Enantiopure Laterally Functionalized Alleno-Acetylenic Macrocycles: Synthesis, Chiroptical Properties, and Self-Assembly in Aqueous Media
A family of shape‐persistent alleno–acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized and characterized in enantiomerically pure form. Their electronic circular dichroism (ECD) spectra feature a strong chiroptical response, which i...
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| Veröffentlicht in: | Chemistry : a European journal 2014-12, Vol.20 (49), p.16070-16073 |
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| creator | Tzirakis, Manolis D. Alberti, Mariza N. Weissman, Haim Rybtchinski, Boris Diederich, François |
| description | A family of shape‐persistent alleno–acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized and characterized in enantiomerically pure form. Their electronic circular dichroism (ECD) spectra feature a strong chiroptical response, which is more than two times higher than for open‐chain tetrameric analogues. A water‐soluble oligo(ethylene glycol)‐appended SPAAM undergoes self‐assembly in aqueous solution. Morphology studies by cryogenic transmission electron microscopy (cryo‐TEM) revealed the formation of aggregates with fibrous fine structures that correspond to tubular, macrocyclic stacks.
Decorating macrocycles! A family of shape‐persistent alleno–acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized in enantiomerically pure form. Their electronic circular dichroism spectra feature a strong chiroptical response, which is not reduced by large achiral peripheral substituents. The first optically active, water‐soluble oligo(ethylene glycol) (OEG)‐appended SPAAMs were prepared and further characterized by cryo‐TEM, revealing the formation of aggregates with fibrous fine structures that correspond to tubular, macrocyclic stacks. |
| doi_str_mv | 10.1002/chem.201404941 |
| format | Article |
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Decorating macrocycles! A family of shape‐persistent alleno–acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized in enantiomerically pure form. Their electronic circular dichroism spectra feature a strong chiroptical response, which is not reduced by large achiral peripheral substituents. The first optically active, water‐soluble oligo(ethylene glycol) (OEG)‐appended SPAAMs were prepared and further characterized by cryo‐TEM, revealing the formation of aggregates with fibrous fine structures that correspond to tubular, macrocyclic stacks.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201404941</identifier><identifier>PMID: 25346432</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>alleno-acetylenes ; Aqueous solutions ; Chemistry ; chiral macrocycles ; Circularity ; Decoration ; Dichroism ; electronic circular dichroism ; Electronics ; Fine structure ; Jewelry ; Macrocyclic compounds ; scanning probe microscopy ; Self assembly ; Spectra</subject><ispartof>Chemistry : a European journal, 2014-12, Vol.20 (49), p.16070-16073</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4811-4a438fe69a2e23b4ca7680497e492b2d08693a094aedda1c03e102c334db41343</citedby><cites>FETCH-LOGICAL-c4811-4a438fe69a2e23b4ca7680497e492b2d08693a094aedda1c03e102c334db41343</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.201404941$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201404941$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25346432$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tzirakis, Manolis D.</creatorcontrib><creatorcontrib>Alberti, Mariza N.</creatorcontrib><creatorcontrib>Weissman, Haim</creatorcontrib><creatorcontrib>Rybtchinski, Boris</creatorcontrib><creatorcontrib>Diederich, François</creatorcontrib><title>Enantiopure Laterally Functionalized Alleno-Acetylenic Macrocycles: Synthesis, Chiroptical Properties, and Self-Assembly in Aqueous Media</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A family of shape‐persistent alleno–acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized and characterized in enantiomerically pure form. Their electronic circular dichroism (ECD) spectra feature a strong chiroptical response, which is more than two times higher than for open‐chain tetrameric analogues. A water‐soluble oligo(ethylene glycol)‐appended SPAAM undergoes self‐assembly in aqueous solution. Morphology studies by cryogenic transmission electron microscopy (cryo‐TEM) revealed the formation of aggregates with fibrous fine structures that correspond to tubular, macrocyclic stacks.
Decorating macrocycles! A family of shape‐persistent alleno–acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized in enantiomerically pure form. Their electronic circular dichroism spectra feature a strong chiroptical response, which is not reduced by large achiral peripheral substituents. The first optically active, water‐soluble oligo(ethylene glycol) (OEG)‐appended SPAAMs were prepared and further characterized by cryo‐TEM, revealing the formation of aggregates with fibrous fine structures that correspond to tubular, macrocyclic stacks.</description><subject>alleno-acetylenes</subject><subject>Aqueous solutions</subject><subject>Chemistry</subject><subject>chiral macrocycles</subject><subject>Circularity</subject><subject>Decoration</subject><subject>Dichroism</subject><subject>electronic circular dichroism</subject><subject>Electronics</subject><subject>Fine structure</subject><subject>Jewelry</subject><subject>Macrocyclic compounds</subject><subject>scanning probe microscopy</subject><subject>Self assembly</subject><subject>Spectra</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkU-P0zAQxS0EYsvClSOKxIUDKf4XO-YWVe0W0cJKXcTRcpyp6sVNunYiCN-Ab41Llwpx2ZNHo99745mH0EuCpwRj-s7uYD-lmHDMFSeP0IQUlORMiuIxmmDFZS4Kpi7QsxhvMcZKMPYUXdCCccEZnaBf89a0vesOQ4BsZXoIxvsxWwytTd3WePcTmqzyHtouryz0Y6qczdbGhs6O1kN8n23Gtt9BdPFtNtu50B16Z43PrlMFoXeQ-qZtsg34bV7FCPs6jXBtVt0N0A0xW0PjzHP0ZGt8hBf37yX6spjfzJb56vPVh1m1yi0vCcm54azcglCGAmU1t0aKMi0vgSta0waXQjGTNjfQNIZYzIBgahnjTc0J4-wSvTn5HkKX5sde71204L1pj5_RRJaCKIkFfhgVVKqCEUIS-vo_9LYbQrrfH0pIydPFEzU9Uel4MQbY6kNwexNGTbA-5qmPeepznknw6t52qPfQnPG_ASZAnYDvzsP4gJ2eLefrf83zk9bFHn6ctSZ800IyWeivn6708vpGbNbyo16w32WAu_M</recordid><startdate>20141201</startdate><enddate>20141201</enddate><creator>Tzirakis, Manolis D.</creator><creator>Alberti, Mariza N.</creator><creator>Weissman, Haim</creator><creator>Rybtchinski, Boris</creator><creator>Diederich, François</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20141201</creationdate><title>Enantiopure Laterally Functionalized Alleno-Acetylenic Macrocycles: Synthesis, Chiroptical Properties, and Self-Assembly in Aqueous Media</title><author>Tzirakis, Manolis D. ; Alberti, Mariza N. ; Weissman, Haim ; Rybtchinski, Boris ; Diederich, François</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4811-4a438fe69a2e23b4ca7680497e492b2d08693a094aedda1c03e102c334db41343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>alleno-acetylenes</topic><topic>Aqueous solutions</topic><topic>Chemistry</topic><topic>chiral macrocycles</topic><topic>Circularity</topic><topic>Decoration</topic><topic>Dichroism</topic><topic>electronic circular dichroism</topic><topic>Electronics</topic><topic>Fine structure</topic><topic>Jewelry</topic><topic>Macrocyclic compounds</topic><topic>scanning probe microscopy</topic><topic>Self assembly</topic><topic>Spectra</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tzirakis, Manolis D.</creatorcontrib><creatorcontrib>Alberti, Mariza N.</creatorcontrib><creatorcontrib>Weissman, Haim</creatorcontrib><creatorcontrib>Rybtchinski, Boris</creatorcontrib><creatorcontrib>Diederich, François</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tzirakis, Manolis D.</au><au>Alberti, Mariza N.</au><au>Weissman, Haim</au><au>Rybtchinski, Boris</au><au>Diederich, François</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantiopure Laterally Functionalized Alleno-Acetylenic Macrocycles: Synthesis, Chiroptical Properties, and Self-Assembly in Aqueous Media</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2014-12-01</date><risdate>2014</risdate><volume>20</volume><issue>49</issue><spage>16070</spage><epage>16073</epage><pages>16070-16073</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A family of shape‐persistent alleno–acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized and characterized in enantiomerically pure form. Their electronic circular dichroism (ECD) spectra feature a strong chiroptical response, which is more than two times higher than for open‐chain tetrameric analogues. A water‐soluble oligo(ethylene glycol)‐appended SPAAM undergoes self‐assembly in aqueous solution. Morphology studies by cryogenic transmission electron microscopy (cryo‐TEM) revealed the formation of aggregates with fibrous fine structures that correspond to tubular, macrocyclic stacks.
Decorating macrocycles! A family of shape‐persistent alleno–acetylenic macrocycles (SPAAMs), peripherally decorated with structurally diverse pendant groups, has been synthesized in enantiomerically pure form. Their electronic circular dichroism spectra feature a strong chiroptical response, which is not reduced by large achiral peripheral substituents. The first optically active, water‐soluble oligo(ethylene glycol) (OEG)‐appended SPAAMs were prepared and further characterized by cryo‐TEM, revealing the formation of aggregates with fibrous fine structures that correspond to tubular, macrocyclic stacks.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25346432</pmid><doi>10.1002/chem.201404941</doi><tpages>4</tpages></addata></record> |
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| subjects | alleno-acetylenes Aqueous solutions Chemistry chiral macrocycles Circularity Decoration Dichroism electronic circular dichroism Electronics Fine structure Jewelry Macrocyclic compounds scanning probe microscopy Self assembly Spectra |
| title | Enantiopure Laterally Functionalized Alleno-Acetylenic Macrocycles: Synthesis, Chiroptical Properties, and Self-Assembly in Aqueous Media |
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