The indium( iii ) chloride catalyzed synthesis of sulfur incorporated 3-acylcoumarins; their photochromic and acetate sensing properties
The synthesis and evaluation of the photochromic properties of 3-acylcoumarins are very important as they exhibit selective sensing properties. We found that InCl 3 efficiently catalyzes the condensation of 2-hydroxybenzaldehydes and β-keto esters to provide near quantitative yields of 3-acylcoumari...
Gespeichert in:
| Veröffentlicht in: | RSC advances 2014-01, Vol.4 (109), p.63642-63649 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 63649 |
|---|---|
| container_issue | 109 |
| container_start_page | 63642 |
| container_title | RSC advances |
| container_volume | 4 |
| creator | Prakash Rao, H. Surya Desai, Avinash |
| description | The synthesis and evaluation of the photochromic properties of 3-acylcoumarins are very important as they exhibit selective sensing properties. We found that InCl
3
efficiently catalyzes the condensation of 2-hydroxybenzaldehydes and β-keto esters to provide near quantitative yields of 3-acylcoumarins. The 3-(phenylsulfanyl/phenylsulfinyl/phenylsufonyl)propanoyl coumarins with an electron-donating NMe
2
group at the C7 position were prepared to evaluate the influence of sulfur on the emission and acetate ion sensing properties. Our studies revealed that 7-(diethylamino)-3-(3-(phenylsulfanyl/phenylsulfinyl/phenylsufonyl)propanoyl)-2
H
-chromen-2-one exhibits excellent fluorescence emission in hexane and ethyl acetate (
Φ
≈ 80%). The 3-acylcoumarin with sulfone in the C3-acyl side-chain detects acetate anions selectively and this property can be conveniently followed by fluorescence emission spectroscopy. |
| doi_str_mv | 10.1039/C4RA09228G |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1730047671</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1730047671</sourcerecordid><originalsourceid>FETCH-LOGICAL-c264t-6881fbddac9942c8b576b04f5ec40ac63f5b6568dbce2ac9975976e296664eab3</originalsourceid><addsrcrecordid>eNpNkEFLxDAQhYMouKx78RfkuArVJG3TFk_LoquwIMh6Lul0aiNtU5P0UH-BP9ssCjqXmcP33mMeIZec3XAWF7fb5GXDCiHy3QlZCJbISDBZnP67z8nKuXcWRqZcSL4gX4cWqR5qPfVrqrWmVxTazlhdIwXlVTd_Yk3dPPgWnXbUNNRNXTPZIAJjR2OVD0AcKZg7MFOvrB7cHQ24tnRsjTfQWtNroGqoqQL0QUAdDk4Pb3S0ZkTrNboLctaozuHqdy_J68P9YfsY7Z93T9vNPgIhEx_JPOdNVdcKiiIRkFdpJiuWNClCwhTIuEkrmcq8rgDFEcrSIpMoCillgqqKl2T94xuiPyZ0vuy1A-w6NaCZXMmzmLEkkxkP6PUPCtY4Z7EpR6vDg3PJWXlsvPxrPP4GPVN2FA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1730047671</pqid></control><display><type>article</type><title>The indium( iii ) chloride catalyzed synthesis of sulfur incorporated 3-acylcoumarins; their photochromic and acetate sensing properties</title><source>Royal Society Of Chemistry Journals 2008-</source><creator>Prakash Rao, H. Surya ; Desai, Avinash</creator><creatorcontrib>Prakash Rao, H. Surya ; Desai, Avinash</creatorcontrib><description>The synthesis and evaluation of the photochromic properties of 3-acylcoumarins are very important as they exhibit selective sensing properties. We found that InCl
3
efficiently catalyzes the condensation of 2-hydroxybenzaldehydes and β-keto esters to provide near quantitative yields of 3-acylcoumarins. The 3-(phenylsulfanyl/phenylsulfinyl/phenylsufonyl)propanoyl coumarins with an electron-donating NMe
2
group at the C7 position were prepared to evaluate the influence of sulfur on the emission and acetate ion sensing properties. Our studies revealed that 7-(diethylamino)-3-(3-(phenylsulfanyl/phenylsulfinyl/phenylsufonyl)propanoyl)-2
H
-chromen-2-one exhibits excellent fluorescence emission in hexane and ethyl acetate (
Φ
≈ 80%). The 3-acylcoumarin with sulfone in the C3-acyl side-chain detects acetate anions selectively and this property can be conveniently followed by fluorescence emission spectroscopy.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/C4RA09228G</identifier><language>eng</language><subject>Acetates ; Detection ; Emission analysis ; Esters ; Fluorescence ; Hexanes ; Sulfur ; Synthesis</subject><ispartof>RSC advances, 2014-01, Vol.4 (109), p.63642-63649</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c264t-6881fbddac9942c8b576b04f5ec40ac63f5b6568dbce2ac9975976e296664eab3</citedby><cites>FETCH-LOGICAL-c264t-6881fbddac9942c8b576b04f5ec40ac63f5b6568dbce2ac9975976e296664eab3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Prakash Rao, H. Surya</creatorcontrib><creatorcontrib>Desai, Avinash</creatorcontrib><title>The indium( iii ) chloride catalyzed synthesis of sulfur incorporated 3-acylcoumarins; their photochromic and acetate sensing properties</title><title>RSC advances</title><description>The synthesis and evaluation of the photochromic properties of 3-acylcoumarins are very important as they exhibit selective sensing properties. We found that InCl
3
efficiently catalyzes the condensation of 2-hydroxybenzaldehydes and β-keto esters to provide near quantitative yields of 3-acylcoumarins. The 3-(phenylsulfanyl/phenylsulfinyl/phenylsufonyl)propanoyl coumarins with an electron-donating NMe
2
group at the C7 position were prepared to evaluate the influence of sulfur on the emission and acetate ion sensing properties. Our studies revealed that 7-(diethylamino)-3-(3-(phenylsulfanyl/phenylsulfinyl/phenylsufonyl)propanoyl)-2
H
-chromen-2-one exhibits excellent fluorescence emission in hexane and ethyl acetate (
Φ
≈ 80%). The 3-acylcoumarin with sulfone in the C3-acyl side-chain detects acetate anions selectively and this property can be conveniently followed by fluorescence emission spectroscopy.</description><subject>Acetates</subject><subject>Detection</subject><subject>Emission analysis</subject><subject>Esters</subject><subject>Fluorescence</subject><subject>Hexanes</subject><subject>Sulfur</subject><subject>Synthesis</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpNkEFLxDAQhYMouKx78RfkuArVJG3TFk_LoquwIMh6Lul0aiNtU5P0UH-BP9ssCjqXmcP33mMeIZec3XAWF7fb5GXDCiHy3QlZCJbISDBZnP67z8nKuXcWRqZcSL4gX4cWqR5qPfVrqrWmVxTazlhdIwXlVTd_Yk3dPPgWnXbUNNRNXTPZIAJjR2OVD0AcKZg7MFOvrB7cHQ24tnRsjTfQWtNroGqoqQL0QUAdDk4Pb3S0ZkTrNboLctaozuHqdy_J68P9YfsY7Z93T9vNPgIhEx_JPOdNVdcKiiIRkFdpJiuWNClCwhTIuEkrmcq8rgDFEcrSIpMoCillgqqKl2T94xuiPyZ0vuy1A-w6NaCZXMmzmLEkkxkP6PUPCtY4Z7EpR6vDg3PJWXlsvPxrPP4GPVN2FA</recordid><startdate>20140101</startdate><enddate>20140101</enddate><creator>Prakash Rao, H. Surya</creator><creator>Desai, Avinash</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140101</creationdate><title>The indium( iii ) chloride catalyzed synthesis of sulfur incorporated 3-acylcoumarins; their photochromic and acetate sensing properties</title><author>Prakash Rao, H. Surya ; Desai, Avinash</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c264t-6881fbddac9942c8b576b04f5ec40ac63f5b6568dbce2ac9975976e296664eab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Acetates</topic><topic>Detection</topic><topic>Emission analysis</topic><topic>Esters</topic><topic>Fluorescence</topic><topic>Hexanes</topic><topic>Sulfur</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Prakash Rao, H. Surya</creatorcontrib><creatorcontrib>Desai, Avinash</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Prakash Rao, H. Surya</au><au>Desai, Avinash</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The indium( iii ) chloride catalyzed synthesis of sulfur incorporated 3-acylcoumarins; their photochromic and acetate sensing properties</atitle><jtitle>RSC advances</jtitle><date>2014-01-01</date><risdate>2014</risdate><volume>4</volume><issue>109</issue><spage>63642</spage><epage>63649</epage><pages>63642-63649</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The synthesis and evaluation of the photochromic properties of 3-acylcoumarins are very important as they exhibit selective sensing properties. We found that InCl
3
efficiently catalyzes the condensation of 2-hydroxybenzaldehydes and β-keto esters to provide near quantitative yields of 3-acylcoumarins. The 3-(phenylsulfanyl/phenylsulfinyl/phenylsufonyl)propanoyl coumarins with an electron-donating NMe
2
group at the C7 position were prepared to evaluate the influence of sulfur on the emission and acetate ion sensing properties. Our studies revealed that 7-(diethylamino)-3-(3-(phenylsulfanyl/phenylsulfinyl/phenylsufonyl)propanoyl)-2
H
-chromen-2-one exhibits excellent fluorescence emission in hexane and ethyl acetate (
Φ
≈ 80%). The 3-acylcoumarin with sulfone in the C3-acyl side-chain detects acetate anions selectively and this property can be conveniently followed by fluorescence emission spectroscopy.</abstract><doi>10.1039/C4RA09228G</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2046-2069 |
| ispartof | RSC advances, 2014-01, Vol.4 (109), p.63642-63649 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1730047671 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Acetates Detection Emission analysis Esters Fluorescence Hexanes Sulfur Synthesis |
| title | The indium( iii ) chloride catalyzed synthesis of sulfur incorporated 3-acylcoumarins; their photochromic and acetate sensing properties |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-13T09%3A48%3A01IST&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=The%20indium(%20iii%20)%20chloride%20catalyzed%20synthesis%20of%20sulfur%20incorporated%203-acylcoumarins;%20their%20photochromic%20and%20acetate%20sensing%20properties&rft.jtitle=RSC%20advances&rft.au=Prakash%20Rao,%20H.%20Surya&rft.date=2014-01-01&rft.volume=4&rft.issue=109&rft.spage=63642&rft.epage=63649&rft.pages=63642-63649&rft.issn=2046-2069&rft.eissn=2046-2069&rft_id=info:doi/10.1039/C4RA09228G&rft_dat=%3Cproquest_cross%3E1730047671%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=1730047671&rft_id=info:pmid/&rfr_iscdi=true |