Homochiral [2]Catenane and Bis[2]catenane from Alleno-Acetylenic Helicates - A Highly Selective Narcissistic Self-Sorting Process

Homochiral strands of alternating alleno-acetylenes and phenanthroline ligands (P)-1 and (P 2)-2, as well as their corresponding enantiomers, selectively assemble with the addition of silver­(I) salt to yield dinuclear and trinuclear double helicates, respectively. Upon increasing the solvent polari...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2015-10, Vol.137 (39), p.12502-12505
Main Authors: Gidron, Ori, Jirásek, Michael, Trapp, Nils, Ebert, Marc-Olivier, Zhang, Xiangyang, Diederich, François
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-a390t-4a836d95b3601aac59bd9238e133542bbc330999ee61154138285bc70933373e3
cites cdi_FETCH-LOGICAL-a390t-4a836d95b3601aac59bd9238e133542bbc330999ee61154138285bc70933373e3
container_end_page 12505
container_issue 39
container_start_page 12502
container_title Journal of the American Chemical Society
container_volume 137
creator Gidron, Ori
Jirásek, Michael
Trapp, Nils
Ebert, Marc-Olivier
Zhang, Xiangyang
Diederich, François
description Homochiral strands of alternating alleno-acetylenes and phenanthroline ligands (P)-1 and (P 2)-2, as well as their corresponding enantiomers, selectively assemble with the addition of silver­(I) salt to yield dinuclear and trinuclear double helicates, respectively. Upon increasing the solvent polarity, the dinuclear and trinuclear helicates interlock to form a [2]­catenane and bis[2]­catenane, bearing 14 chirality elements, respectively. The solid-state structure of the [2]­catenane reveals a nearly perfect fit of the interlocked strands, and the ECD spectra show a significant amplification of the chiroptical properties upon catenation, indicating stabilization of the helical secondary structure. Highly selective narcissistic self-sorting was demonstrated for a racemic mixture consisting of both short and long alleno-acetylenic strands, highlighting their potential for the preparation of linear catenanes of higher order.
doi_str_mv 10.1021/jacs.5b08649
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1720452714</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1720452714</sourcerecordid><originalsourceid>FETCH-LOGICAL-a390t-4a836d95b3601aac59bd9238e133542bbc330999ee61154138285bc70933373e3</originalsourceid><addsrcrecordid>eNptkM1LAzEQxYMotn7cPEuOHtyaj81ucqxFrVBUUE8iSzad2pTspiZboUf_c1OsevE0M4_fvGEeQieUDChh9GKhTRyImsgiVzuoTwUjmaCs2EV9QgjLSlnwHjqIcZHGnEm6j3qs4JLIkvXR59g33sxt0A6_sNeR7qDVLWDdTvGljUkyP9Is-AYPnYPWZ0MD3Tp11uAxOLthIs7wEI_t29yt8SM4MJ39AHyng7Ex2tglNsmz7NGHzrZv-CF4AzEeob2ZdhGOt_UQPV9fPY3G2eT-5nY0nGSaK9JluZa8mCpR84JQrY1Q9VQxLoFyLnJW14ZzopQCKCgVOeWSSVGbkijOecmBH6Kzb99l8O8riF3V2GjAufSbX8WKlozkgpU0T-j5N2qCjzHArFoG2-iwriipNqFXm9CrbegJP906r-oGpr_wT8p_pzdbC78KbXr0f68v_ySJ_Q</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1720452714</pqid></control><display><type>article</type><title>Homochiral [2]Catenane and Bis[2]catenane from Alleno-Acetylenic Helicates - A Highly Selective Narcissistic Self-Sorting Process</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Gidron, Ori ; Jirásek, Michael ; Trapp, Nils ; Ebert, Marc-Olivier ; Zhang, Xiangyang ; Diederich, François</creator><creatorcontrib>Gidron, Ori ; Jirásek, Michael ; Trapp, Nils ; Ebert, Marc-Olivier ; Zhang, Xiangyang ; Diederich, François</creatorcontrib><description>Homochiral strands of alternating alleno-acetylenes and phenanthroline ligands (P)-1 and (P 2)-2, as well as their corresponding enantiomers, selectively assemble with the addition of silver­(I) salt to yield dinuclear and trinuclear double helicates, respectively. Upon increasing the solvent polarity, the dinuclear and trinuclear helicates interlock to form a [2]­catenane and bis[2]­catenane, bearing 14 chirality elements, respectively. The solid-state structure of the [2]­catenane reveals a nearly perfect fit of the interlocked strands, and the ECD spectra show a significant amplification of the chiroptical properties upon catenation, indicating stabilization of the helical secondary structure. Highly selective narcissistic self-sorting was demonstrated for a racemic mixture consisting of both short and long alleno-acetylenic strands, highlighting their potential for the preparation of linear catenanes of higher order.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.5b08649</identifier><identifier>PMID: 26380872</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2015-10, Vol.137 (39), p.12502-12505</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a390t-4a836d95b3601aac59bd9238e133542bbc330999ee61154138285bc70933373e3</citedby><cites>FETCH-LOGICAL-a390t-4a836d95b3601aac59bd9238e133542bbc330999ee61154138285bc70933373e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26380872$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gidron, Ori</creatorcontrib><creatorcontrib>Jirásek, Michael</creatorcontrib><creatorcontrib>Trapp, Nils</creatorcontrib><creatorcontrib>Ebert, Marc-Olivier</creatorcontrib><creatorcontrib>Zhang, Xiangyang</creatorcontrib><creatorcontrib>Diederich, François</creatorcontrib><title>Homochiral [2]Catenane and Bis[2]catenane from Alleno-Acetylenic Helicates - A Highly Selective Narcissistic Self-Sorting Process</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Homochiral strands of alternating alleno-acetylenes and phenanthroline ligands (P)-1 and (P 2)-2, as well as their corresponding enantiomers, selectively assemble with the addition of silver­(I) salt to yield dinuclear and trinuclear double helicates, respectively. Upon increasing the solvent polarity, the dinuclear and trinuclear helicates interlock to form a [2]­catenane and bis[2]­catenane, bearing 14 chirality elements, respectively. The solid-state structure of the [2]­catenane reveals a nearly perfect fit of the interlocked strands, and the ECD spectra show a significant amplification of the chiroptical properties upon catenation, indicating stabilization of the helical secondary structure. Highly selective narcissistic self-sorting was demonstrated for a racemic mixture consisting of both short and long alleno-acetylenic strands, highlighting their potential for the preparation of linear catenanes of higher order.</description><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNptkM1LAzEQxYMotn7cPEuOHtyaj81ucqxFrVBUUE8iSzad2pTspiZboUf_c1OsevE0M4_fvGEeQieUDChh9GKhTRyImsgiVzuoTwUjmaCs2EV9QgjLSlnwHjqIcZHGnEm6j3qs4JLIkvXR59g33sxt0A6_sNeR7qDVLWDdTvGljUkyP9Is-AYPnYPWZ0MD3Tp11uAxOLthIs7wEI_t29yt8SM4MJ39AHyng7Ex2tglNsmz7NGHzrZv-CF4AzEeob2ZdhGOt_UQPV9fPY3G2eT-5nY0nGSaK9JluZa8mCpR84JQrY1Q9VQxLoFyLnJW14ZzopQCKCgVOeWSSVGbkijOecmBH6Kzb99l8O8riF3V2GjAufSbX8WKlozkgpU0T-j5N2qCjzHArFoG2-iwriipNqFXm9CrbegJP906r-oGpr_wT8p_pzdbC78KbXr0f68v_ySJ_Q</recordid><startdate>20151007</startdate><enddate>20151007</enddate><creator>Gidron, Ori</creator><creator>Jirásek, Michael</creator><creator>Trapp, Nils</creator><creator>Ebert, Marc-Olivier</creator><creator>Zhang, Xiangyang</creator><creator>Diederich, François</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20151007</creationdate><title>Homochiral [2]Catenane and Bis[2]catenane from Alleno-Acetylenic Helicates - A Highly Selective Narcissistic Self-Sorting Process</title><author>Gidron, Ori ; Jirásek, Michael ; Trapp, Nils ; Ebert, Marc-Olivier ; Zhang, Xiangyang ; Diederich, François</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a390t-4a836d95b3601aac59bd9238e133542bbc330999ee61154138285bc70933373e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gidron, Ori</creatorcontrib><creatorcontrib>Jirásek, Michael</creatorcontrib><creatorcontrib>Trapp, Nils</creatorcontrib><creatorcontrib>Ebert, Marc-Olivier</creatorcontrib><creatorcontrib>Zhang, Xiangyang</creatorcontrib><creatorcontrib>Diederich, François</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gidron, Ori</au><au>Jirásek, Michael</au><au>Trapp, Nils</au><au>Ebert, Marc-Olivier</au><au>Zhang, Xiangyang</au><au>Diederich, François</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Homochiral [2]Catenane and Bis[2]catenane from Alleno-Acetylenic Helicates - A Highly Selective Narcissistic Self-Sorting Process</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2015-10-07</date><risdate>2015</risdate><volume>137</volume><issue>39</issue><spage>12502</spage><epage>12505</epage><pages>12502-12505</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Homochiral strands of alternating alleno-acetylenes and phenanthroline ligands (P)-1 and (P 2)-2, as well as their corresponding enantiomers, selectively assemble with the addition of silver­(I) salt to yield dinuclear and trinuclear double helicates, respectively. Upon increasing the solvent polarity, the dinuclear and trinuclear helicates interlock to form a [2]­catenane and bis[2]­catenane, bearing 14 chirality elements, respectively. The solid-state structure of the [2]­catenane reveals a nearly perfect fit of the interlocked strands, and the ECD spectra show a significant amplification of the chiroptical properties upon catenation, indicating stabilization of the helical secondary structure. Highly selective narcissistic self-sorting was demonstrated for a racemic mixture consisting of both short and long alleno-acetylenic strands, highlighting their potential for the preparation of linear catenanes of higher order.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26380872</pmid><doi>10.1021/jacs.5b08649</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2015-10, Vol.137 (39), p.12502-12505
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_1720452714
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Homochiral [2]Catenane and Bis[2]catenane from Alleno-Acetylenic Helicates - A Highly Selective Narcissistic Self-Sorting Process
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-30T19%3A59%3A59IST&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=Homochiral%20%5B2%5DCatenane%20and%20Bis%5B2%5Dcatenane%20from%20Alleno-Acetylenic%20Helicates%20-%20A%20Highly%20Selective%20Narcissistic%20Self-Sorting%20Process&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Gidron,%20Ori&rft.date=2015-10-07&rft.volume=137&rft.issue=39&rft.spage=12502&rft.epage=12505&rft.pages=12502-12505&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.5b08649&rft_dat=%3Cproquest_cross%3E1720452714%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a390t-4a836d95b3601aac59bd9238e133542bbc330999ee61154138285bc70933373e3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1720452714&rft_id=info:pmid/26380872&rfr_iscdi=true