Naphthoquinone-based imidazolyl esters as blue-light-sensitive Type I photoinitiators
In this work, a series of Type I photoinitiators (PIs), based on the naphthoquinone scaffold, were designed and synthesized for the first time in order to induce photopolymerization under visible light. As a result, these PIs exhibit excellent photoinitiation abilities in the presence of acrylate mo...
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| Veröffentlicht in: | Polymer chemistry 2022-08, Vol.13 (33), p.4817-4831 |
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| container_title | Polymer chemistry |
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| creator | Hammoud, Fatima Pavlou, Aristea Petropoulos, Alexandros Graff, Bernadette Siskos, Michael G Hijazi, Akram Morlet-Savary, Fabrice Dumur, Frédéric Lalevée, Jacques |
| description | In this work, a series of Type I photoinitiators (PIs), based on the naphthoquinone scaffold, were designed and synthesized for the first time in order to induce photopolymerization under visible light. As a result, these PIs exhibit excellent photoinitiation abilities in the presence of acrylate monomers upon LED@405 or @455 nm irradiation. Interestingly, some compounds have better photoinitiation performance than the benchmark Type I phosphine-oxide,
i.e.
diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) upon exposure to LED@455 nm. Chemical mechanisms supporting the photopolymerization process were investigated through different techniques as well as theoretical calculations. In addition, the newly proposed structures were also investigated in two-component photoinitiating systems and exhibited a higher efficiency in free radical photopolymerization. Finally, a direct laser writing approach was successfully used to fabricate 3D objects.
In this work, a series of Type I photoinitiators (PIs), based on the naphthoquinone scaffold, were designed and synthesized for the first time in order to induce photopolymerization under visible light. |
| doi_str_mv | 10.1039/d2py00753c |
| format | Article |
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i.e.
diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) upon exposure to LED@455 nm. Chemical mechanisms supporting the photopolymerization process were investigated through different techniques as well as theoretical calculations. In addition, the newly proposed structures were also investigated in two-component photoinitiating systems and exhibited a higher efficiency in free radical photopolymerization. Finally, a direct laser writing approach was successfully used to fabricate 3D objects.
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i.e.
diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) upon exposure to LED@455 nm. Chemical mechanisms supporting the photopolymerization process were investigated through different techniques as well as theoretical calculations. In addition, the newly proposed structures were also investigated in two-component photoinitiating systems and exhibited a higher efficiency in free radical photopolymerization. Finally, a direct laser writing approach was successfully used to fabricate 3D objects.
In this work, a series of Type I photoinitiators (PIs), based on the naphthoquinone scaffold, were designed and synthesized for the first time in order to induce photopolymerization under visible light.</description><subject>Chemical Sciences</subject><subject>Direct laser writing</subject><subject>Esters</subject><subject>Free radicals</subject><subject>Material chemistry</subject><subject>Phosphine oxide</subject><subject>Photoinitiators</subject><subject>Photopolymerization</subject><subject>Polymer chemistry</subject><issn>1759-9954</issn><issn>1759-9962</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpFkctLw0AQxhdRsNRevAsBTwrRfWR3k2OpjxaKeqgHT8smmZgtaTbupoX417u1Uucywzc_PuaB0CXBdwSz7L6k3YCx5Kw4QSMieRZnmaCnx5on52ji_RqHYCShTIzQ-4vu6r62X1vT2hbiXHsoI7Mxpf62zdBE4HtwPtI-ypstxI35rPvYQ-tNb3YQrYYOokXU1ba3pg2a7q3zF-is0o2HyV8eo9XT42o2j5evz4vZdBkXjJM-BkEJSaTgRKRSgC4J5JKICqo0qxJZ5IRVugwdLjRNC6ZJJqQGBjnJSVqxMbo52Na6UZ0zG-0GZbVR8-lS7TXMpKCS8R0J7PWB7VxYNmyl1nbr2jCdohJzllJGeaBuD1ThrPcOqqMtwWp_ZPVA3z5-jzwL8NUBdr44cv9PYD_buHku</recordid><startdate>20220823</startdate><enddate>20220823</enddate><creator>Hammoud, Fatima</creator><creator>Pavlou, Aristea</creator><creator>Petropoulos, Alexandros</creator><creator>Graff, Bernadette</creator><creator>Siskos, Michael G</creator><creator>Hijazi, Akram</creator><creator>Morlet-Savary, Fabrice</creator><creator>Dumur, Frédéric</creator><creator>Lalevée, Jacques</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/0000-0003-3068-5170</orcidid><orcidid>https://orcid.org/0000-0001-9297-0335</orcidid><orcidid>https://orcid.org/0000-0003-4872-094X</orcidid></search><sort><creationdate>20220823</creationdate><title>Naphthoquinone-based imidazolyl esters as blue-light-sensitive Type I photoinitiators</title><author>Hammoud, Fatima ; Pavlou, Aristea ; Petropoulos, Alexandros ; Graff, Bernadette ; Siskos, Michael G ; Hijazi, Akram ; Morlet-Savary, Fabrice ; Dumur, Frédéric ; Lalevée, Jacques</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-e6211476516876ead1eb716fef89f47cb13fad76e56a28c3a1967ae3eb1b18f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Chemical Sciences</topic><topic>Direct laser writing</topic><topic>Esters</topic><topic>Free radicals</topic><topic>Material chemistry</topic><topic>Phosphine oxide</topic><topic>Photoinitiators</topic><topic>Photopolymerization</topic><topic>Polymer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hammoud, Fatima</creatorcontrib><creatorcontrib>Pavlou, Aristea</creatorcontrib><creatorcontrib>Petropoulos, Alexandros</creatorcontrib><creatorcontrib>Graff, Bernadette</creatorcontrib><creatorcontrib>Siskos, Michael G</creatorcontrib><creatorcontrib>Hijazi, Akram</creatorcontrib><creatorcontrib>Morlet-Savary, Fabrice</creatorcontrib><creatorcontrib>Dumur, Frédéric</creatorcontrib><creatorcontrib>Lalevée, Jacques</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>Hammoud, Fatima</au><au>Pavlou, Aristea</au><au>Petropoulos, Alexandros</au><au>Graff, Bernadette</au><au>Siskos, Michael G</au><au>Hijazi, Akram</au><au>Morlet-Savary, Fabrice</au><au>Dumur, Frédéric</au><au>Lalevée, Jacques</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Naphthoquinone-based imidazolyl esters as blue-light-sensitive Type I photoinitiators</atitle><jtitle>Polymer chemistry</jtitle><date>2022-08-23</date><risdate>2022</risdate><volume>13</volume><issue>33</issue><spage>4817</spage><epage>4831</epage><pages>4817-4831</pages><issn>1759-9954</issn><eissn>1759-9962</eissn><abstract>In this work, a series of Type I photoinitiators (PIs), based on the naphthoquinone scaffold, were designed and synthesized for the first time in order to induce photopolymerization under visible light. As a result, these PIs exhibit excellent photoinitiation abilities in the presence of acrylate monomers upon LED@405 or @455 nm irradiation. Interestingly, some compounds have better photoinitiation performance than the benchmark Type I phosphine-oxide,
i.e.
diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) upon exposure to LED@455 nm. Chemical mechanisms supporting the photopolymerization process were investigated through different techniques as well as theoretical calculations. In addition, the newly proposed structures were also investigated in two-component photoinitiating systems and exhibited a higher efficiency in free radical photopolymerization. Finally, a direct laser writing approach was successfully used to fabricate 3D objects.
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| ispartof | Polymer chemistry, 2022-08, Vol.13 (33), p.4817-4831 |
| issn | 1759-9954 1759-9962 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Chemical Sciences Direct laser writing Esters Free radicals Material chemistry Phosphine oxide Photoinitiators Photopolymerization Polymer chemistry |
| title | Naphthoquinone-based imidazolyl esters as blue-light-sensitive Type I photoinitiators |
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