Chiral Discrimination in Photochromic Helicenes

A photoresponsive dithienylethene derivative bearing chiral pinene-based arms underwent a stereoselective photoinduced cyclization reaction to produce greater than 98% of a single diastereomer. The magnitude of the optical rotation changed as much as Δ[α]373 = 8698° upon alternate irradiation with 4...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2005-05, Vol.127 (20), p.7272-7273
Hauptverfasser: Wigglesworth, Tony J, Sud, David, Norsten, Tyler B, Lekhi, Vikram S, Branda, Neil R
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 7273
container_issue 20
container_start_page 7272
container_title Journal of the American Chemical Society
container_volume 127
creator Wigglesworth, Tony J
Sud, David
Norsten, Tyler B
Lekhi, Vikram S
Branda, Neil R
description A photoresponsive dithienylethene derivative bearing chiral pinene-based arms underwent a stereoselective photoinduced cyclization reaction to produce greater than 98% of a single diastereomer. The magnitude of the optical rotation changed as much as Δ[α]373 = 8698° upon alternate irradiation with 400 nm and greater than 434 nm light.
doi_str_mv 10.1021/ja050190j
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67839457</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67839457</sourcerecordid><originalsourceid>FETCH-LOGICAL-a447t-5a4f65285b8b181c493fc14126164dbfb7b35afdfeeb46c3cd9757a0b71abcd73</originalsourceid><addsrcrecordid>eNpt0E9LwzAABfAgipvTg19AelHwUJe0SZMepVOnDB04vYYkTVlq_8ykBf32ZqxsF08h5Mfj5QFwieAdghGalgISiFJYHoExIhEMCYqSYzCGEEYhZUk8AmfOlf6KI4ZOwQgRljJK4BhMs7WxogpmxilratOIzrRNYJpguW67Vq1tWxsVzHVllG60OwcnhaicvhjOCfh4fFhl83Dx9vSc3S9CgTHtQiJwkZCIEckkYkjhNC4Uwr4WSnAuC0llTESRF1pLnKhY5SklVEBJkZAqp_EE3OxyN7b97rXreO0b6qoSjW57xxPK4hSTLbzdQWVb56wu-Mb_Q9hfjiDfrsP363h7NYT2stb5QQ5zeHA9AOGUqAorGmXcwSUshiki3oU7Z1ynf_bvwn75YjElfLV85y-zT4jmi4y_HnKFcrxse9v47f4p-Af_1oa-</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67839457</pqid></control><display><type>article</type><title>Chiral Discrimination in Photochromic Helicenes</title><source>ACS Publications</source><creator>Wigglesworth, Tony J ; Sud, David ; Norsten, Tyler B ; Lekhi, Vikram S ; Branda, Neil R</creator><creatorcontrib>Wigglesworth, Tony J ; Sud, David ; Norsten, Tyler B ; Lekhi, Vikram S ; Branda, Neil R</creatorcontrib><description>A photoresponsive dithienylethene derivative bearing chiral pinene-based arms underwent a stereoselective photoinduced cyclization reaction to produce greater than 98% of a single diastereomer. The magnitude of the optical rotation changed as much as Δ[α]373 = 8698° upon alternate irradiation with 400 nm and greater than 434 nm light.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja050190j</identifier><identifier>PMID: 15898750</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Atomic and molecular physics ; Exact sciences and technology ; Molecular properties and interactions with photons ; Optical activity and dichroism; magnetooptical and electrooptical spectra ; Optical activity, optical rotation; circular dichroism ; Physics</subject><ispartof>Journal of the American Chemical Society, 2005-05, Vol.127 (20), p.7272-7273</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-5a4f65285b8b181c493fc14126164dbfb7b35afdfeeb46c3cd9757a0b71abcd73</citedby><cites>FETCH-LOGICAL-a447t-5a4f65285b8b181c493fc14126164dbfb7b35afdfeeb46c3cd9757a0b71abcd73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja050190j$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja050190j$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=16830915$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15898750$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wigglesworth, Tony J</creatorcontrib><creatorcontrib>Sud, David</creatorcontrib><creatorcontrib>Norsten, Tyler B</creatorcontrib><creatorcontrib>Lekhi, Vikram S</creatorcontrib><creatorcontrib>Branda, Neil R</creatorcontrib><title>Chiral Discrimination in Photochromic Helicenes</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A photoresponsive dithienylethene derivative bearing chiral pinene-based arms underwent a stereoselective photoinduced cyclization reaction to produce greater than 98% of a single diastereomer. The magnitude of the optical rotation changed as much as Δ[α]373 = 8698° upon alternate irradiation with 400 nm and greater than 434 nm light.</description><subject>Atomic and molecular physics</subject><subject>Exact sciences and technology</subject><subject>Molecular properties and interactions with photons</subject><subject>Optical activity and dichroism; magnetooptical and electrooptical spectra</subject><subject>Optical activity, optical rotation; circular dichroism</subject><subject>Physics</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpt0E9LwzAABfAgipvTg19AelHwUJe0SZMepVOnDB04vYYkTVlq_8ykBf32ZqxsF08h5Mfj5QFwieAdghGalgISiFJYHoExIhEMCYqSYzCGEEYhZUk8AmfOlf6KI4ZOwQgRljJK4BhMs7WxogpmxilratOIzrRNYJpguW67Vq1tWxsVzHVllG60OwcnhaicvhjOCfh4fFhl83Dx9vSc3S9CgTHtQiJwkZCIEckkYkjhNC4Uwr4WSnAuC0llTESRF1pLnKhY5SklVEBJkZAqp_EE3OxyN7b97rXreO0b6qoSjW57xxPK4hSTLbzdQWVb56wu-Mb_Q9hfjiDfrsP363h7NYT2stb5QQ5zeHA9AOGUqAorGmXcwSUshiki3oU7Z1ynf_bvwn75YjElfLV85y-zT4jmi4y_HnKFcrxse9v47f4p-Af_1oa-</recordid><startdate>20050525</startdate><enddate>20050525</enddate><creator>Wigglesworth, Tony J</creator><creator>Sud, David</creator><creator>Norsten, Tyler B</creator><creator>Lekhi, Vikram S</creator><creator>Branda, Neil R</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050525</creationdate><title>Chiral Discrimination in Photochromic Helicenes</title><author>Wigglesworth, Tony J ; Sud, David ; Norsten, Tyler B ; Lekhi, Vikram S ; Branda, Neil R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-5a4f65285b8b181c493fc14126164dbfb7b35afdfeeb46c3cd9757a0b71abcd73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Atomic and molecular physics</topic><topic>Exact sciences and technology</topic><topic>Molecular properties and interactions with photons</topic><topic>Optical activity and dichroism; magnetooptical and electrooptical spectra</topic><topic>Optical activity, optical rotation; circular dichroism</topic><topic>Physics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wigglesworth, Tony J</creatorcontrib><creatorcontrib>Sud, David</creatorcontrib><creatorcontrib>Norsten, Tyler B</creatorcontrib><creatorcontrib>Lekhi, Vikram S</creatorcontrib><creatorcontrib>Branda, Neil R</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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>Wigglesworth, Tony J</au><au>Sud, David</au><au>Norsten, Tyler B</au><au>Lekhi, Vikram S</au><au>Branda, Neil R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral Discrimination in Photochromic Helicenes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-05-25</date><risdate>2005</risdate><volume>127</volume><issue>20</issue><spage>7272</spage><epage>7273</epage><pages>7272-7273</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>A photoresponsive dithienylethene derivative bearing chiral pinene-based arms underwent a stereoselective photoinduced cyclization reaction to produce greater than 98% of a single diastereomer. The magnitude of the optical rotation changed as much as Δ[α]373 = 8698° upon alternate irradiation with 400 nm and greater than 434 nm light.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15898750</pmid><doi>10.1021/ja050190j</doi><tpages>2</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2005-05, Vol.127 (20), p.7272-7273
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_67839457
source ACS Publications
subjects Atomic and molecular physics
Exact sciences and technology
Molecular properties and interactions with photons
Optical activity and dichroism
magnetooptical and electrooptical spectra
Optical activity, optical rotation
circular dichroism
Physics
title Chiral Discrimination in Photochromic Helicenes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T20%3A23%3A11IST&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=Chiral%20Discrimination%20in%20Photochromic%20Helicenes&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Wigglesworth,%20Tony%20J&rft.date=2005-05-25&rft.volume=127&rft.issue=20&rft.spage=7272&rft.epage=7273&rft.pages=7272-7273&rft.issn=0002-7863&rft.eissn=1520-5126&rft.coden=JACSAT&rft_id=info:doi/10.1021/ja050190j&rft_dat=%3Cproquest_cross%3E67839457%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=67839457&rft_id=info:pmid/15898750&rfr_iscdi=true