Tuning photosensitized singlet oxygen production from microgels synthesized by polymerization in aqueous dispersed media
Novel sub-micronic photoactive polymer colloids grafted with Rose Bengal (RB) photosensitizer were designed to promote singlet oxygen production from a supported organic photosensitizer. Photooxygenation of fine chemicals under visible light irradiation is considered as a green process. To enhance t...
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| Veröffentlicht in: | Polymer chemistry 2019-06, Vol.1 (23), p.317-3179 |
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| creator | Petrizza, Luca Le Bechec, Mickael Decompte, Emile El Hadri, Hind Lacombe, Sylvie Save, Maud |
| description | Novel sub-micronic photoactive polymer colloids grafted with Rose Bengal (RB) photosensitizer were designed to promote singlet oxygen production from a supported organic photosensitizer. Photooxygenation of fine chemicals under visible light irradiation is considered as a green process. To enhance the overall process sustainability, stable colloidal particles were synthesized by polymerization in aqueous dispersed media with the ability to be transferred into ethanol, recycled by a centrifugation step and reused with no significant decrease of the quantum yield of singlet oxygen production. The microgels were synthesized for the first time by miniemulsion copolymerization of vinyl acetate (VAc),
N
-vinyl caprolactam (VCL), polymerizable vinyl benzyl Rose Bengal (VBRB) monomers and divinyl adipate (DVA) crosslinker. The microgels were characterized by UV-visible spectroscopy and compared with the homologue non-crosslinked polymer in order to discriminate the effect of RB grafted onto the linear polymer from its grafting inside crosslinked microgels. The quantum yields of singlet oxygen production were almost null in water but interestingly in the range of 0.27-0.47 in ethanol. The singlet oxygen quantum yield of these polymer materials is tuned by the aggregation state of VBRB units, hence producing an ON/OFF photosensitizing colloidal system. The absorption and emission spectra of the VBRB containing microgels in water were characteristic of strongly aggregated VBRB, while no evidence of aggregation was observed from the spectra in ethanol. The highest singlet oxygen quantum yield of the linear polymer was correlated with a less aggregated state of RB units compared with the crosslinked microgels. The present RB-based microgels were 20% more resistant to photobleaching than free RB.
Miniemulsion copolymerization of vinyl acetate,
N
-vinylcaprolactam, vinyl benzyl Rose Bengal and divinyl adipate to synthesize switchable photosensitizer-grafted polymer colloids for interfacial photooxygenation reactions. |
| doi_str_mv | 10.1039/c9py00157c |
| format | Article |
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N
-vinyl caprolactam (VCL), polymerizable vinyl benzyl Rose Bengal (VBRB) monomers and divinyl adipate (DVA) crosslinker. The microgels were characterized by UV-visible spectroscopy and compared with the homologue non-crosslinked polymer in order to discriminate the effect of RB grafted onto the linear polymer from its grafting inside crosslinked microgels. The quantum yields of singlet oxygen production were almost null in water but interestingly in the range of 0.27-0.47 in ethanol. The singlet oxygen quantum yield of these polymer materials is tuned by the aggregation state of VBRB units, hence producing an ON/OFF photosensitizing colloidal system. The absorption and emission spectra of the VBRB containing microgels in water were characteristic of strongly aggregated VBRB, while no evidence of aggregation was observed from the spectra in ethanol. The highest singlet oxygen quantum yield of the linear polymer was correlated with a less aggregated state of RB units compared with the crosslinked microgels. The present RB-based microgels were 20% more resistant to photobleaching than free RB.
Miniemulsion copolymerization of vinyl acetate,
N
-vinylcaprolactam, vinyl benzyl Rose Bengal and divinyl adipate to synthesize switchable photosensitizer-grafted polymer colloids for interfacial photooxygenation reactions.</description><identifier>ISSN: 1759-9954</identifier><identifier>EISSN: 1759-9962</identifier><identifier>DOI: 10.1039/c9py00157c</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Agglomeration ; Caprolactam ; Chemical Sciences ; Colloiding ; Copolymerization ; Crosslinking ; Emission spectra ; Ethanol ; Fine chemicals ; Grafting ; Homology ; Light irradiation ; Material chemistry ; Microgels ; Organic chemistry ; Other ; Oxygen production ; Polymer chemistry ; Polymerization ; Polymers ; Singlet oxygen ; Spectrum analysis ; Vinyl acetate</subject><ispartof>Polymer chemistry, 2019-06, Vol.1 (23), p.317-3179</ispartof><rights>Copyright Royal Society of Chemistry 2019</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-c377t-d11ecc9f9db2ce7636e48b7f7c4f88c9f853d5bffebfa40fb129de73531055003</citedby><cites>FETCH-LOGICAL-c377t-d11ecc9f9db2ce7636e48b7f7c4f88c9f853d5bffebfa40fb129de73531055003</cites><orcidid>0000-0002-9154-7559 ; 0000-0003-2704-9528 ; 0000-0002-3623-1981</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,315,781,785,886,27929,27930</link.rule.ids><backlink>$$Uhttps://hal.science/hal-02124366$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Petrizza, Luca</creatorcontrib><creatorcontrib>Le Bechec, Mickael</creatorcontrib><creatorcontrib>Decompte, Emile</creatorcontrib><creatorcontrib>El Hadri, Hind</creatorcontrib><creatorcontrib>Lacombe, Sylvie</creatorcontrib><creatorcontrib>Save, Maud</creatorcontrib><title>Tuning photosensitized singlet oxygen production from microgels synthesized by polymerization in aqueous dispersed media</title><title>Polymer chemistry</title><description>Novel sub-micronic photoactive polymer colloids grafted with Rose Bengal (RB) photosensitizer were designed to promote singlet oxygen production from a supported organic photosensitizer. Photooxygenation of fine chemicals under visible light irradiation is considered as a green process. To enhance the overall process sustainability, stable colloidal particles were synthesized by polymerization in aqueous dispersed media with the ability to be transferred into ethanol, recycled by a centrifugation step and reused with no significant decrease of the quantum yield of singlet oxygen production. The microgels were synthesized for the first time by miniemulsion copolymerization of vinyl acetate (VAc),
N
-vinyl caprolactam (VCL), polymerizable vinyl benzyl Rose Bengal (VBRB) monomers and divinyl adipate (DVA) crosslinker. The microgels were characterized by UV-visible spectroscopy and compared with the homologue non-crosslinked polymer in order to discriminate the effect of RB grafted onto the linear polymer from its grafting inside crosslinked microgels. The quantum yields of singlet oxygen production were almost null in water but interestingly in the range of 0.27-0.47 in ethanol. The singlet oxygen quantum yield of these polymer materials is tuned by the aggregation state of VBRB units, hence producing an ON/OFF photosensitizing colloidal system. The absorption and emission spectra of the VBRB containing microgels in water were characteristic of strongly aggregated VBRB, while no evidence of aggregation was observed from the spectra in ethanol. The highest singlet oxygen quantum yield of the linear polymer was correlated with a less aggregated state of RB units compared with the crosslinked microgels. The present RB-based microgels were 20% more resistant to photobleaching than free RB.
Miniemulsion copolymerization of vinyl acetate,
N
-vinylcaprolactam, vinyl benzyl Rose Bengal and divinyl adipate to synthesize switchable photosensitizer-grafted polymer colloids for interfacial photooxygenation reactions.</description><subject>Agglomeration</subject><subject>Caprolactam</subject><subject>Chemical Sciences</subject><subject>Colloiding</subject><subject>Copolymerization</subject><subject>Crosslinking</subject><subject>Emission spectra</subject><subject>Ethanol</subject><subject>Fine chemicals</subject><subject>Grafting</subject><subject>Homology</subject><subject>Light irradiation</subject><subject>Material chemistry</subject><subject>Microgels</subject><subject>Organic chemistry</subject><subject>Other</subject><subject>Oxygen production</subject><subject>Polymer chemistry</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Singlet oxygen</subject><subject>Spectrum analysis</subject><subject>Vinyl acetate</subject><issn>1759-9954</issn><issn>1759-9962</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kU1LxDAQhosouOhevAsRTwrVpGna5rgsfsGCHvTgKbTJZDfSNjVpZeuvN7sr681cJsz7zDAzbxSdEXxDMOW3kncjxoTl8iCakJzxmPMsOdz_WXocTb3_wOFRkiY0m0Tr16E17RJ1K9tbD603vfkGhXxI1tAjux6X0KLOWTXI3tgWaWcb1Bjp7BJqj_zY9ivw26JqRJ2txwac-S63sGlR-TmAHTxSxnfgfMAaUKY8jY50WXuY_saT6O3-7nX-GC-eH57ms0UsaZ73sSIEpOSaqyqRkGc0g7Socp3LVBdFEApGFau0hkqXKdYVSbiCnDJKMGNhz5Poatd3Vdaic6Yp3ShsacTjbCE2OZyQJKVZ9kUCe7ljw7phat-LDzu4NownkoQWKU8xZoG63lHhBN470Pu2BIuNEWLOX963RswDfL6DnZd77s-ooF_8p4tOafoD_fqT2A</recordid><startdate>20190621</startdate><enddate>20190621</enddate><creator>Petrizza, Luca</creator><creator>Le Bechec, Mickael</creator><creator>Decompte, Emile</creator><creator>El Hadri, Hind</creator><creator>Lacombe, Sylvie</creator><creator>Save, Maud</creator><general>Royal Society of Chemistry</general><general>Royal Society of Chemistry - RSC</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-9154-7559</orcidid><orcidid>https://orcid.org/0000-0003-2704-9528</orcidid><orcidid>https://orcid.org/0000-0002-3623-1981</orcidid></search><sort><creationdate>20190621</creationdate><title>Tuning photosensitized singlet oxygen production from microgels synthesized by polymerization in aqueous dispersed media</title><author>Petrizza, Luca ; Le Bechec, Mickael ; Decompte, Emile ; El Hadri, Hind ; Lacombe, Sylvie ; Save, Maud</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c377t-d11ecc9f9db2ce7636e48b7f7c4f88c9f853d5bffebfa40fb129de73531055003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Agglomeration</topic><topic>Caprolactam</topic><topic>Chemical Sciences</topic><topic>Colloiding</topic><topic>Copolymerization</topic><topic>Crosslinking</topic><topic>Emission spectra</topic><topic>Ethanol</topic><topic>Fine chemicals</topic><topic>Grafting</topic><topic>Homology</topic><topic>Light irradiation</topic><topic>Material chemistry</topic><topic>Microgels</topic><topic>Organic chemistry</topic><topic>Other</topic><topic>Oxygen production</topic><topic>Polymer chemistry</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Singlet oxygen</topic><topic>Spectrum analysis</topic><topic>Vinyl acetate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Petrizza, Luca</creatorcontrib><creatorcontrib>Le Bechec, Mickael</creatorcontrib><creatorcontrib>Decompte, Emile</creatorcontrib><creatorcontrib>El Hadri, Hind</creatorcontrib><creatorcontrib>Lacombe, Sylvie</creatorcontrib><creatorcontrib>Save, Maud</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Polymer chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Petrizza, Luca</au><au>Le Bechec, Mickael</au><au>Decompte, Emile</au><au>El Hadri, Hind</au><au>Lacombe, Sylvie</au><au>Save, Maud</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tuning photosensitized singlet oxygen production from microgels synthesized by polymerization in aqueous dispersed media</atitle><jtitle>Polymer chemistry</jtitle><date>2019-06-21</date><risdate>2019</risdate><volume>1</volume><issue>23</issue><spage>317</spage><epage>3179</epage><pages>317-3179</pages><issn>1759-9954</issn><eissn>1759-9962</eissn><abstract>Novel sub-micronic photoactive polymer colloids grafted with Rose Bengal (RB) photosensitizer were designed to promote singlet oxygen production from a supported organic photosensitizer. Photooxygenation of fine chemicals under visible light irradiation is considered as a green process. To enhance the overall process sustainability, stable colloidal particles were synthesized by polymerization in aqueous dispersed media with the ability to be transferred into ethanol, recycled by a centrifugation step and reused with no significant decrease of the quantum yield of singlet oxygen production. The microgels were synthesized for the first time by miniemulsion copolymerization of vinyl acetate (VAc),
N
-vinyl caprolactam (VCL), polymerizable vinyl benzyl Rose Bengal (VBRB) monomers and divinyl adipate (DVA) crosslinker. The microgels were characterized by UV-visible spectroscopy and compared with the homologue non-crosslinked polymer in order to discriminate the effect of RB grafted onto the linear polymer from its grafting inside crosslinked microgels. The quantum yields of singlet oxygen production were almost null in water but interestingly in the range of 0.27-0.47 in ethanol. The singlet oxygen quantum yield of these polymer materials is tuned by the aggregation state of VBRB units, hence producing an ON/OFF photosensitizing colloidal system. The absorption and emission spectra of the VBRB containing microgels in water were characteristic of strongly aggregated VBRB, while no evidence of aggregation was observed from the spectra in ethanol. The highest singlet oxygen quantum yield of the linear polymer was correlated with a less aggregated state of RB units compared with the crosslinked microgels. The present RB-based microgels were 20% more resistant to photobleaching than free RB.
Miniemulsion copolymerization of vinyl acetate,
N
-vinylcaprolactam, vinyl benzyl Rose Bengal and divinyl adipate to synthesize switchable photosensitizer-grafted polymer colloids for interfacial photooxygenation reactions.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c9py00157c</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-9154-7559</orcidid><orcidid>https://orcid.org/0000-0003-2704-9528</orcidid><orcidid>https://orcid.org/0000-0002-3623-1981</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | Royal Society Of Chemistry Journals |
| subjects | Agglomeration Caprolactam Chemical Sciences Colloiding Copolymerization Crosslinking Emission spectra Ethanol Fine chemicals Grafting Homology Light irradiation Material chemistry Microgels Organic chemistry Other Oxygen production Polymer chemistry Polymerization Polymers Singlet oxygen Spectrum analysis Vinyl acetate |
| title | Tuning photosensitized singlet oxygen production from microgels synthesized by polymerization in aqueous dispersed media |
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