Physisorption of Three Calix[4]arenes on Alkyl-Functionalized Mesoporous Silica for Biomimetic Ligand Development
Calixarene physisorption onto alkyl-functionalized silica support is presented as an alternative to tethering to reduce synthetic complexity. Three versions of calix[4]arene were synthesized with differing upper rim functional groups: aromatic amine, tert-butyl, and unfunctionalized. Calixarene mole...
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| Veröffentlicht in: | Industrial & engineering chemistry research 2013-11, Vol.52 (47), p.16755-16765 |
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| container_title | Industrial & engineering chemistry research |
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| creator | Desch, Rebecca J Daniel, Breanna Frierson, Ashley Miyahara, Leland Turner, Benjamin T Kim, Jungseung Fantini, Jordan L Guliants, Vadim V Thiel, Stephen W Pinto, Neville G |
| description | Calixarene physisorption onto alkyl-functionalized silica support is presented as an alternative to tethering to reduce synthetic complexity. Three versions of calix[4]arene were synthesized with differing upper rim functional groups: aromatic amine, tert-butyl, and unfunctionalized. Calixarene molecules physisorbed throughout the alkyl layer on the silica following a linear isotherm with a maximum observed loading of 300 μmol g–1. Large exothermic adsorption enthalpies (−60 to −260 kJ mol–1), attributed to van der Waals interactions, were measured for the calixarene physisorption using flow microcalorimetry; large negative entropies were calculated (−140 to −780 J mol–1 K–1). Amine-calix[4]arene was physisorbed onto C18-silica (NCS) through solvent evaporation. The myoglobin uptake on NCS (47 μmol g–1) was twice that on C18-silica; additionally, a greater heat of adsorption (−16.9 ± 2.9 kJ mol–1) was observed on NCS than on C18-support (−12.7 ± 2.2 kJ mol–1). |
| doi_str_mv | 10.1021/ie401970z |
| format | Article |
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Three versions of calix[4]arene were synthesized with differing upper rim functional groups: aromatic amine, tert-butyl, and unfunctionalized. Calixarene molecules physisorbed throughout the alkyl layer on the silica following a linear isotherm with a maximum observed loading of 300 μmol g–1. Large exothermic adsorption enthalpies (−60 to −260 kJ mol–1), attributed to van der Waals interactions, were measured for the calixarene physisorption using flow microcalorimetry; large negative entropies were calculated (−140 to −780 J mol–1 K–1). Amine-calix[4]arene was physisorbed onto C18-silica (NCS) through solvent evaporation. The myoglobin uptake on NCS (47 μmol g–1) was twice that on C18-silica; additionally, a greater heat of adsorption (−16.9 ± 2.9 kJ mol–1) was observed on NCS than on C18-support (−12.7 ± 2.2 kJ mol–1).</description><identifier>ISSN: 0888-5885</identifier><identifier>EISSN: 1520-5045</identifier><identifier>DOI: 10.1021/ie401970z</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>Calixarenes ; Entropy ; Evaporation ; Heat of adsorption ; Mathematical analysis ; Myoglobin ; Silicon dioxide ; Solvents</subject><ispartof>Industrial & engineering chemistry research, 2013-11, Vol.52 (47), p.16755-16765</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a358t-1f810a63f665d31d770288ee0c4c5073d49f2de5076c6b13eadfddcfacbc0b1f3</citedby><cites>FETCH-LOGICAL-a358t-1f810a63f665d31d770288ee0c4c5073d49f2de5076c6b13eadfddcfacbc0b1f3</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/ie401970z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ie401970z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27059,27907,27908,56721,56771</link.rule.ids></links><search><creatorcontrib>Desch, Rebecca J</creatorcontrib><creatorcontrib>Daniel, Breanna</creatorcontrib><creatorcontrib>Frierson, Ashley</creatorcontrib><creatorcontrib>Miyahara, Leland</creatorcontrib><creatorcontrib>Turner, Benjamin T</creatorcontrib><creatorcontrib>Kim, Jungseung</creatorcontrib><creatorcontrib>Fantini, Jordan L</creatorcontrib><creatorcontrib>Guliants, Vadim V</creatorcontrib><creatorcontrib>Thiel, Stephen W</creatorcontrib><creatorcontrib>Pinto, Neville G</creatorcontrib><title>Physisorption of Three Calix[4]arenes on Alkyl-Functionalized Mesoporous Silica for Biomimetic Ligand Development</title><title>Industrial & engineering chemistry research</title><addtitle>Ind. Eng. Chem. Res</addtitle><description>Calixarene physisorption onto alkyl-functionalized silica support is presented as an alternative to tethering to reduce synthetic complexity. Three versions of calix[4]arene were synthesized with differing upper rim functional groups: aromatic amine, tert-butyl, and unfunctionalized. Calixarene molecules physisorbed throughout the alkyl layer on the silica following a linear isotherm with a maximum observed loading of 300 μmol g–1. Large exothermic adsorption enthalpies (−60 to −260 kJ mol–1), attributed to van der Waals interactions, were measured for the calixarene physisorption using flow microcalorimetry; large negative entropies were calculated (−140 to −780 J mol–1 K–1). Amine-calix[4]arene was physisorbed onto C18-silica (NCS) through solvent evaporation. The myoglobin uptake on NCS (47 μmol g–1) was twice that on C18-silica; additionally, a greater heat of adsorption (−16.9 ± 2.9 kJ mol–1) was observed on NCS than on C18-support (−12.7 ± 2.2 kJ mol–1).</description><subject>Calixarenes</subject><subject>Entropy</subject><subject>Evaporation</subject><subject>Heat of adsorption</subject><subject>Mathematical analysis</subject><subject>Myoglobin</subject><subject>Silicon dioxide</subject><subject>Solvents</subject><issn>0888-5885</issn><issn>1520-5045</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNpt0EFLwzAUB_AgCs7pwW-Qi6CHatImbXac06kwUXCeREqWvLjMtOmSTtw-vR0TT57eg_-Px-OP0Ckll5Sk9MoCI3RQkM0e6lGekoQTxvdRjwghEi4EP0RHMS4IIZwz1kPL5_k62uhD01pfY2_wdB4A8Eg6-_3G3mWAGiLuoqH7XLtkvKrVVnbxBjR-hOgbH_wq4hfrrJLY-ICvra9sBa1VeGI_ZK3xDXyB800FdXuMDox0EU5-Zx-9jm-no_tk8nT3MBpOEplx0SbUCEpknpk85zqjuihIKgQAUUxxUmSaDUyqoVtzlc9oBlIbrZWRaqbIjJqsj853d5vglyuIbVnZqMA5WUP3b0nzQZrlXBSsoxc7qoKPMYApm2ArGdYlJeW21vKv1s6e7axUsVz4VeiqiP-4H55DeSo</recordid><startdate>20131127</startdate><enddate>20131127</enddate><creator>Desch, Rebecca J</creator><creator>Daniel, Breanna</creator><creator>Frierson, Ashley</creator><creator>Miyahara, Leland</creator><creator>Turner, Benjamin T</creator><creator>Kim, Jungseung</creator><creator>Fantini, Jordan L</creator><creator>Guliants, Vadim V</creator><creator>Thiel, Stephen W</creator><creator>Pinto, Neville G</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20131127</creationdate><title>Physisorption of Three Calix[4]arenes on Alkyl-Functionalized Mesoporous Silica for Biomimetic Ligand Development</title><author>Desch, Rebecca J ; Daniel, Breanna ; Frierson, Ashley ; Miyahara, Leland ; Turner, Benjamin T ; Kim, Jungseung ; Fantini, Jordan L ; Guliants, Vadim V ; Thiel, Stephen W ; Pinto, Neville G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a358t-1f810a63f665d31d770288ee0c4c5073d49f2de5076c6b13eadfddcfacbc0b1f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Calixarenes</topic><topic>Entropy</topic><topic>Evaporation</topic><topic>Heat of adsorption</topic><topic>Mathematical analysis</topic><topic>Myoglobin</topic><topic>Silicon dioxide</topic><topic>Solvents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Desch, Rebecca J</creatorcontrib><creatorcontrib>Daniel, Breanna</creatorcontrib><creatorcontrib>Frierson, Ashley</creatorcontrib><creatorcontrib>Miyahara, Leland</creatorcontrib><creatorcontrib>Turner, Benjamin T</creatorcontrib><creatorcontrib>Kim, Jungseung</creatorcontrib><creatorcontrib>Fantini, Jordan L</creatorcontrib><creatorcontrib>Guliants, Vadim V</creatorcontrib><creatorcontrib>Thiel, Stephen W</creatorcontrib><creatorcontrib>Pinto, Neville G</creatorcontrib><collection>CrossRef</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>Industrial & engineering chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Desch, Rebecca J</au><au>Daniel, Breanna</au><au>Frierson, Ashley</au><au>Miyahara, Leland</au><au>Turner, Benjamin T</au><au>Kim, Jungseung</au><au>Fantini, Jordan L</au><au>Guliants, Vadim V</au><au>Thiel, Stephen W</au><au>Pinto, Neville G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Physisorption of Three Calix[4]arenes on Alkyl-Functionalized Mesoporous Silica for Biomimetic Ligand Development</atitle><jtitle>Industrial & engineering chemistry research</jtitle><addtitle>Ind. Eng. Chem. Res</addtitle><date>2013-11-27</date><risdate>2013</risdate><volume>52</volume><issue>47</issue><spage>16755</spage><epage>16765</epage><pages>16755-16765</pages><issn>0888-5885</issn><eissn>1520-5045</eissn><abstract>Calixarene physisorption onto alkyl-functionalized silica support is presented as an alternative to tethering to reduce synthetic complexity. Three versions of calix[4]arene were synthesized with differing upper rim functional groups: aromatic amine, tert-butyl, and unfunctionalized. Calixarene molecules physisorbed throughout the alkyl layer on the silica following a linear isotherm with a maximum observed loading of 300 μmol g–1. Large exothermic adsorption enthalpies (−60 to −260 kJ mol–1), attributed to van der Waals interactions, were measured for the calixarene physisorption using flow microcalorimetry; large negative entropies were calculated (−140 to −780 J mol–1 K–1). Amine-calix[4]arene was physisorbed onto C18-silica (NCS) through solvent evaporation. The myoglobin uptake on NCS (47 μmol g–1) was twice that on C18-silica; additionally, a greater heat of adsorption (−16.9 ± 2.9 kJ mol–1) was observed on NCS than on C18-support (−12.7 ± 2.2 kJ mol–1).</abstract><pub>American Chemical Society</pub><doi>10.1021/ie401970z</doi><tpages>11</tpages></addata></record> |
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| source | ACS Publications |
| subjects | Calixarenes Entropy Evaporation Heat of adsorption Mathematical analysis Myoglobin Silicon dioxide Solvents |
| title | Physisorption of Three Calix[4]arenes on Alkyl-Functionalized Mesoporous Silica for Biomimetic Ligand Development |
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