Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water
We have designed and synthesized two amphiphilic calix[6]arene derivatives, CA8 and CA18, that combine the potential to act as wheel components for pseudorotaxane structures with the self-assembly features typical of surfactant molecules in aqueous solution. Their endo-cavity recognition and selfagg...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2013-09, Vol.11 (35), p.5944-5953 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Bussolati, Rocco Carrieri, Pasquale Secchi, Andrea Arduini, Arturo Credi, Alberto Semeraro, Monica Venturi, Margherita Silvi, Serena Velluto, Diana Zappacosta, Romina Fontana, Antonella |
| description | We have designed and synthesized two amphiphilic calix[6]arene derivatives, CA8 and CA18, that combine the potential to act as wheel components for pseudorotaxane structures with the self-assembly features typical of surfactant molecules in aqueous solution. Their endo-cavity recognition and selfaggregation properties were compared with those of a non-amphiphilic analogue, C8. TEM, DLS, and fluorescence experiments show that in water the amphiphilic calixarenes form vesicle- and micelle-like aggregates. The size, nature and properties of such aggregates depend on the length of the alkyl chain anchored at the lower rim of the calix[6]arene skeleton, as well as on the inclusion of a molecular guest into the wheel. Specifically, the release of a fluorescent guest entrapped inside the CA8 vesicles is accelerated in the presence of dioctylviologen axles that can pierce the calixarene cavity. |
| doi_str_mv | 10.1039/c3ob40739j |
| format | Article |
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Specifically, the release of a fluorescent guest entrapped inside the CA8 vesicles is accelerated in the presence of dioctylviologen axles that can pierce the calixarene cavity.</description><subject>Calixarenes - chemical synthesis</subject><subject>Calixarenes - chemistry</subject><subject>Micelles</subject><subject>Phenols - chemical synthesis</subject><subject>Phenols - chemistry</subject><subject>Surface-Active Agents - chemical synthesis</subject><subject>Surface-Active Agents - chemistry</subject><subject>Water - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkM1KAzEYRYMotlY3PoBkKcJo_mYyWUpRKxTc6EaRIcl8sSmZmZq0tn17R6oVLty7ONzFQeickmtKuLqxvDOCSK7mB2hIhZQZybk63G9GBugkpTkhVMlCHKMB44pwVpZD9DrxEHW0M291wAmCy3RK0JiwxZ3DulnMfJ_gLe4Bv3kr3nWEFvB6BhAS1m2Nv3wXug9osd4ESNi3eK2XEE_RkdMhwdlvj9DL_d3zeJJNnx4ex7fTzLJSLjPucqFrpsqay5wxUxDHhGC8tkZSJwsmlHOWUiO4M4U2dU6J0kpLI3JpTM5H6HL3u4jd5wrSsmp8shCCbqFbpYoKJjjjOeU9erVDbexSiuCqRfSNjtuKkurHZfXvsocvfn9XpoF6j_7J499YmW_1</recordid><startdate>20130921</startdate><enddate>20130921</enddate><creator>Bussolati, Rocco</creator><creator>Carrieri, Pasquale</creator><creator>Secchi, Andrea</creator><creator>Arduini, Arturo</creator><creator>Credi, Alberto</creator><creator>Semeraro, Monica</creator><creator>Venturi, Margherita</creator><creator>Silvi, Serena</creator><creator>Velluto, Diana</creator><creator>Zappacosta, Romina</creator><creator>Fontana, Antonella</creator><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></search><sort><creationdate>20130921</creationdate><title>Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water</title><author>Bussolati, Rocco ; Carrieri, Pasquale ; Secchi, Andrea ; Arduini, Arturo ; Credi, Alberto ; Semeraro, Monica ; Venturi, Margherita ; Silvi, Serena ; Velluto, Diana ; Zappacosta, Romina ; Fontana, Antonella</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c287t-3f54ad298d37522b60f24423dcb71f76249ffc11b43fb6abd5109a9a7b457bb53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Calixarenes - chemical synthesis</topic><topic>Calixarenes - chemistry</topic><topic>Micelles</topic><topic>Phenols - chemical synthesis</topic><topic>Phenols - chemistry</topic><topic>Surface-Active Agents - chemical synthesis</topic><topic>Surface-Active Agents - chemistry</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bussolati, Rocco</creatorcontrib><creatorcontrib>Carrieri, Pasquale</creatorcontrib><creatorcontrib>Secchi, Andrea</creatorcontrib><creatorcontrib>Arduini, Arturo</creatorcontrib><creatorcontrib>Credi, Alberto</creatorcontrib><creatorcontrib>Semeraro, Monica</creatorcontrib><creatorcontrib>Venturi, Margherita</creatorcontrib><creatorcontrib>Silvi, Serena</creatorcontrib><creatorcontrib>Velluto, Diana</creatorcontrib><creatorcontrib>Zappacosta, Romina</creatorcontrib><creatorcontrib>Fontana, Antonella</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><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bussolati, Rocco</au><au>Carrieri, Pasquale</au><au>Secchi, Andrea</au><au>Arduini, Arturo</au><au>Credi, Alberto</au><au>Semeraro, Monica</au><au>Venturi, Margherita</au><au>Silvi, Serena</au><au>Velluto, Diana</au><au>Zappacosta, Romina</au><au>Fontana, Antonella</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2013-09-21</date><risdate>2013</risdate><volume>11</volume><issue>35</issue><spage>5944</spage><epage>5953</epage><pages>5944-5953</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>We have designed and synthesized two amphiphilic calix[6]arene derivatives, CA8 and CA18, that combine the potential to act as wheel components for pseudorotaxane structures with the self-assembly features typical of surfactant molecules in aqueous solution. 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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Calixarenes - chemical synthesis Calixarenes - chemistry Micelles Phenols - chemical synthesis Phenols - chemistry Surface-Active Agents - chemical synthesis Surface-Active Agents - chemistry Water - chemistry |
| title | Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water |
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