A Quintuple [6]Helicene with a Corannulene Core as a C 5 ‐Symmetric Propeller‐Shaped π‐System

The synthesis and structural analysis of a quintuple [6]helicene with a corannulene core is reported. The compound was synthesized from corannulene in three steps including a five‐fold intramolecular direct arylation. X‐ray crystallographic analysis revealed a C 5 ‐symmetric propeller‐shaped structu...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2018-01, Vol.130 (5), p.1351-1355
Main Authors: Kato, Kenta, Segawa, Yasutomo, Scott, Lawrence T., Itami, Kenichiro
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c845-b0c38fa0c712b2c44bb3218858a664187e306b1f35af45448117b70e9bcc325c3
cites cdi_FETCH-LOGICAL-c845-b0c38fa0c712b2c44bb3218858a664187e306b1f35af45448117b70e9bcc325c3
container_end_page 1355
container_issue 5
container_start_page 1351
container_title Angewandte Chemie
container_volume 130
creator Kato, Kenta
Segawa, Yasutomo
Scott, Lawrence T.
Itami, Kenichiro
description The synthesis and structural analysis of a quintuple [6]helicene with a corannulene core is reported. The compound was synthesized from corannulene in three steps including a five‐fold intramolecular direct arylation. X‐ray crystallographic analysis revealed a C 5 ‐symmetric propeller‐shaped structure and one‐dimensional alignment in the solid state. The enantiomers of the quintuple [6]helicene were successfully separated by HPLC, and the chirality of the two fractions was identified by CD spectroscopy. A kinetic study yielded a racemization barrier of 34.2 kcal mol −1 , which is slightly lower than that of pristine [6]helicene. DFT calculations indicate a rapid bowl‐to‐bowl inversion of the corannulene moiety and a step‐by‐step chiral inversion pathway for the five [6]helicene moieties.
doi_str_mv 10.1002/ange.201711985
format article
fullrecord <record><control><sourceid>crossref</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ange_201711985</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1002_ange_201711985</sourcerecordid><originalsourceid>FETCH-LOGICAL-c845-b0c38fa0c712b2c44bb3218858a664187e306b1f35af45448117b70e9bcc325c3</originalsourceid><addsrcrecordid>eNo9kM1Kw0AUhQdRsFa3rucFUu-dn8xkWYraQkHF7kTCzPTGRpI0TFKkuz6Cb-Y7-CQaFVfn8HE4i4-xS4QJAogr17zQRAAaxMzqIzZCLTCRRptjNgJQKrFCZafsrOteASAVJhux9ZQ_7Mqm37UV8af0eU5VGagh_lb2G-74bBtd0-yqAX134q4bKNf88_D-uK9r6mMZ-H3ctlRVFAe6cS2t-cfhZ9H1VJ-zk8JVHV385Zitbq5Xs3myvLtdzKbLJFilEw9B2sJBMCi8CEp5LwVaq61LU4XWkITUYyG1K5RWyiIab4AyH4IUOsgxm_zehrjtukhF3saydnGfI-SDonxQlP8rkl-5oFx_</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A Quintuple [6]Helicene with a Corannulene Core as a C 5 ‐Symmetric Propeller‐Shaped π‐System</title><source>Wiley</source><creator>Kato, Kenta ; Segawa, Yasutomo ; Scott, Lawrence T. ; Itami, Kenichiro</creator><creatorcontrib>Kato, Kenta ; Segawa, Yasutomo ; Scott, Lawrence T. ; Itami, Kenichiro</creatorcontrib><description>The synthesis and structural analysis of a quintuple [6]helicene with a corannulene core is reported. The compound was synthesized from corannulene in three steps including a five‐fold intramolecular direct arylation. X‐ray crystallographic analysis revealed a C 5 ‐symmetric propeller‐shaped structure and one‐dimensional alignment in the solid state. The enantiomers of the quintuple [6]helicene were successfully separated by HPLC, and the chirality of the two fractions was identified by CD spectroscopy. A kinetic study yielded a racemization barrier of 34.2 kcal mol −1 , which is slightly lower than that of pristine [6]helicene. DFT calculations indicate a rapid bowl‐to‐bowl inversion of the corannulene moiety and a step‐by‐step chiral inversion pathway for the five [6]helicene moieties.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201711985</identifier><language>eng</language><ispartof>Angewandte Chemie, 2018-01, Vol.130 (5), p.1351-1355</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c845-b0c38fa0c712b2c44bb3218858a664187e306b1f35af45448117b70e9bcc325c3</citedby><cites>FETCH-LOGICAL-c845-b0c38fa0c712b2c44bb3218858a664187e306b1f35af45448117b70e9bcc325c3</cites><orcidid>0000-0001-6439-8546 ; 0000-0001-5227-7894</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27915,27916</link.rule.ids></links><search><creatorcontrib>Kato, Kenta</creatorcontrib><creatorcontrib>Segawa, Yasutomo</creatorcontrib><creatorcontrib>Scott, Lawrence T.</creatorcontrib><creatorcontrib>Itami, Kenichiro</creatorcontrib><title>A Quintuple [6]Helicene with a Corannulene Core as a C 5 ‐Symmetric Propeller‐Shaped π‐System</title><title>Angewandte Chemie</title><description>The synthesis and structural analysis of a quintuple [6]helicene with a corannulene core is reported. The compound was synthesized from corannulene in three steps including a five‐fold intramolecular direct arylation. X‐ray crystallographic analysis revealed a C 5 ‐symmetric propeller‐shaped structure and one‐dimensional alignment in the solid state. The enantiomers of the quintuple [6]helicene were successfully separated by HPLC, and the chirality of the two fractions was identified by CD spectroscopy. A kinetic study yielded a racemization barrier of 34.2 kcal mol −1 , which is slightly lower than that of pristine [6]helicene. DFT calculations indicate a rapid bowl‐to‐bowl inversion of the corannulene moiety and a step‐by‐step chiral inversion pathway for the five [6]helicene moieties.</description><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNo9kM1Kw0AUhQdRsFa3rucFUu-dn8xkWYraQkHF7kTCzPTGRpI0TFKkuz6Cb-Y7-CQaFVfn8HE4i4-xS4QJAogr17zQRAAaxMzqIzZCLTCRRptjNgJQKrFCZafsrOteASAVJhux9ZQ_7Mqm37UV8af0eU5VGagh_lb2G-74bBtd0-yqAX134q4bKNf88_D-uK9r6mMZ-H3ctlRVFAe6cS2t-cfhZ9H1VJ-zk8JVHV385Zitbq5Xs3myvLtdzKbLJFilEw9B2sJBMCi8CEp5LwVaq61LU4XWkITUYyG1K5RWyiIab4AyH4IUOsgxm_zehrjtukhF3saydnGfI-SDonxQlP8rkl-5oFx_</recordid><startdate>20180126</startdate><enddate>20180126</enddate><creator>Kato, Kenta</creator><creator>Segawa, Yasutomo</creator><creator>Scott, Lawrence T.</creator><creator>Itami, Kenichiro</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-6439-8546</orcidid><orcidid>https://orcid.org/0000-0001-5227-7894</orcidid></search><sort><creationdate>20180126</creationdate><title>A Quintuple [6]Helicene with a Corannulene Core as a C 5 ‐Symmetric Propeller‐Shaped π‐System</title><author>Kato, Kenta ; Segawa, Yasutomo ; Scott, Lawrence T. ; Itami, Kenichiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c845-b0c38fa0c712b2c44bb3218858a664187e306b1f35af45448117b70e9bcc325c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kato, Kenta</creatorcontrib><creatorcontrib>Segawa, Yasutomo</creatorcontrib><creatorcontrib>Scott, Lawrence T.</creatorcontrib><creatorcontrib>Itami, Kenichiro</creatorcontrib><collection>CrossRef</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kato, Kenta</au><au>Segawa, Yasutomo</au><au>Scott, Lawrence T.</au><au>Itami, Kenichiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Quintuple [6]Helicene with a Corannulene Core as a C 5 ‐Symmetric Propeller‐Shaped π‐System</atitle><jtitle>Angewandte Chemie</jtitle><date>2018-01-26</date><risdate>2018</risdate><volume>130</volume><issue>5</issue><spage>1351</spage><epage>1355</epage><pages>1351-1355</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The synthesis and structural analysis of a quintuple [6]helicene with a corannulene core is reported. The compound was synthesized from corannulene in three steps including a five‐fold intramolecular direct arylation. X‐ray crystallographic analysis revealed a C 5 ‐symmetric propeller‐shaped structure and one‐dimensional alignment in the solid state. The enantiomers of the quintuple [6]helicene were successfully separated by HPLC, and the chirality of the two fractions was identified by CD spectroscopy. A kinetic study yielded a racemization barrier of 34.2 kcal mol −1 , which is slightly lower than that of pristine [6]helicene. DFT calculations indicate a rapid bowl‐to‐bowl inversion of the corannulene moiety and a step‐by‐step chiral inversion pathway for the five [6]helicene moieties.</abstract><doi>10.1002/ange.201711985</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-6439-8546</orcidid><orcidid>https://orcid.org/0000-0001-5227-7894</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0044-8249
ispartof Angewandte Chemie, 2018-01, Vol.130 (5), p.1351-1355
issn 0044-8249
1521-3757
language eng
recordid cdi_crossref_primary_10_1002_ange_201711985
source Wiley
title A Quintuple [6]Helicene with a Corannulene Core as a C 5 ‐Symmetric Propeller‐Shaped π‐System
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-14T23%3A48%3A04IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Quintuple%20%5B6%5DHelicene%20with%20a%20Corannulene%20Core%20as%20a%20C%205%20%E2%80%90Symmetric%20Propeller%E2%80%90Shaped%20%CF%80%E2%80%90System&rft.jtitle=Angewandte%20Chemie&rft.au=Kato,%20Kenta&rft.date=2018-01-26&rft.volume=130&rft.issue=5&rft.spage=1351&rft.epage=1355&rft.pages=1351-1355&rft.issn=0044-8249&rft.eissn=1521-3757&rft_id=info:doi/10.1002/ange.201711985&rft_dat=%3Ccrossref%3E10_1002_ange_201711985%3C/crossref%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c845-b0c38fa0c712b2c44bb3218858a664187e306b1f35af45448117b70e9bcc325c3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true