Sumanene Hexaester: An Electron-Deficient Buckybowl
Abstract 2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexasubstituted sumanene with CO 2 Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this...
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Veröffentlicht in: | Synthesis (Stuttgart) 2019-12, Vol.51 (24), p.4576-4581 |
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creator | Toda, Hideaki Uetake, Yuta Yakiyama, Yumi Nakazawa, Hironobu Kajitani, Takashi Fukushima, Takanori Sakurai, Hidehiro |
description | Abstract
2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexasubstituted sumanene with CO
2
Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system. |
doi_str_mv | 10.1055/s-0039-1690206 |
format | Article |
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2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexasubstituted sumanene with CO
2
Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0039-1690206</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2019-12, Vol.51 (24), p.4576-4581</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c387t-610c25bbcf58be4172b40d46b39e03c8fa9d0d1f15b7b1b752871d3f4e2ad3623</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0039-1690206.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0039-1690206$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3015,3016,27922,27923,54557,54558</link.rule.ids></links><search><creatorcontrib>Toda, Hideaki</creatorcontrib><creatorcontrib>Uetake, Yuta</creatorcontrib><creatorcontrib>Yakiyama, Yumi</creatorcontrib><creatorcontrib>Nakazawa, Hironobu</creatorcontrib><creatorcontrib>Kajitani, Takashi</creatorcontrib><creatorcontrib>Fukushima, Takanori</creatorcontrib><creatorcontrib>Sakurai, Hidehiro</creatorcontrib><title>Sumanene Hexaester: An Electron-Deficient Buckybowl</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexasubstituted sumanene with CO
2
Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1j71OwzAUhS0EEqGwMucFXO61kzhhK6VQpEoMgMRm2c61SEkTZCeCvj0t7cp0hvOj8zF2jTBFyPObyAFkxbGoQEBxwhLMpOIC4f2UJX-WKks8ZxcxrgFACVklTL6MG9NRR-mSfgzFgcJtOuvSRUtuCH3H78k3rqFuSO9G97m1_Xd7yc68aSNdHXXC3h4Wr_MlXz0_Ps1nK-5kqQZeIDiRW-t8XlrKUAmbQZ0VVlYE0pXeVDXU6DG3yqJVuSgV1tJnJEwtCyEnbHrYdaGPMZDXX6HZmLDVCHqPrKPec-kj8q7AD4Xho6EN6XU_hm738L_8LzwWVqs</recordid><startdate>20191201</startdate><enddate>20191201</enddate><creator>Toda, Hideaki</creator><creator>Uetake, Yuta</creator><creator>Yakiyama, Yumi</creator><creator>Nakazawa, Hironobu</creator><creator>Kajitani, Takashi</creator><creator>Fukushima, Takanori</creator><creator>Sakurai, Hidehiro</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20191201</creationdate><title>Sumanene Hexaester: An Electron-Deficient Buckybowl</title><author>Toda, Hideaki ; Uetake, Yuta ; Yakiyama, Yumi ; Nakazawa, Hironobu ; Kajitani, Takashi ; Fukushima, Takanori ; Sakurai, Hidehiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c387t-610c25bbcf58be4172b40d46b39e03c8fa9d0d1f15b7b1b752871d3f4e2ad3623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Toda, Hideaki</creatorcontrib><creatorcontrib>Uetake, Yuta</creatorcontrib><creatorcontrib>Yakiyama, Yumi</creatorcontrib><creatorcontrib>Nakazawa, Hironobu</creatorcontrib><creatorcontrib>Kajitani, Takashi</creatorcontrib><creatorcontrib>Fukushima, Takanori</creatorcontrib><creatorcontrib>Sakurai, Hidehiro</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Toda, Hideaki</au><au>Uetake, Yuta</au><au>Yakiyama, Yumi</au><au>Nakazawa, Hironobu</au><au>Kajitani, Takashi</au><au>Fukushima, Takanori</au><au>Sakurai, Hidehiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sumanene Hexaester: An Electron-Deficient Buckybowl</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2019-12-01</date><risdate>2019</risdate><volume>51</volume><issue>24</issue><spage>4576</spage><epage>4581</epage><pages>4576-4581</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexasubstituted sumanene with CO
2
Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0039-1690206</doi><tpages>6</tpages></addata></record> |
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title | Sumanene Hexaester: An Electron-Deficient Buckybowl |
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