Easy Separation of Δ and Λ Isomers of Highly Luminescent [IrIII]-Cyclometalated Complexes Based on Chiral Phenol-Oxazoline Ancillary Ligands
A new class of neutral cyclometalated iridium(III) complexes with enantiomerically pure C1‐symmetric phenol‐oxazolines (3 a,b) have been synthetized in high yields and fully characterized. Resolution of the corresponding ΔR and ΛR or ΔS and ΛS isomers was easily achieved by conventional flash chroma...
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| Veröffentlicht in: | Chemistry : a European journal 2012-07, Vol.18 (28), p.8765-8773 |
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| container_title | Chemistry : a European journal |
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| creator | Marchi, Enrico Sinisi, Riccardo Bergamini, Giacomo Tragni, Michele Monari, Magda Bandini, Marco Ceroni, Paola |
| description | A new class of neutral cyclometalated iridium(III) complexes with enantiomerically pure C1‐symmetric phenol‐oxazolines (3 a,b) have been synthetized in high yields and fully characterized. Resolution of the corresponding ΔR and ΛR or ΔS and ΛS isomers was easily achieved by conventional flash chromatography. The corresponding Δ and Λ helicities have been confirmed by CD spectroscopy and X‐ray crystallography. Regarding the absorption and luminescence properties with unpolarized light, no significant difference between Δ and Λ isomers has been observed. A strong blue luminescence is observed for deaerated solutions of complexes 5 a and 5 b in CH3CN.
Phox and hounds: Δ and Λ isomers of IrIII complexes based on 2‐phenyl‐pyridyl (ppy) cyclometalating ligands and chiral phenol‐oxazoline ancillary ligands (see figure) are readily available through simple separation on an achiral stationary phase. Blue luminescence, combined with an excellent emission quantum yield (Φem=0.80), is recorded for complexes with F2ppy ligands. |
| doi_str_mv | 10.1002/chem.201200709 |
| format | Article |
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Phox and hounds: Δ and Λ isomers of IrIII complexes based on 2‐phenyl‐pyridyl (ppy) cyclometalating ligands and chiral phenol‐oxazoline ancillary ligands (see figure) are readily available through simple separation on an achiral stationary phase. Blue luminescence, combined with an excellent emission quantum yield (Φem=0.80), is recorded for complexes with F2ppy ligands.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201200709</identifier><identifier>PMID: 22689328</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Absorption ; chiral ligands ; circular dichroism ; Emission ; Helicity ; iridium ; Isomers ; Ligands ; Luminescence ; phosphorescence ; Separation ; X-rays</subject><ispartof>Chemistry : a European journal, 2012-07, Vol.18 (28), p.8765-8773</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4569-b0089dd4d2b65047abf1272337f03b1d34f96b04e461c2c5491f8249751915603</citedby><cites>FETCH-LOGICAL-c4569-b0089dd4d2b65047abf1272337f03b1d34f96b04e461c2c5491f8249751915603</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201200709$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201200709$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22689328$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Marchi, Enrico</creatorcontrib><creatorcontrib>Sinisi, Riccardo</creatorcontrib><creatorcontrib>Bergamini, Giacomo</creatorcontrib><creatorcontrib>Tragni, Michele</creatorcontrib><creatorcontrib>Monari, Magda</creatorcontrib><creatorcontrib>Bandini, Marco</creatorcontrib><creatorcontrib>Ceroni, Paola</creatorcontrib><title>Easy Separation of Δ and Λ Isomers of Highly Luminescent [IrIII]-Cyclometalated Complexes Based on Chiral Phenol-Oxazoline Ancillary Ligands</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A new class of neutral cyclometalated iridium(III) complexes with enantiomerically pure C1‐symmetric phenol‐oxazolines (3 a,b) have been synthetized in high yields and fully characterized. Resolution of the corresponding ΔR and ΛR or ΔS and ΛS isomers was easily achieved by conventional flash chromatography. The corresponding Δ and Λ helicities have been confirmed by CD spectroscopy and X‐ray crystallography. Regarding the absorption and luminescence properties with unpolarized light, no significant difference between Δ and Λ isomers has been observed. A strong blue luminescence is observed for deaerated solutions of complexes 5 a and 5 b in CH3CN.
Phox and hounds: Δ and Λ isomers of IrIII complexes based on 2‐phenyl‐pyridyl (ppy) cyclometalating ligands and chiral phenol‐oxazoline ancillary ligands (see figure) are readily available through simple separation on an achiral stationary phase. Blue luminescence, combined with an excellent emission quantum yield (Φem=0.80), is recorded for complexes with F2ppy ligands.</description><subject>Absorption</subject><subject>chiral ligands</subject><subject>circular dichroism</subject><subject>Emission</subject><subject>Helicity</subject><subject>iridium</subject><subject>Isomers</subject><subject>Ligands</subject><subject>Luminescence</subject><subject>phosphorescence</subject><subject>Separation</subject><subject>X-rays</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkU9v0zAYhy0EYmVw5Yh85JLy2k7s-Diibo3oGOJPd0DIchJnNThJsVPR8iE4ceM77TPhqqPitpNl6_k9fl_9EHpOYEoA6Kt6ZbopBUIBBMgHaEIyShImePYQTUCmIuEZkyfoSQhfAUByxh6jE0p5LhnNJ-jXTIcd_mDW2uvRDj0eWnz7G-u-wbd_cBmGzviwf5zbm5Xb4cWms70JtelH_Ln0ZVl-SYpd7SI3aqdH0-Bi6NbObE3Ar3WI9ygtVtZrh9-tTD-45Gqrfw4uavBZX1vntI9eexP_DE_Ro1a7YJ7dnafo0_nsYzFPFlcXZXG2SOo04zKpAHLZNGlDK55BKnTVEiooY6IFVpGGpa3kFaQm5aSmdZZK0uY0lSIjkmQc2Cl6efCu_fB9Y8KoOhuXirP0ZtgERXKAiAtO7keBsoztpRGdHtDaDyF406q1t11cL0JqX5fa16WOdcXAizv3pupMc8T_9RMBeQB-WGd29-hUMZ9d_i9PDlkbRrM9ZrX_prhgIlPXby_Ucvnmvbi-XKpz9hepoLE7</recordid><startdate>20120709</startdate><enddate>20120709</enddate><creator>Marchi, Enrico</creator><creator>Sinisi, Riccardo</creator><creator>Bergamini, Giacomo</creator><creator>Tragni, Michele</creator><creator>Monari, Magda</creator><creator>Bandini, Marco</creator><creator>Ceroni, Paola</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20120709</creationdate><title>Easy Separation of Δ and Λ Isomers of Highly Luminescent [IrIII]-Cyclometalated Complexes Based on Chiral Phenol-Oxazoline Ancillary Ligands</title><author>Marchi, Enrico ; Sinisi, Riccardo ; Bergamini, Giacomo ; Tragni, Michele ; Monari, Magda ; Bandini, Marco ; Ceroni, Paola</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4569-b0089dd4d2b65047abf1272337f03b1d34f96b04e461c2c5491f8249751915603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Absorption</topic><topic>chiral ligands</topic><topic>circular dichroism</topic><topic>Emission</topic><topic>Helicity</topic><topic>iridium</topic><topic>Isomers</topic><topic>Ligands</topic><topic>Luminescence</topic><topic>phosphorescence</topic><topic>Separation</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Marchi, Enrico</creatorcontrib><creatorcontrib>Sinisi, Riccardo</creatorcontrib><creatorcontrib>Bergamini, Giacomo</creatorcontrib><creatorcontrib>Tragni, Michele</creatorcontrib><creatorcontrib>Monari, Magda</creatorcontrib><creatorcontrib>Bandini, Marco</creatorcontrib><creatorcontrib>Ceroni, Paola</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Marchi, Enrico</au><au>Sinisi, Riccardo</au><au>Bergamini, Giacomo</au><au>Tragni, Michele</au><au>Monari, Magda</au><au>Bandini, Marco</au><au>Ceroni, Paola</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Easy Separation of Δ and Λ Isomers of Highly Luminescent [IrIII]-Cyclometalated Complexes Based on Chiral Phenol-Oxazoline Ancillary Ligands</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2012-07-09</date><risdate>2012</risdate><volume>18</volume><issue>28</issue><spage>8765</spage><epage>8773</epage><pages>8765-8773</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A new class of neutral cyclometalated iridium(III) complexes with enantiomerically pure C1‐symmetric phenol‐oxazolines (3 a,b) have been synthetized in high yields and fully characterized. Resolution of the corresponding ΔR and ΛR or ΔS and ΛS isomers was easily achieved by conventional flash chromatography. The corresponding Δ and Λ helicities have been confirmed by CD spectroscopy and X‐ray crystallography. Regarding the absorption and luminescence properties with unpolarized light, no significant difference between Δ and Λ isomers has been observed. A strong blue luminescence is observed for deaerated solutions of complexes 5 a and 5 b in CH3CN.
Phox and hounds: Δ and Λ isomers of IrIII complexes based on 2‐phenyl‐pyridyl (ppy) cyclometalating ligands and chiral phenol‐oxazoline ancillary ligands (see figure) are readily available through simple separation on an achiral stationary phase. Blue luminescence, combined with an excellent emission quantum yield (Φem=0.80), is recorded for complexes with F2ppy ligands.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>22689328</pmid><doi>10.1002/chem.201200709</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Absorption chiral ligands circular dichroism Emission Helicity iridium Isomers Ligands Luminescence phosphorescence Separation X-rays |
| title | Easy Separation of Δ and Λ Isomers of Highly Luminescent [IrIII]-Cyclometalated Complexes Based on Chiral Phenol-Oxazoline Ancillary Ligands |
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