Facile methacrylation of cellulose via alkaline aqueous esterification for thiol–ene click functionalization
•Facile methacrylation of cellulose was realized by alkaline aqueous esterification.•Obtained methacrylated cellulose is feasible for thiol–ene click functionalization.•Our strategy enables thiolated functional groups easily to graft cellulose. In this contribution, alkaline carbonates were used as...
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| Veröffentlicht in: | Materials letters 2019-06, Vol.245, p.18-21 |
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| container_title | Materials letters |
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| creator | Chen, Heng Li, Rui Xie, Jintao Xu, Xiayi Chen, Shaojun |
| description | •Facile methacrylation of cellulose was realized by alkaline aqueous esterification.•Obtained methacrylated cellulose is feasible for thiol–ene click functionalization.•Our strategy enables thiolated functional groups easily to graft cellulose.
In this contribution, alkaline carbonates were used as catalyst to develop an one-pot approach for esterification between cellulose and methacrylate anhydrides in aqueous solution. FTIR, 13C CP/MAS NMR and XRD analysis revealed successful esterification in amorphous domains of cellulose without affecting the cellulose crystal structure. The obtained methacrylated cellulose was amenable to further functionalization via thiol–ene click reactions. After this esterification under alkaline aqueous condition, cellulose can be easily grafted with thiolated motifs including fluorophores and bioactive peptide. Our work demonstrates an easy strategy for cellulose modification and functionalization and will greatly promote the wide-spread applications of cellulose-based materials. |
| doi_str_mv | 10.1016/j.matlet.2019.02.083 |
| format | Article |
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In this contribution, alkaline carbonates were used as catalyst to develop an one-pot approach for esterification between cellulose and methacrylate anhydrides in aqueous solution. FTIR, 13C CP/MAS NMR and XRD analysis revealed successful esterification in amorphous domains of cellulose without affecting the cellulose crystal structure. The obtained methacrylated cellulose was amenable to further functionalization via thiol–ene click reactions. After this esterification under alkaline aqueous condition, cellulose can be easily grafted with thiolated motifs including fluorophores and bioactive peptide. Our work demonstrates an easy strategy for cellulose modification and functionalization and will greatly promote the wide-spread applications of cellulose-based materials.</description><identifier>ISSN: 0167-577X</identifier><identifier>EISSN: 1873-4979</identifier><identifier>DOI: 10.1016/j.matlet.2019.02.083</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Anhydrides ; Aqueous esterification ; Aqueous solutions ; Biomaterials ; Carbon 13 ; Carbonates ; Cellulose ; Cellulose esters ; Chemical compounds ; Crystal structure ; Crystals ; Domains ; Esterification ; Fluorescence ; Functional ; Materials science ; NMR spectroscopy ; Thiol−ene</subject><ispartof>Materials letters, 2019-06, Vol.245, p.18-21</ispartof><rights>2019 Elsevier B.V.</rights><rights>Copyright Elsevier BV Jun 15, 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c334t-9a3b800e4e27742abfbc991cb97eb4f3c55d527a5b13c7764af4021f996158b13</citedby><cites>FETCH-LOGICAL-c334t-9a3b800e4e27742abfbc991cb97eb4f3c55d527a5b13c7764af4021f996158b13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0167577X19303246$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids></links><search><creatorcontrib>Chen, Heng</creatorcontrib><creatorcontrib>Li, Rui</creatorcontrib><creatorcontrib>Xie, Jintao</creatorcontrib><creatorcontrib>Xu, Xiayi</creatorcontrib><creatorcontrib>Chen, Shaojun</creatorcontrib><title>Facile methacrylation of cellulose via alkaline aqueous esterification for thiol–ene click functionalization</title><title>Materials letters</title><description>•Facile methacrylation of cellulose was realized by alkaline aqueous esterification.•Obtained methacrylated cellulose is feasible for thiol–ene click functionalization.•Our strategy enables thiolated functional groups easily to graft cellulose.
In this contribution, alkaline carbonates were used as catalyst to develop an one-pot approach for esterification between cellulose and methacrylate anhydrides in aqueous solution. FTIR, 13C CP/MAS NMR and XRD analysis revealed successful esterification in amorphous domains of cellulose without affecting the cellulose crystal structure. The obtained methacrylated cellulose was amenable to further functionalization via thiol–ene click reactions. After this esterification under alkaline aqueous condition, cellulose can be easily grafted with thiolated motifs including fluorophores and bioactive peptide. Our work demonstrates an easy strategy for cellulose modification and functionalization and will greatly promote the wide-spread applications of cellulose-based materials.</description><subject>Anhydrides</subject><subject>Aqueous esterification</subject><subject>Aqueous solutions</subject><subject>Biomaterials</subject><subject>Carbon 13</subject><subject>Carbonates</subject><subject>Cellulose</subject><subject>Cellulose esters</subject><subject>Chemical compounds</subject><subject>Crystal structure</subject><subject>Crystals</subject><subject>Domains</subject><subject>Esterification</subject><subject>Fluorescence</subject><subject>Functional</subject><subject>Materials science</subject><subject>NMR spectroscopy</subject><subject>Thiol−ene</subject><issn>0167-577X</issn><issn>1873-4979</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kE1KBDEQhYMoOP7cwEXAdbdJOj3pbAQR_0Bwo-AupDMVJjOZjiZpQVfewRt6EjO2a1cFVd97vHoInVBSU0LnZ6t6o7OHXDNCZU1YTbpmB81oJ5qKSyF30axgomqFeN5HBymtCCFcEj5Dw7U2zgPeQF5qE9-9zi4MOFhswPvRhwT4zWms_Vp7NwDWryOEMWFIGaKzzkwCGyLOSxf89-cXFMx4Z9bYjoPZnov045c7QntW-wTHf_MQPV1fPV7eVvcPN3eXF_eVaRqeK6mbviMEODAhONO97Y2U1PRSQM9tY9p20TKh2542Rog515YTRq2Uc9p2ZXmITifflxhK4JTVKoyx5EiKMTrvJONcFopPlIkhpQhWvUS30fFdUaK2zaqVmppV22YVYao0W2TnkwzKB28OokrGwWBg4SKYrBbB_W_wA1hPh0o</recordid><startdate>20190615</startdate><enddate>20190615</enddate><creator>Chen, Heng</creator><creator>Li, Rui</creator><creator>Xie, Jintao</creator><creator>Xu, Xiayi</creator><creator>Chen, Shaojun</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20190615</creationdate><title>Facile methacrylation of cellulose via alkaline aqueous esterification for thiol–ene click functionalization</title><author>Chen, Heng ; Li, Rui ; Xie, Jintao ; Xu, Xiayi ; Chen, Shaojun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c334t-9a3b800e4e27742abfbc991cb97eb4f3c55d527a5b13c7764af4021f996158b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Anhydrides</topic><topic>Aqueous esterification</topic><topic>Aqueous solutions</topic><topic>Biomaterials</topic><topic>Carbon 13</topic><topic>Carbonates</topic><topic>Cellulose</topic><topic>Cellulose esters</topic><topic>Chemical compounds</topic><topic>Crystal structure</topic><topic>Crystals</topic><topic>Domains</topic><topic>Esterification</topic><topic>Fluorescence</topic><topic>Functional</topic><topic>Materials science</topic><topic>NMR spectroscopy</topic><topic>Thiol−ene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Heng</creatorcontrib><creatorcontrib>Li, Rui</creatorcontrib><creatorcontrib>Xie, Jintao</creatorcontrib><creatorcontrib>Xu, Xiayi</creatorcontrib><creatorcontrib>Chen, Shaojun</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Materials letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Heng</au><au>Li, Rui</au><au>Xie, Jintao</au><au>Xu, Xiayi</au><au>Chen, Shaojun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile methacrylation of cellulose via alkaline aqueous esterification for thiol–ene click functionalization</atitle><jtitle>Materials letters</jtitle><date>2019-06-15</date><risdate>2019</risdate><volume>245</volume><spage>18</spage><epage>21</epage><pages>18-21</pages><issn>0167-577X</issn><eissn>1873-4979</eissn><abstract>•Facile methacrylation of cellulose was realized by alkaline aqueous esterification.•Obtained methacrylated cellulose is feasible for thiol–ene click functionalization.•Our strategy enables thiolated functional groups easily to graft cellulose.
In this contribution, alkaline carbonates were used as catalyst to develop an one-pot approach for esterification between cellulose and methacrylate anhydrides in aqueous solution. FTIR, 13C CP/MAS NMR and XRD analysis revealed successful esterification in amorphous domains of cellulose without affecting the cellulose crystal structure. The obtained methacrylated cellulose was amenable to further functionalization via thiol–ene click reactions. After this esterification under alkaline aqueous condition, cellulose can be easily grafted with thiolated motifs including fluorophores and bioactive peptide. Our work demonstrates an easy strategy for cellulose modification and functionalization and will greatly promote the wide-spread applications of cellulose-based materials.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.matlet.2019.02.083</doi><tpages>4</tpages></addata></record> |
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| subjects | Anhydrides Aqueous esterification Aqueous solutions Biomaterials Carbon 13 Carbonates Cellulose Cellulose esters Chemical compounds Crystal structure Crystals Domains Esterification Fluorescence Functional Materials science NMR spectroscopy Thiol−ene |
| title | Facile methacrylation of cellulose via alkaline aqueous esterification for thiol–ene click functionalization |
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