Thermal and magnetic dual-responsive l-proline nanohybrids for aqueous asymmetric aldol reaction
Thermal and magnetic dual-responsive l-proline nanohybrids (l-Pro-based-TMNHs) were prepared by grafting thermal-responsive thiol-terminated P(NIPAM-co-l-ProlA)-b-POEGA-SH (PNLPO-SH) to vinyl-functionalized Fe3O4@SiO2-MPS through the thiol-ene click chemistry. The catalytic activity, selectivity and...
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| Veröffentlicht in: | Reactive & functional polymers 2020-04, Vol.149, p.104508, Article 104508 |
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| creator | Wang, Qinya Tang, Yu Wu, Lexuan Xu, Weiwei Shen, Yinghua Shi, Lijuan Dai, Sheng |
| description | Thermal and magnetic dual-responsive l-proline nanohybrids (l-Pro-based-TMNHs) were prepared by grafting thermal-responsive thiol-terminated P(NIPAM-co-l-ProlA)-b-POEGA-SH (PNLPO-SH) to vinyl-functionalized Fe3O4@SiO2-MPS through the thiol-ene click chemistry. The catalytic activity, selectivity and recyclability of l-Pro-based-TMNHs were evaluated in a model asymmetric aldol reaction of cyclohexanone and 4-nitrobenzaldehyde in water. Thermal responsiveness of the l-Pro-based-TMNHs induced self-assembly to produce a hydrophobic microenvironment in aqueous medium for catalyzing asymmetric aldol reaction. The catalytic performance can be tuned by the molar ratio of PNLPO-SH to Fe3O4@SiO2-MPS, and l-Pro-based-TMNHs-2 with a ratio of 1:6 exhibited best catalytic activity and selectivity. At 50 °C and 5 mol% catalyst loading, 94% conv., 81/19 anti/syn and 95% ee were obtained. On the other hand, magnetic responsiveness of the l-Pro-based-TMNHs facilitates catalyst separation and reuse in the presence of an external magnetic field, and these results indicated no loss of both catalytic activity and selectivity associated with the course of recycling. |
| doi_str_mv | 10.1016/j.reactfunctpolym.2020.104508 |
| format | Article |
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The catalytic activity, selectivity and recyclability of l-Pro-based-TMNHs were evaluated in a model asymmetric aldol reaction of cyclohexanone and 4-nitrobenzaldehyde in water. Thermal responsiveness of the l-Pro-based-TMNHs induced self-assembly to produce a hydrophobic microenvironment in aqueous medium for catalyzing asymmetric aldol reaction. The catalytic performance can be tuned by the molar ratio of PNLPO-SH to Fe3O4@SiO2-MPS, and l-Pro-based-TMNHs-2 with a ratio of 1:6 exhibited best catalytic activity and selectivity. At 50 °C and 5 mol% catalyst loading, 94% conv., 81/19 anti/syn and 95% ee were obtained. On the other hand, magnetic responsiveness of the l-Pro-based-TMNHs facilitates catalyst separation and reuse in the presence of an external magnetic field, and these results indicated no loss of both catalytic activity and selectivity associated with the course of recycling.</description><identifier>ISSN: 1381-5148</identifier><identifier>EISSN: 1873-166X</identifier><identifier>DOI: 10.1016/j.reactfunctpolym.2020.104508</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Aldehydes ; Aqueous solutions ; Asymmetric aldol reaction ; Asymmetry ; Catalysis ; Catalysts ; Catalytic activity ; Chemical activity ; Chemical synthesis ; Cyclohexanone ; Fe3O4 ; Iron oxides ; l-Proline ; Magnetic fields ; Magnetism ; Nanoparticles ; Proline ; Recyclability ; Selectivity ; Self-assembly ; Silicon dioxide ; Thermal-responsive polymer</subject><ispartof>Reactive & functional polymers, 2020-04, Vol.149, p.104508, Article 104508</ispartof><rights>2020 Elsevier B.V.</rights><rights>Copyright Elsevier BV Apr 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c361t-f2457b634368c1ce94627c46796b3aeea7b5b107165c3b0c4a76eec3ee69cd783</citedby><cites>FETCH-LOGICAL-c361t-f2457b634368c1ce94627c46796b3aeea7b5b107165c3b0c4a76eec3ee69cd783</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.reactfunctpolym.2020.104508$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Wang, Qinya</creatorcontrib><creatorcontrib>Tang, Yu</creatorcontrib><creatorcontrib>Wu, Lexuan</creatorcontrib><creatorcontrib>Xu, Weiwei</creatorcontrib><creatorcontrib>Shen, Yinghua</creatorcontrib><creatorcontrib>Shi, Lijuan</creatorcontrib><creatorcontrib>Dai, Sheng</creatorcontrib><title>Thermal and magnetic dual-responsive l-proline nanohybrids for aqueous asymmetric aldol reaction</title><title>Reactive & functional polymers</title><description>Thermal and magnetic dual-responsive l-proline nanohybrids (l-Pro-based-TMNHs) were prepared by grafting thermal-responsive thiol-terminated P(NIPAM-co-l-ProlA)-b-POEGA-SH (PNLPO-SH) to vinyl-functionalized Fe3O4@SiO2-MPS through the thiol-ene click chemistry. The catalytic activity, selectivity and recyclability of l-Pro-based-TMNHs were evaluated in a model asymmetric aldol reaction of cyclohexanone and 4-nitrobenzaldehyde in water. Thermal responsiveness of the l-Pro-based-TMNHs induced self-assembly to produce a hydrophobic microenvironment in aqueous medium for catalyzing asymmetric aldol reaction. The catalytic performance can be tuned by the molar ratio of PNLPO-SH to Fe3O4@SiO2-MPS, and l-Pro-based-TMNHs-2 with a ratio of 1:6 exhibited best catalytic activity and selectivity. At 50 °C and 5 mol% catalyst loading, 94% conv., 81/19 anti/syn and 95% ee were obtained. On the other hand, magnetic responsiveness of the l-Pro-based-TMNHs facilitates catalyst separation and reuse in the presence of an external magnetic field, and these results indicated no loss of both catalytic activity and selectivity associated with the course of recycling.</description><subject>Aldehydes</subject><subject>Aqueous solutions</subject><subject>Asymmetric aldol reaction</subject><subject>Asymmetry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Catalytic activity</subject><subject>Chemical activity</subject><subject>Chemical synthesis</subject><subject>Cyclohexanone</subject><subject>Fe3O4</subject><subject>Iron oxides</subject><subject>l-Proline</subject><subject>Magnetic fields</subject><subject>Magnetism</subject><subject>Nanoparticles</subject><subject>Proline</subject><subject>Recyclability</subject><subject>Selectivity</subject><subject>Self-assembly</subject><subject>Silicon dioxide</subject><subject>Thermal-responsive polymer</subject><issn>1381-5148</issn><issn>1873-166X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqNUE1LxDAQLaLguvofAuKxa9KkSXvwIIuuguBlBW8xTaduSpusSbvQf2_WevLkaQbex7x5SXJD8Ipgwm_blQelh2a0eti7bupXGc6OGMtxcZIsSCFoSjh_P407LUiaE1acJxchtBgTEZFF8rHdge9Vh5StUa8-LQxGo3pUXeoh7J0N5gCoS_fedcYCssq63VR5UwfUOI_U1whuDEiFqe9h8FGsutp16CeacfYyOWtUF-Dqdy6Tt8eH7fopfXndPK_vX1JNORnSJmO5qDhllBeaaCgZz4RmXJS8ogpAiSqvCI6hc00rrJkSHEBTAF7qWhR0mVzPvjFpzBQG2brR23hSZoyRXJS4yCPrbmZp70Lw0Mi9N73ykyRYHkuVrfxTqjyWKudSo34z6yG-cjDgZdAGrIbaeNCDrJ35p9M35-aMIQ</recordid><startdate>202004</startdate><enddate>202004</enddate><creator>Wang, Qinya</creator><creator>Tang, Yu</creator><creator>Wu, Lexuan</creator><creator>Xu, Weiwei</creator><creator>Shen, Yinghua</creator><creator>Shi, Lijuan</creator><creator>Dai, Sheng</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>202004</creationdate><title>Thermal and magnetic dual-responsive l-proline nanohybrids for aqueous asymmetric aldol reaction</title><author>Wang, Qinya ; Tang, Yu ; Wu, Lexuan ; Xu, Weiwei ; Shen, Yinghua ; Shi, Lijuan ; Dai, Sheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c361t-f2457b634368c1ce94627c46796b3aeea7b5b107165c3b0c4a76eec3ee69cd783</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aldehydes</topic><topic>Aqueous solutions</topic><topic>Asymmetric aldol reaction</topic><topic>Asymmetry</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Catalytic activity</topic><topic>Chemical activity</topic><topic>Chemical synthesis</topic><topic>Cyclohexanone</topic><topic>Fe3O4</topic><topic>Iron oxides</topic><topic>l-Proline</topic><topic>Magnetic fields</topic><topic>Magnetism</topic><topic>Nanoparticles</topic><topic>Proline</topic><topic>Recyclability</topic><topic>Selectivity</topic><topic>Self-assembly</topic><topic>Silicon dioxide</topic><topic>Thermal-responsive polymer</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Qinya</creatorcontrib><creatorcontrib>Tang, Yu</creatorcontrib><creatorcontrib>Wu, Lexuan</creatorcontrib><creatorcontrib>Xu, Weiwei</creatorcontrib><creatorcontrib>Shen, Yinghua</creatorcontrib><creatorcontrib>Shi, Lijuan</creatorcontrib><creatorcontrib>Dai, Sheng</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Reactive & functional polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Qinya</au><au>Tang, Yu</au><au>Wu, Lexuan</au><au>Xu, Weiwei</au><au>Shen, Yinghua</au><au>Shi, Lijuan</au><au>Dai, Sheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thermal and magnetic dual-responsive l-proline nanohybrids for aqueous asymmetric aldol reaction</atitle><jtitle>Reactive & functional polymers</jtitle><date>2020-04</date><risdate>2020</risdate><volume>149</volume><spage>104508</spage><pages>104508-</pages><artnum>104508</artnum><issn>1381-5148</issn><eissn>1873-166X</eissn><abstract>Thermal and magnetic dual-responsive l-proline nanohybrids (l-Pro-based-TMNHs) were prepared by grafting thermal-responsive thiol-terminated P(NIPAM-co-l-ProlA)-b-POEGA-SH (PNLPO-SH) to vinyl-functionalized Fe3O4@SiO2-MPS through the thiol-ene click chemistry. The catalytic activity, selectivity and recyclability of l-Pro-based-TMNHs were evaluated in a model asymmetric aldol reaction of cyclohexanone and 4-nitrobenzaldehyde in water. Thermal responsiveness of the l-Pro-based-TMNHs induced self-assembly to produce a hydrophobic microenvironment in aqueous medium for catalyzing asymmetric aldol reaction. The catalytic performance can be tuned by the molar ratio of PNLPO-SH to Fe3O4@SiO2-MPS, and l-Pro-based-TMNHs-2 with a ratio of 1:6 exhibited best catalytic activity and selectivity. At 50 °C and 5 mol% catalyst loading, 94% conv., 81/19 anti/syn and 95% ee were obtained. On the other hand, magnetic responsiveness of the l-Pro-based-TMNHs facilitates catalyst separation and reuse in the presence of an external magnetic field, and these results indicated no loss of both catalytic activity and selectivity associated with the course of recycling.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.reactfunctpolym.2020.104508</doi></addata></record> |
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| subjects | Aldehydes Aqueous solutions Asymmetric aldol reaction Asymmetry Catalysis Catalysts Catalytic activity Chemical activity Chemical synthesis Cyclohexanone Fe3O4 Iron oxides l-Proline Magnetic fields Magnetism Nanoparticles Proline Recyclability Selectivity Self-assembly Silicon dioxide Thermal-responsive polymer |
| title | Thermal and magnetic dual-responsive l-proline nanohybrids for aqueous asymmetric aldol reaction |
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