Synthesis of Substituted Trinaphthylenes via Aryne Cyclotrimerization

Synthesis of Substituted Trinaphthylenes via Aryne Cyclotrimerization

The first synthesis of a series of substituted trinaphthylene derivatives via a palladium-catalyzed aryne cyclotrimerization is reported. This method provides an approach for the preparation of novel disk-shaped polycyclic aromatic hydrocarbons that self-assemble via π−π interactions and may form co...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2009-08, Vol.11 (16), p.3726-3729
Hauptverfasser: Lynett, Philip T, Maly, Kenneth E
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3729
container_issue 16
container_start_page 3726
container_title Organic letters
container_volume 11
creator Lynett, Philip T
Maly, Kenneth E
description The first synthesis of a series of substituted trinaphthylene derivatives via a palladium-catalyzed aryne cyclotrimerization is reported. This method provides an approach for the preparation of novel disk-shaped polycyclic aromatic hydrocarbons that self-assemble via π−π interactions and may form columnar liquid crystal phases. Although the trinaphthylenes prepared in this study do not exhibit columnar mesophases, variable concentration 1H NMR studies provide evidence for aggregation in solution.
doi_str_mv 10.1021/ol9013443
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67624989</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67624989</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-96a91f6993b967915b62cb6e1d48c9d53c555e5ec5c66cc80b9aa07284a8ce083</originalsourceid><addsrcrecordid>eNptkE1Lw0AQhhdRbK0e_AOSi4KH6G42u8kcS6kfUPDQeg6bzYRuSbN1dyOkv95IS714mpfh4WXmIeSW0SdGE_ZsG6CMpyk_I2MmEh5nVCTnpyzpiFx5v6GUDRu4JCMGGYOEijGZL_s2rNEbH9k6WnalDyZ0Aato5Uyrduuw7hts0UffRkVT17cYzXrd2ODMFp3Zq2Bse00uatV4vDnOCfl8ma9mb_Hi4_V9Nl3EimcQYpAKWC0BeAkyAyZKmehSIqvSXEMluBZCoEAttJRa57QEpWiW5KnKNdKcT8jDoXfn7FeHPhRb4zU2jWrRdr6QmUxSyGEAHw-gdtZ7h3WxG-5Vri8YLX6dFSdnA3t3LO3KLVZ_5FHSANwfAKV9sbGda4cf_yn6Ac4hcvU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67624989</pqid></control><display><type>article</type><title>Synthesis of Substituted Trinaphthylenes via Aryne Cyclotrimerization</title><source>ACS Publications</source><creator>Lynett, Philip T ; Maly, Kenneth E</creator><creatorcontrib>Lynett, Philip T ; Maly, Kenneth E</creatorcontrib><description>The first synthesis of a series of substituted trinaphthylene derivatives via a palladium-catalyzed aryne cyclotrimerization is reported. This method provides an approach for the preparation of novel disk-shaped polycyclic aromatic hydrocarbons that self-assemble via π−π interactions and may form columnar liquid crystal phases. Although the trinaphthylenes prepared in this study do not exhibit columnar mesophases, variable concentration 1H NMR studies provide evidence for aggregation in solution.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol9013443</identifier><identifier>PMID: 19719205</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2009-08, Vol.11 (16), p.3726-3729</ispartof><rights>Copyright © 2009 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-96a91f6993b967915b62cb6e1d48c9d53c555e5ec5c66cc80b9aa07284a8ce083</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol9013443$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol9013443$$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/19719205$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lynett, Philip T</creatorcontrib><creatorcontrib>Maly, Kenneth E</creatorcontrib><title>Synthesis of Substituted Trinaphthylenes via Aryne Cyclotrimerization</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The first synthesis of a series of substituted trinaphthylene derivatives via a palladium-catalyzed aryne cyclotrimerization is reported. This method provides an approach for the preparation of novel disk-shaped polycyclic aromatic hydrocarbons that self-assemble via π−π interactions and may form columnar liquid crystal phases. Although the trinaphthylenes prepared in this study do not exhibit columnar mesophases, variable concentration 1H NMR studies provide evidence for aggregation in solution.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNptkE1Lw0AQhhdRbK0e_AOSi4KH6G42u8kcS6kfUPDQeg6bzYRuSbN1dyOkv95IS714mpfh4WXmIeSW0SdGE_ZsG6CMpyk_I2MmEh5nVCTnpyzpiFx5v6GUDRu4JCMGGYOEijGZL_s2rNEbH9k6WnalDyZ0Aato5Uyrduuw7hts0UffRkVT17cYzXrd2ODMFp3Zq2Bse00uatV4vDnOCfl8ma9mb_Hi4_V9Nl3EimcQYpAKWC0BeAkyAyZKmehSIqvSXEMluBZCoEAttJRa57QEpWiW5KnKNdKcT8jDoXfn7FeHPhRb4zU2jWrRdr6QmUxSyGEAHw-gdtZ7h3WxG-5Vri8YLX6dFSdnA3t3LO3KLVZ_5FHSANwfAKV9sbGda4cf_yn6Ac4hcvU</recordid><startdate>20090820</startdate><enddate>20090820</enddate><creator>Lynett, Philip T</creator><creator>Maly, Kenneth E</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20090820</creationdate><title>Synthesis of Substituted Trinaphthylenes via Aryne Cyclotrimerization</title><author>Lynett, Philip T ; Maly, Kenneth E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-96a91f6993b967915b62cb6e1d48c9d53c555e5ec5c66cc80b9aa07284a8ce083</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lynett, Philip T</creatorcontrib><creatorcontrib>Maly, Kenneth E</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lynett, Philip T</au><au>Maly, Kenneth E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Substituted Trinaphthylenes via Aryne Cyclotrimerization</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2009-08-20</date><risdate>2009</risdate><volume>11</volume><issue>16</issue><spage>3726</spage><epage>3729</epage><pages>3726-3729</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The first synthesis of a series of substituted trinaphthylene derivatives via a palladium-catalyzed aryne cyclotrimerization is reported. This method provides an approach for the preparation of novel disk-shaped polycyclic aromatic hydrocarbons that self-assemble via π−π interactions and may form columnar liquid crystal phases. Although the trinaphthylenes prepared in this study do not exhibit columnar mesophases, variable concentration 1H NMR studies provide evidence for aggregation in solution.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>19719205</pmid><doi>10.1021/ol9013443</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2009-08, Vol.11 (16), p.3726-3729
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_67624989
source ACS Publications
title Synthesis of Substituted Trinaphthylenes via Aryne Cyclotrimerization
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-08T00%3A04%3A57IST&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=Synthesis%20of%20Substituted%20Trinaphthylenes%20via%20Aryne%20Cyclotrimerization&rft.jtitle=Organic%20letters&rft.au=Lynett,%20Philip%20T&rft.date=2009-08-20&rft.volume=11&rft.issue=16&rft.spage=3726&rft.epage=3729&rft.pages=3726-3729&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol9013443&rft_dat=%3Cproquest_cross%3E67624989%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=67624989&rft_id=info:pmid/19719205&rfr_iscdi=true