A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition
We have synthesized mesoporous silica (monoliths) with defined surface chemistry by means of a number of addition reactions: (i) coupling of an isocyanate to a surface‐immobilized thiol, (ii) addition of an epoxide to a surface‐immobilized thiol, (iii) cross‐metathesis between two olefins, and (iv)...
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| Veröffentlicht in: | European journal of inorganic chemistry 2016-05, Vol.2016 (13-14), p.2088-2099 |
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| container_title | European journal of inorganic chemistry |
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| creator | Göbel, Ronald Stoltenberg, Marcus Krehl, Stefan Biolley, Christine Rothe, Regina Schmidt, Bernd Hesemann, Peter Taubert, Andreas |
| description | We have synthesized mesoporous silica (monoliths) with defined surface chemistry by means of a number of addition reactions: (i) coupling of an isocyanate to a surface‐immobilized thiol, (ii) addition of an epoxide to a surface‐immobilized thiol, (iii) cross‐metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne‐functionalized silica monolith with an azide. Functionalization of the mesopores was observed, but there are significant differences between individual approaches. Isocyanate and epoxide additions lead to high degrees of functionalization, whereas olefin metathesis and [2+3] cycloaddition are less effective. We further show that the efficiency of the modification is about twice as high in mesoporous silica particles than in macroscopic silica monoliths.
Mesoporous silica monoliths with defined surface chemistry were synthesized by a number of reactions: (i) coupling of an isocyanate to a surface‐immobilized thiol, (ii) addition of an epoxide to a surface‐immobilized thiol, (iii) cross‐metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne‐functionalized silica monolith with an azide. |
| doi_str_mv | 10.1002/ejic.201500638 |
| format | Article |
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Mesoporous silica monoliths with defined surface chemistry were synthesized by a number of reactions: (i) coupling of an isocyanate to a surface‐immobilized thiol, (ii) addition of an epoxide to a surface‐immobilized thiol, (iii) cross‐metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne‐functionalized silica monolith with an azide.</description><identifier>ISSN: 1434-1948</identifier><identifier>EISSN: 1099-0682</identifier><identifier>DOI: 10.1002/ejic.201500638</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkynes ; Click chemistry ; Coupling ; Cycloaddition ; Hybrid materials ; Isocyanates ; Mesoporous materials ; Nucleophilic addition ; Olefins ; Porous materials ; Silica ; Silicon dioxide ; Surface chemistry ; Thiols</subject><ispartof>European journal of inorganic chemistry, 2016-05, Vol.2016 (13-14), p.2088-2099</ispartof><rights>Copyright © 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2338-c1100c4f3a008b935bbd9c7155502491df1a717191a83d3337f83db518bc23ea3</citedby><cites>FETCH-LOGICAL-c2338-c1100c4f3a008b935bbd9c7155502491df1a717191a83d3337f83db518bc23ea3</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%2Fejic.201500638$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejic.201500638$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Göbel, Ronald</creatorcontrib><creatorcontrib>Stoltenberg, Marcus</creatorcontrib><creatorcontrib>Krehl, Stefan</creatorcontrib><creatorcontrib>Biolley, Christine</creatorcontrib><creatorcontrib>Rothe, Regina</creatorcontrib><creatorcontrib>Schmidt, Bernd</creatorcontrib><creatorcontrib>Hesemann, Peter</creatorcontrib><creatorcontrib>Taubert, Andreas</creatorcontrib><title>A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition</title><title>European journal of inorganic chemistry</title><addtitle>Eur. J. Inorg. Chem</addtitle><description>We have synthesized mesoporous silica (monoliths) with defined surface chemistry by means of a number of addition reactions: (i) coupling of an isocyanate to a surface‐immobilized thiol, (ii) addition of an epoxide to a surface‐immobilized thiol, (iii) cross‐metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne‐functionalized silica monolith with an azide. Functionalization of the mesopores was observed, but there are significant differences between individual approaches. Isocyanate and epoxide additions lead to high degrees of functionalization, whereas olefin metathesis and [2+3] cycloaddition are less effective. We further show that the efficiency of the modification is about twice as high in mesoporous silica particles than in macroscopic silica monoliths.
Mesoporous silica monoliths with defined surface chemistry were synthesized by a number of reactions: (i) coupling of an isocyanate to a surface‐immobilized thiol, (ii) addition of an epoxide to a surface‐immobilized thiol, (iii) cross‐metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne‐functionalized silica monolith with an azide.</description><subject>Alkynes</subject><subject>Click chemistry</subject><subject>Coupling</subject><subject>Cycloaddition</subject><subject>Hybrid materials</subject><subject>Isocyanates</subject><subject>Mesoporous materials</subject><subject>Nucleophilic addition</subject><subject>Olefins</subject><subject>Porous materials</subject><subject>Silica</subject><subject>Silicon dioxide</subject><subject>Surface chemistry</subject><subject>Thiols</subject><issn>1434-1948</issn><issn>1099-0682</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkcFu1DAURSMEEqWwZW2JDYtm8Ivj2GY3GpVpUdupVFCXlmM7jAc3Dnai6fwK_8BP8GV4NFVVdcPGz3o699pXtyjeA54BxtUnu3F6VmGgGDeEvyiOAAtR4oZXL_O9JnUJouavizcpbTDGBJPmqPg9R5fBTF5FNB-GGJReozFsVTQJXdoU_v4ZQgxTQjfOO60y3AfvxnVC23yiVfyh-rz3frf3cZ2zBl2HaNFt3qXP6GrS3oZhvVejuTFudKE_QStvO9fnF0Y1rm1y6QSp3qDFTvugHqi3xatO-WTfPczj4vuX02-Ls_JitTxfzC9KXRHCSw05va47ojDmrSC0bY3QDCiluKoFmA4UAwYCFCeGEMK6PFsKvM0GVpHj4uPBN8f_Ndk0yjuXtPVe9TYnl8ChwRVlHGf0wzN0E6bY599JYJxlitAmU7MDpWNIKdpODtHdqbiTgOW-KrmvSj5WlQXiINg6b3f_oeXp1_PFU2150Lo02vtHrYo_ZcMIo_L2aikbwZc3FK6lIP8AT9Gojg</recordid><startdate>201605</startdate><enddate>201605</enddate><creator>Göbel, Ronald</creator><creator>Stoltenberg, Marcus</creator><creator>Krehl, Stefan</creator><creator>Biolley, Christine</creator><creator>Rothe, Regina</creator><creator>Schmidt, Bernd</creator><creator>Hesemann, Peter</creator><creator>Taubert, Andreas</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>201605</creationdate><title>A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition</title><author>Göbel, Ronald ; Stoltenberg, Marcus ; Krehl, Stefan ; Biolley, Christine ; Rothe, Regina ; Schmidt, Bernd ; Hesemann, Peter ; Taubert, Andreas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2338-c1100c4f3a008b935bbd9c7155502491df1a717191a83d3337f83db518bc23ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Alkynes</topic><topic>Click chemistry</topic><topic>Coupling</topic><topic>Cycloaddition</topic><topic>Hybrid materials</topic><topic>Isocyanates</topic><topic>Mesoporous materials</topic><topic>Nucleophilic addition</topic><topic>Olefins</topic><topic>Porous materials</topic><topic>Silica</topic><topic>Silicon dioxide</topic><topic>Surface chemistry</topic><topic>Thiols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Göbel, Ronald</creatorcontrib><creatorcontrib>Stoltenberg, Marcus</creatorcontrib><creatorcontrib>Krehl, Stefan</creatorcontrib><creatorcontrib>Biolley, Christine</creatorcontrib><creatorcontrib>Rothe, Regina</creatorcontrib><creatorcontrib>Schmidt, Bernd</creatorcontrib><creatorcontrib>Hesemann, Peter</creatorcontrib><creatorcontrib>Taubert, Andreas</creatorcontrib><collection>Istex</collection><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>European journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Göbel, Ronald</au><au>Stoltenberg, Marcus</au><au>Krehl, Stefan</au><au>Biolley, Christine</au><au>Rothe, Regina</au><au>Schmidt, Bernd</au><au>Hesemann, Peter</au><au>Taubert, Andreas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition</atitle><jtitle>European journal of inorganic chemistry</jtitle><addtitle>Eur. J. Inorg. Chem</addtitle><date>2016-05</date><risdate>2016</risdate><volume>2016</volume><issue>13-14</issue><spage>2088</spage><epage>2099</epage><pages>2088-2099</pages><issn>1434-1948</issn><eissn>1099-0682</eissn><abstract>We have synthesized mesoporous silica (monoliths) with defined surface chemistry by means of a number of addition reactions: (i) coupling of an isocyanate to a surface‐immobilized thiol, (ii) addition of an epoxide to a surface‐immobilized thiol, (iii) cross‐metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne‐functionalized silica monolith with an azide. Functionalization of the mesopores was observed, but there are significant differences between individual approaches. Isocyanate and epoxide additions lead to high degrees of functionalization, whereas olefin metathesis and [2+3] cycloaddition are less effective. We further show that the efficiency of the modification is about twice as high in mesoporous silica particles than in macroscopic silica monoliths.
Mesoporous silica monoliths with defined surface chemistry were synthesized by a number of reactions: (i) coupling of an isocyanate to a surface‐immobilized thiol, (ii) addition of an epoxide to a surface‐immobilized thiol, (iii) cross‐metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne‐functionalized silica monolith with an azide.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejic.201500638</doi><tpages>12</tpages></addata></record> |
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| issn | 1434-1948 1099-0682 |
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| source | Wiley-Blackwell Journals |
| subjects | Alkynes Click chemistry Coupling Cycloaddition Hybrid materials Isocyanates Mesoporous materials Nucleophilic addition Olefins Porous materials Silica Silicon dioxide Surface chemistry Thiols |
| title | A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition |
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