecular interactions between rings. Langmuir isotherm analysis on a water subphase of a long chain fatty acid and alcohol carrying terminal all-
2,3,4,5,6-pentafluorocyclohexyl rings do not show any indication of monolayer assembly relative to their cyclohexane analogues, instead the molecules appear to aggregate and form higher molecular assemblies prior to compression. The study indicates the power and potential of this ring system as a motif for ordering supramolecular assembly.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d1sc02130c</identifier><identifier>PMID: 34349942</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Assembly ; Chemistry ; Crystallography ; Cyclohexane ; Fatty acids ; Isotherms</subject><ispartof>Chemical science (Cambridge), 2021-07, Vol.12 (28), p.9712-9719</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2021</rights><rights>This journal is © The Royal Society of Chemistry 2021 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c336t-bb80de7cea20a112ad7641085e19c8d8414f7e9b7a24f732b6f87734b96f11c03</citedby><cites>FETCH-LOGICAL-c336t-bb80de7cea20a112ad7641085e19c8d8414f7e9b7a24f732b6f87734b96f11c03</cites><orcidid>0000-0002-4413-5527 ; 0000-0002-0510-5552 ; 0000-0002-5366-9168 ; 0000-0002-9527-6418 ; 0000-0001-7659-1749 ; 0000-0001-6494-8309</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8293821/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8293821/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,724,777,781,861,882,27905,27906,53772,53774</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34349942$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Clark, Joshua L</creatorcontrib><creatorcontrib>Taylor, Alaric</creatorcontrib><creatorcontrib>Geddis, Ailsa</creatorcontrib><creatorcontrib>Neyyappadath, Rifahath M</creatorcontrib><creatorcontrib>Piscelli, Bruno A</creatorcontrib><creatorcontrib>Yu, Cihang</creatorcontrib><creatorcontrib>Cordes, David B</creatorcontrib><creatorcontrib>Slawin, Alexandra M Z</creatorcontrib><creatorcontrib>Cormanich, Rodrigo A</creatorcontrib><creatorcontrib>Guldin, Stefan</creatorcontrib><creatorcontrib>O'Hagan, David</creatorcontrib><title>Supramolecular packing of alkyl substituted Janus face all- cis 2,3,4,5,6-pentafluorocyclohexyl motifs</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>This study uses X-ray crystallography, theory and Langmuir isotherm analysis to explore the conformations and molecular packing of alkyl all-
2,3,4,5,6-pentafluorocyclohexyl motifs, which are prepared by direct aryl hydrogenations from alkyl- or vinyl-pentafluoroaryl benzenes. Favoured conformations retain the more polar triaxial C-F bond arrangement of the all-
2,3,4,5,6-pentafluorocyclohexyl ring systems with the alkyl substituent adopting an equatorial orientation, and accommodating strong supramolecular interactions between rings. Langmuir isotherm analysis on a water subphase of a long chain fatty acid and alcohol carrying terminal all-
2,3,4,5,6-pentafluorocyclohexyl rings do not show any indication of monolayer assembly relative to their cyclohexane analogues, instead the molecules appear to aggregate and form higher molecular assemblies prior to compression. The study indicates the power and potential of this ring system as a motif for ordering supramolecular assembly.</description><subject>Assembly</subject><subject>Chemistry</subject><subject>Crystallography</subject><subject>Cyclohexane</subject><subject>Fatty acids</subject><subject>Isotherms</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkUFP3DAQha0KVNDChR9QReqlqjZge5zEviChLbQgpB4oZ8txbAg4cWrHVfff4wW6oszFI803o-f3EDoi-JhgECcdiRpTAlh_QPsUM1LWFYidbU_xHjqM8QHnAiAVbT6iPWDAhGB0H9mbNAU1eGd0cioUk9KP_XhXeFso97h2RUxtnPs5zaYrrtSYYmGVNnnoykL3saBLWLJltazLyYyzsi754PVaO39v_ub9wc-9jQdo1yoXzeHru0C3F-e_Vj_K65_fL1dn16UGqOeybTnuTKONolgRQlXX1IxgXhkiNO84I8w2RrSNorkB2taWNw2wVtSWEI1hgU5f7k6pHUyns6SgnJxCP6iwll718v_J2N_LO_9HciqAZxsX6MvrgeB_JxNnOfRRG-fUaHyKklYVZ9XG1ox-foc--BTG_L0NlQ0G4CJTX18oHXyMwditGILlJkH5jdysnhNcZfjTW_lb9F9e8ASgG5Yz</recordid><startdate>20210721</startdate><enddate>20210721</enddate><creator>Clark, Joshua L</creator><creator>Taylor, Alaric</creator><creator>Geddis, Ailsa</creator><creator>Neyyappadath, Rifahath M</creator><creator>Piscelli, Bruno A</creator><creator>Yu, Cihang</creator><creator>Cordes, David B</creator><creator>Slawin, Alexandra M Z</creator><creator>Cormanich, Rodrigo A</creator><creator>Guldin, Stefan</creator><creator>O'Hagan, David</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-4413-5527</orcidid><orcidid>https://orcid.org/0000-0002-0510-5552</orcidid><orcidid>https://orcid.org/0000-0002-5366-9168</orcidid><orcidid>https://orcid.org/0000-0002-9527-6418</orcidid><orcidid>https://orcid.org/0000-0001-7659-1749</orcidid><orcidid>https://orcid.org/0000-0001-6494-8309</orcidid></search><sort><creationdate>20210721</creationdate><title>Supramolecular packing of alkyl substituted Janus face all- cis 2,3,4,5,6-pentafluorocyclohexyl motifs</title><author>Clark, Joshua L ; Taylor, Alaric ; Geddis, Ailsa ; Neyyappadath, Rifahath M ; Piscelli, Bruno A ; Yu, Cihang ; Cordes, David B ; Slawin, Alexandra M Z ; Cormanich, Rodrigo A ; Guldin, Stefan ; O'Hagan, David</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c336t-bb80de7cea20a112ad7641085e19c8d8414f7e9b7a24f732b6f87734b96f11c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Assembly</topic><topic>Chemistry</topic><topic>Crystallography</topic><topic>Cyclohexane</topic><topic>Fatty acids</topic><topic>Isotherms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Clark, Joshua L</creatorcontrib><creatorcontrib>Taylor, Alaric</creatorcontrib><creatorcontrib>Geddis, Ailsa</creatorcontrib><creatorcontrib>Neyyappadath, Rifahath M</creatorcontrib><creatorcontrib>Piscelli, Bruno A</creatorcontrib><creatorcontrib>Yu, Cihang</creatorcontrib><creatorcontrib>Cordes, David B</creatorcontrib><creatorcontrib>Slawin, Alexandra M Z</creatorcontrib><creatorcontrib>Cormanich, Rodrigo A</creatorcontrib><creatorcontrib>Guldin, Stefan</creatorcontrib><creatorcontrib>O'Hagan, David</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Clark, Joshua L</au><au>Taylor, Alaric</au><au>Geddis, Ailsa</au><au>Neyyappadath, Rifahath M</au><au>Piscelli, Bruno A</au><au>Yu, Cihang</au><au>Cordes, David B</au><au>Slawin, Alexandra M Z</au><au>Cormanich, Rodrigo A</au><au>Guldin, Stefan</au><au>O'Hagan, David</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Supramolecular packing of alkyl substituted Janus face all- cis 2,3,4,5,6-pentafluorocyclohexyl motifs</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2021-07-21</date><risdate>2021</risdate><volume>12</volume><issue>28</issue><spage>9712</spage><epage>9719</epage><pages>9712-9719</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>This study uses X-ray crystallography, theory and Langmuir isotherm analysis to explore the conformations and molecular packing of alkyl all-
2,3,4,5,6-pentafluorocyclohexyl motifs, which are prepared by direct aryl hydrogenations from alkyl- or vinyl-pentafluoroaryl benzenes. Favoured conformations retain the more polar triaxial C-F bond arrangement of the all-
2,3,4,5,6-pentafluorocyclohexyl ring systems with the alkyl substituent adopting an equatorial orientation, and accommodating strong supramolecular interactions between rings. Langmuir isotherm analysis on a water subphase of a long chain fatty acid and alcohol carrying terminal all-
2,3,4,5,6-pentafluorocyclohexyl rings do not show any indication of monolayer assembly relative to their cyclohexane analogues, instead the molecules appear to aggregate and form higher molecular assemblies prior to compression. The study indicates the power and potential of this ring system as a motif for ordering supramolecular assembly.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34349942</pmid><doi>10.1039/d1sc02130c</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-4413-5527</orcidid><orcidid>https://orcid.org/0000-0002-0510-5552</orcidid><orcidid>https://orcid.org/0000-0002-5366-9168</orcidid><orcidid>https://orcid.org/0000-0002-9527-6418</orcidid><orcidid>https://orcid.org/0000-0001-7659-1749</orcidid><orcidid>https://orcid.org/0000-0001-6494-8309</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Assembly Chemistry Crystallography Cyclohexane Fatty acids Isotherms |
| title | Supramolecular packing of alkyl substituted Janus face all- cis 2,3,4,5,6-pentafluorocyclohexyl motifs |
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