Chiroptical Study of Chiral Discrimination by Amino Acid Based Ionic Liquids
The chiral discrimination ability of amino acid based chiral ionic liquids is studied using chiroptical luminescence techniques. A racemic mixture of dissymmetric europium tris(2,6-pyridinedicarboxylate) complexes are dissolved in five chiral ionic liquids, including l- and d-alanine methyl ester bi...
Gespeichert in:
| Veröffentlicht in: | The journal of physical chemistry. B 2012-04, Vol.116 (16), p.4952-4958 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4958 |
|---|---|
| container_issue | 16 |
| container_start_page | 4952 |
| container_title | The journal of physical chemistry. B |
| container_volume | 116 |
| creator | Kroupa, Daniel M Brown, Christopher J Heckman, Laurel M Hopkins, Todd A |
| description | The chiral discrimination ability of amino acid based chiral ionic liquids is studied using chiroptical luminescence techniques. A racemic mixture of dissymmetric europium tris(2,6-pyridinedicarboxylate) complexes are dissolved in five chiral ionic liquids, including l- and d-alanine methyl ester bis(trifluoromethanesulfonimide), l-leucine methyl ester bis(trifluoromethanesulfonimide), l-proline methyl ester bis(trifluoromethanesulfonimide), and tetrabutylammonium l-alanate. Circularly polarized luminescence spectra are measured for the samples over the 283–323 K temperature range. Analysis of the spectroscopic results shows that the amino acid methyl ester chiral ionic liquids show discrimination with a preference (handedness) that corresponds to the stereoisomer (l- vs d-). Most of the chiral ionic liquids show enthalpically dominated discrimination, but l-leucine methyl ester bis(trifluoromethanesulfonimide) shows entropically dominated chiral discrimination. |
| doi_str_mv | 10.1021/jp300357z |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1753472028</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1753472028</sourcerecordid><originalsourceid>FETCH-LOGICAL-a348t-682ee933a25cbfb0cf43eeb6985412df4c398b44de1c58ffb09670655e5826a13</originalsourceid><addsrcrecordid>eNqFkD1PwzAQhi0EoqUw8AeQFyQYAv6OM5byVSkSAzBbjuMIV2mcxskQfj2uWjohMZzu3tOjV3cvAJcY3WFE8P2qpQhRnn4fgSnmBCWx0uP9LDASE3AWwgohwokUp2BCCBOE82wK8sWX63zbO6Nr-N4P5Qh9BbfLqB9dMJ1bu0b3zjewGOE8Cg_nxpXwQQdbwqVvnIG52wyuDOfgpNJ1sBf7PgOfz08fi9ckf3tZLuZ5oimTfSIksTajVBNuiqpApmLU2kJkkjNMyooZmsmCsdJiw2UViUykSHBuuSRCYzoDNzvftvObwYZereOltq51Y_0QFE45ZSlBRP6PsizDOE2piOjtDjWdD6GzlWrj87obFUZqm7M65BzZq73tUKxteSB_g43A9Q7QJqiVH7omBvKH0Q_tSoKL</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1499117736</pqid></control><display><type>article</type><title>Chiroptical Study of Chiral Discrimination by Amino Acid Based Ionic Liquids</title><source>ACS Publications</source><source>MEDLINE</source><creator>Kroupa, Daniel M ; Brown, Christopher J ; Heckman, Laurel M ; Hopkins, Todd A</creator><creatorcontrib>Kroupa, Daniel M ; Brown, Christopher J ; Heckman, Laurel M ; Hopkins, Todd A</creatorcontrib><description>The chiral discrimination ability of amino acid based chiral ionic liquids is studied using chiroptical luminescence techniques. A racemic mixture of dissymmetric europium tris(2,6-pyridinedicarboxylate) complexes are dissolved in five chiral ionic liquids, including l- and d-alanine methyl ester bis(trifluoromethanesulfonimide), l-leucine methyl ester bis(trifluoromethanesulfonimide), l-proline methyl ester bis(trifluoromethanesulfonimide), and tetrabutylammonium l-alanate. Circularly polarized luminescence spectra are measured for the samples over the 283–323 K temperature range. Analysis of the spectroscopic results shows that the amino acid methyl ester chiral ionic liquids show discrimination with a preference (handedness) that corresponds to the stereoisomer (l- vs d-). Most of the chiral ionic liquids show enthalpically dominated discrimination, but l-leucine methyl ester bis(trifluoromethanesulfonimide) shows entropically dominated chiral discrimination.</description><identifier>ISSN: 1520-6106</identifier><identifier>EISSN: 1520-5207</identifier><identifier>DOI: 10.1021/jp300357z</identifier><identifier>PMID: 22462559</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amino acids ; Amino Acids - chemistry ; Discrimination ; Esters ; Europium ; Handedness ; Ionic liquids ; Ionic Liquids - chemistry ; Luminescence ; Luminescent Measurements ; Models, Molecular ; Molecular Structure ; Spectra</subject><ispartof>The journal of physical chemistry. B, 2012-04, Vol.116 (16), p.4952-4958</ispartof><rights>Copyright © 2012 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-682ee933a25cbfb0cf43eeb6985412df4c398b44de1c58ffb09670655e5826a13</citedby><cites>FETCH-LOGICAL-a348t-682ee933a25cbfb0cf43eeb6985412df4c398b44de1c58ffb09670655e5826a13</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/jp300357z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jp300357z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22462559$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kroupa, Daniel M</creatorcontrib><creatorcontrib>Brown, Christopher J</creatorcontrib><creatorcontrib>Heckman, Laurel M</creatorcontrib><creatorcontrib>Hopkins, Todd A</creatorcontrib><title>Chiroptical Study of Chiral Discrimination by Amino Acid Based Ionic Liquids</title><title>The journal of physical chemistry. B</title><addtitle>J. Phys. Chem. B</addtitle><description>The chiral discrimination ability of amino acid based chiral ionic liquids is studied using chiroptical luminescence techniques. A racemic mixture of dissymmetric europium tris(2,6-pyridinedicarboxylate) complexes are dissolved in five chiral ionic liquids, including l- and d-alanine methyl ester bis(trifluoromethanesulfonimide), l-leucine methyl ester bis(trifluoromethanesulfonimide), l-proline methyl ester bis(trifluoromethanesulfonimide), and tetrabutylammonium l-alanate. Circularly polarized luminescence spectra are measured for the samples over the 283–323 K temperature range. Analysis of the spectroscopic results shows that the amino acid methyl ester chiral ionic liquids show discrimination with a preference (handedness) that corresponds to the stereoisomer (l- vs d-). Most of the chiral ionic liquids show enthalpically dominated discrimination, but l-leucine methyl ester bis(trifluoromethanesulfonimide) shows entropically dominated chiral discrimination.</description><subject>Amino acids</subject><subject>Amino Acids - chemistry</subject><subject>Discrimination</subject><subject>Esters</subject><subject>Europium</subject><subject>Handedness</subject><subject>Ionic liquids</subject><subject>Ionic Liquids - chemistry</subject><subject>Luminescence</subject><subject>Luminescent Measurements</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Spectra</subject><issn>1520-6106</issn><issn>1520-5207</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkD1PwzAQhi0EoqUw8AeQFyQYAv6OM5byVSkSAzBbjuMIV2mcxskQfj2uWjohMZzu3tOjV3cvAJcY3WFE8P2qpQhRnn4fgSnmBCWx0uP9LDASE3AWwgohwokUp2BCCBOE82wK8sWX63zbO6Nr-N4P5Qh9BbfLqB9dMJ1bu0b3zjewGOE8Cg_nxpXwQQdbwqVvnIG52wyuDOfgpNJ1sBf7PgOfz08fi9ckf3tZLuZ5oimTfSIksTajVBNuiqpApmLU2kJkkjNMyooZmsmCsdJiw2UViUykSHBuuSRCYzoDNzvftvObwYZereOltq51Y_0QFE45ZSlBRP6PsizDOE2piOjtDjWdD6GzlWrj87obFUZqm7M65BzZq73tUKxteSB_g43A9Q7QJqiVH7omBvKH0Q_tSoKL</recordid><startdate>20120426</startdate><enddate>20120426</enddate><creator>Kroupa, Daniel M</creator><creator>Brown, Christopher J</creator><creator>Heckman, Laurel M</creator><creator>Hopkins, Todd A</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20120426</creationdate><title>Chiroptical Study of Chiral Discrimination by Amino Acid Based Ionic Liquids</title><author>Kroupa, Daniel M ; Brown, Christopher J ; Heckman, Laurel M ; Hopkins, Todd A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-682ee933a25cbfb0cf43eeb6985412df4c398b44de1c58ffb09670655e5826a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Amino acids</topic><topic>Amino Acids - chemistry</topic><topic>Discrimination</topic><topic>Esters</topic><topic>Europium</topic><topic>Handedness</topic><topic>Ionic liquids</topic><topic>Ionic Liquids - chemistry</topic><topic>Luminescence</topic><topic>Luminescent Measurements</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Spectra</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kroupa, Daniel M</creatorcontrib><creatorcontrib>Brown, Christopher J</creatorcontrib><creatorcontrib>Heckman, Laurel M</creatorcontrib><creatorcontrib>Hopkins, Todd A</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>The journal of physical chemistry. B</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kroupa, Daniel M</au><au>Brown, Christopher J</au><au>Heckman, Laurel M</au><au>Hopkins, Todd A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiroptical Study of Chiral Discrimination by Amino Acid Based Ionic Liquids</atitle><jtitle>The journal of physical chemistry. B</jtitle><addtitle>J. Phys. Chem. B</addtitle><date>2012-04-26</date><risdate>2012</risdate><volume>116</volume><issue>16</issue><spage>4952</spage><epage>4958</epage><pages>4952-4958</pages><issn>1520-6106</issn><eissn>1520-5207</eissn><abstract>The chiral discrimination ability of amino acid based chiral ionic liquids is studied using chiroptical luminescence techniques. A racemic mixture of dissymmetric europium tris(2,6-pyridinedicarboxylate) complexes are dissolved in five chiral ionic liquids, including l- and d-alanine methyl ester bis(trifluoromethanesulfonimide), l-leucine methyl ester bis(trifluoromethanesulfonimide), l-proline methyl ester bis(trifluoromethanesulfonimide), and tetrabutylammonium l-alanate. Circularly polarized luminescence spectra are measured for the samples over the 283–323 K temperature range. Analysis of the spectroscopic results shows that the amino acid methyl ester chiral ionic liquids show discrimination with a preference (handedness) that corresponds to the stereoisomer (l- vs d-). Most of the chiral ionic liquids show enthalpically dominated discrimination, but l-leucine methyl ester bis(trifluoromethanesulfonimide) shows entropically dominated chiral discrimination.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>22462559</pmid><doi>10.1021/jp300357z</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1520-6106 |
| ispartof | The journal of physical chemistry. B, 2012-04, Vol.116 (16), p.4952-4958 |
| issn | 1520-6106 1520-5207 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1753472028 |
| source | ACS Publications; MEDLINE |
| subjects | Amino acids Amino Acids - chemistry Discrimination Esters Europium Handedness Ionic liquids Ionic Liquids - chemistry Luminescence Luminescent Measurements Models, Molecular Molecular Structure Spectra |
| title | Chiroptical Study of Chiral Discrimination by Amino Acid Based Ionic Liquids |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-06T22%3A59%3A42IST&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=Chiroptical%20Study%20of%20Chiral%20Discrimination%20by%20Amino%20Acid%20Based%20Ionic%20Liquids&rft.jtitle=The%20journal%20of%20physical%20chemistry.%20B&rft.au=Kroupa,%20Daniel%20M&rft.date=2012-04-26&rft.volume=116&rft.issue=16&rft.spage=4952&rft.epage=4958&rft.pages=4952-4958&rft.issn=1520-6106&rft.eissn=1520-5207&rft_id=info:doi/10.1021/jp300357z&rft_dat=%3Cproquest_cross%3E1753472028%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=1499117736&rft_id=info:pmid/22462559&rfr_iscdi=true |