RAFT‐Mediated Emulsion Polymerization‐Induced Self‐Assembly for the Synthesis of Core‐Degradable Waterborne Particles
Poly(N‐acryloylmorpholine) (PNAM)‐decorated waterborne nanoparticles comprising a core of either degradable polystyrene (PS) or poly(n‐butyl acrylate) (PBA) were synthesized by polymerization‐induced self‐assembly (PISA) in water. A PNAM bearing a trithiocarbonate chain end (PNAM‐TTC) was extended v...
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| creator | Galanopoulo, Paul Gil, Noémie Gigmes, Didier Lefay, Catherine Guillaneuf, Yohann Lages, Maëlle Nicolas, Julien D'Agosto, Franck Lansalot, Muriel |
| description | Poly(N‐acryloylmorpholine) (PNAM)‐decorated waterborne nanoparticles comprising a core of either degradable polystyrene (PS) or poly(n‐butyl acrylate) (PBA) were synthesized by polymerization‐induced self‐assembly (PISA) in water. A PNAM bearing a trithiocarbonate chain end (PNAM‐TTC) was extended via reversible addition‐fragmentation chain transfer (RAFT)‐mediated emulsion copolymerization of either styrene (S) or n‐butyl acrylate (BA) with dibenzo[c,e]oxepane‐5‐thione (DOT). Well‐defined amphiphilic block copolymers were obtained. The in situ self‐assembly of these polymers resulted in the formation of stable nanoparticles. The insertion of thioester units in the vinylic blocks enabled their degradation under basic conditions. The same strategy was then applied to the emulsion copolymerization of BA with DOT using a poly(ethylene glycol) (PEG) equipped with a trithiocarbonate end group, resulting in PEG‐decorated nanoparticles with degradable PBA‐based cores.
Emulsion copolymerization of dibenzo[c,e]oxepane‐5‐thione (DOT) with either styrene or n‐butyl acrylate was carried out in water to produce block copolymer nanoparticles via RAFT‐mediated PISA in emulsion. Hydrophilic blocks are either poly(N‐acryloylmorpholine) or poly(ethylene glycol), two polymers largely used for their known biocompatibility. The degradability of the hydrophobic core block is ensured by in‐chain cleavable thioester functions. |
| doi_str_mv | 10.1002/anie.202302093 |
| format | Article |
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Emulsion copolymerization of dibenzo[c,e]oxepane‐5‐thione (DOT) with either styrene or n‐butyl acrylate was carried out in water to produce block copolymer nanoparticles via RAFT‐mediated PISA in emulsion. Hydrophilic blocks are either poly(N‐acryloylmorpholine) or poly(ethylene glycol), two polymers largely used for their known biocompatibility. The degradability of the hydrophobic core block is ensured by in‐chain cleavable thioester functions.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202302093</identifier><identifier>PMID: 36821431</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Block copolymers ; Chain transfer ; Chemical Sciences ; Copolymerization ; Degradable Polymers ; Degradation ; Emulsion ; Emulsion polymerization ; Nanoparticles ; PISA ; Polyethylene glycol ; Polymerization ; Polymers ; Polystyrene ; Polystyrene resins ; Self-assembly ; Styrene ; Thionolactone</subject><ispartof>Angewandte Chemie International Edition, 2023-04, Vol.62 (16), p.e202302093-n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2023 Wiley-VCH GmbH.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4473-4c7bd04c1c7f7616ac10f499effd1496884c93afa4278d57aebaaacfc6d4aeb53</citedby><cites>FETCH-LOGICAL-c4473-4c7bd04c1c7f7616ac10f499effd1496884c93afa4278d57aebaaacfc6d4aeb53</cites><orcidid>0000-0002-1597-0873 ; 0000-0002-5390-1553 ; 0000-0001-8989-2962 ; 0000-0002-8833-8393 ; 0000-0003-2730-869X ; 0000-0001-9010-6746 ; 0000-0003-3504-0232</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.202302093$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202302093$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36821431$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-04028559$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Galanopoulo, Paul</creatorcontrib><creatorcontrib>Gil, Noémie</creatorcontrib><creatorcontrib>Gigmes, Didier</creatorcontrib><creatorcontrib>Lefay, Catherine</creatorcontrib><creatorcontrib>Guillaneuf, Yohann</creatorcontrib><creatorcontrib>Lages, Maëlle</creatorcontrib><creatorcontrib>Nicolas, Julien</creatorcontrib><creatorcontrib>D'Agosto, Franck</creatorcontrib><creatorcontrib>Lansalot, Muriel</creatorcontrib><title>RAFT‐Mediated Emulsion Polymerization‐Induced Self‐Assembly for the Synthesis of Core‐Degradable Waterborne Particles</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Poly(N‐acryloylmorpholine) (PNAM)‐decorated waterborne nanoparticles comprising a core of either degradable polystyrene (PS) or poly(n‐butyl acrylate) (PBA) were synthesized by polymerization‐induced self‐assembly (PISA) in water. A PNAM bearing a trithiocarbonate chain end (PNAM‐TTC) was extended via reversible addition‐fragmentation chain transfer (RAFT)‐mediated emulsion copolymerization of either styrene (S) or n‐butyl acrylate (BA) with dibenzo[c,e]oxepane‐5‐thione (DOT). Well‐defined amphiphilic block copolymers were obtained. The in situ self‐assembly of these polymers resulted in the formation of stable nanoparticles. The insertion of thioester units in the vinylic blocks enabled their degradation under basic conditions. The same strategy was then applied to the emulsion copolymerization of BA with DOT using a poly(ethylene glycol) (PEG) equipped with a trithiocarbonate end group, resulting in PEG‐decorated nanoparticles with degradable PBA‐based cores.
Emulsion copolymerization of dibenzo[c,e]oxepane‐5‐thione (DOT) with either styrene or n‐butyl acrylate was carried out in water to produce block copolymer nanoparticles via RAFT‐mediated PISA in emulsion. Hydrophilic blocks are either poly(N‐acryloylmorpholine) or poly(ethylene glycol), two polymers largely used for their known biocompatibility. The degradability of the hydrophobic core block is ensured by in‐chain cleavable thioester functions.</description><subject>Block copolymers</subject><subject>Chain transfer</subject><subject>Chemical Sciences</subject><subject>Copolymerization</subject><subject>Degradable Polymers</subject><subject>Degradation</subject><subject>Emulsion</subject><subject>Emulsion polymerization</subject><subject>Nanoparticles</subject><subject>PISA</subject><subject>Polyethylene glycol</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Polystyrene</subject><subject>Polystyrene resins</subject><subject>Self-assembly</subject><subject>Styrene</subject><subject>Thionolactone</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqF0c1u1DAQB_AIgWgpXDmiSFzgkMWOnTg-rpYtXWmBihZxtBxnTF05cWsnoCAh8Qg8I0_CrLYsEhdO_vr5r7Eny55SsqCElK_04GBRkpKRkkh2LzumVUkLJgS7j3POWCGaih5lj1K6Rt80pH6YHbG6KfGQHmffPyxPL3_9-PkWOqdH6PJ1P_nkwpCfBz_3EN03PeISyWboJoPiArzF5TIl6Fs_5zbEfLyC_GIecEgu5cHmqxAB0Wv4HHWnWw_5J4yPbYgD5Oc6js54SI-zB1b7BE_uxpPs4-n6cnVWbN-_2ayW28JwLljBjWg7wg01woqa1tpQYrmUYG1HuaybhhvJtNW8FE1XCQ2t1tpYU3cc5xU7yV7uc6-0VzfR9TrOKminzpZbtdsjHP-mquQXivbF3t7EcDtBGlXvkgHv9QBhSqoUQjJe1Ywjff4PvQ5THPAlqCRrJMViUS32ysSQUgR7qIAStWui2jVRHZqIF57dxU5tD92B_-kaArkHX52H-T9xavlus_4b_htHoa2H</recordid><startdate>20230411</startdate><enddate>20230411</enddate><creator>Galanopoulo, Paul</creator><creator>Gil, Noémie</creator><creator>Gigmes, Didier</creator><creator>Lefay, Catherine</creator><creator>Guillaneuf, Yohann</creator><creator>Lages, Maëlle</creator><creator>Nicolas, Julien</creator><creator>D'Agosto, Franck</creator><creator>Lansalot, Muriel</creator><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-1597-0873</orcidid><orcidid>https://orcid.org/0000-0002-5390-1553</orcidid><orcidid>https://orcid.org/0000-0001-8989-2962</orcidid><orcidid>https://orcid.org/0000-0002-8833-8393</orcidid><orcidid>https://orcid.org/0000-0003-2730-869X</orcidid><orcidid>https://orcid.org/0000-0001-9010-6746</orcidid><orcidid>https://orcid.org/0000-0003-3504-0232</orcidid></search><sort><creationdate>20230411</creationdate><title>RAFT‐Mediated Emulsion Polymerization‐Induced Self‐Assembly for the Synthesis of Core‐Degradable Waterborne Particles</title><author>Galanopoulo, Paul ; Gil, Noémie ; Gigmes, Didier ; Lefay, Catherine ; Guillaneuf, Yohann ; Lages, Maëlle ; Nicolas, Julien ; D'Agosto, Franck ; Lansalot, Muriel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4473-4c7bd04c1c7f7616ac10f499effd1496884c93afa4278d57aebaaacfc6d4aeb53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Block copolymers</topic><topic>Chain transfer</topic><topic>Chemical Sciences</topic><topic>Copolymerization</topic><topic>Degradable Polymers</topic><topic>Degradation</topic><topic>Emulsion</topic><topic>Emulsion polymerization</topic><topic>Nanoparticles</topic><topic>PISA</topic><topic>Polyethylene glycol</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Polystyrene</topic><topic>Polystyrene resins</topic><topic>Self-assembly</topic><topic>Styrene</topic><topic>Thionolactone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Galanopoulo, Paul</creatorcontrib><creatorcontrib>Gil, Noémie</creatorcontrib><creatorcontrib>Gigmes, Didier</creatorcontrib><creatorcontrib>Lefay, Catherine</creatorcontrib><creatorcontrib>Guillaneuf, Yohann</creatorcontrib><creatorcontrib>Lages, Maëlle</creatorcontrib><creatorcontrib>Nicolas, Julien</creatorcontrib><creatorcontrib>D'Agosto, Franck</creatorcontrib><creatorcontrib>Lansalot, Muriel</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Galanopoulo, Paul</au><au>Gil, Noémie</au><au>Gigmes, Didier</au><au>Lefay, Catherine</au><au>Guillaneuf, Yohann</au><au>Lages, Maëlle</au><au>Nicolas, Julien</au><au>D'Agosto, Franck</au><au>Lansalot, Muriel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>RAFT‐Mediated Emulsion Polymerization‐Induced Self‐Assembly for the Synthesis of Core‐Degradable Waterborne Particles</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2023-04-11</date><risdate>2023</risdate><volume>62</volume><issue>16</issue><spage>e202302093</spage><epage>n/a</epage><pages>e202302093-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Poly(N‐acryloylmorpholine) (PNAM)‐decorated waterborne nanoparticles comprising a core of either degradable polystyrene (PS) or poly(n‐butyl acrylate) (PBA) were synthesized by polymerization‐induced self‐assembly (PISA) in water. A PNAM bearing a trithiocarbonate chain end (PNAM‐TTC) was extended via reversible addition‐fragmentation chain transfer (RAFT)‐mediated emulsion copolymerization of either styrene (S) or n‐butyl acrylate (BA) with dibenzo[c,e]oxepane‐5‐thione (DOT). Well‐defined amphiphilic block copolymers were obtained. The in situ self‐assembly of these polymers resulted in the formation of stable nanoparticles. The insertion of thioester units in the vinylic blocks enabled their degradation under basic conditions. The same strategy was then applied to the emulsion copolymerization of BA with DOT using a poly(ethylene glycol) (PEG) equipped with a trithiocarbonate end group, resulting in PEG‐decorated nanoparticles with degradable PBA‐based cores.
Emulsion copolymerization of dibenzo[c,e]oxepane‐5‐thione (DOT) with either styrene or n‐butyl acrylate was carried out in water to produce block copolymer nanoparticles via RAFT‐mediated PISA in emulsion. Hydrophilic blocks are either poly(N‐acryloylmorpholine) or poly(ethylene glycol), two polymers largely used for their known biocompatibility. The degradability of the hydrophobic core block is ensured by in‐chain cleavable thioester functions.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36821431</pmid><doi>10.1002/anie.202302093</doi><tpages>9</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-1597-0873</orcidid><orcidid>https://orcid.org/0000-0002-5390-1553</orcidid><orcidid>https://orcid.org/0000-0001-8989-2962</orcidid><orcidid>https://orcid.org/0000-0002-8833-8393</orcidid><orcidid>https://orcid.org/0000-0003-2730-869X</orcidid><orcidid>https://orcid.org/0000-0001-9010-6746</orcidid><orcidid>https://orcid.org/0000-0003-3504-0232</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Block copolymers Chain transfer Chemical Sciences Copolymerization Degradable Polymers Degradation Emulsion Emulsion polymerization Nanoparticles PISA Polyethylene glycol Polymerization Polymers Polystyrene Polystyrene resins Self-assembly Styrene Thionolactone |
| title | RAFT‐Mediated Emulsion Polymerization‐Induced Self‐Assembly for the Synthesis of Core‐Degradable Waterborne Particles |
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