Photodimerization and Polymerization of PEG Derivatives through Radical Coupling using Photochemistry of Dithiocarbamate
This article reports the development of a novel polymerization based on the photochemistry of benzyl N , N -diethydithiocarbamate (BDC), which dissociates to a pair of radicals, benzyl radicals and dithiocarbamyl radicals, by ultraviolet light (UV) irradiation. Upon UV irradiation to a N , N -dimeth...
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| Veröffentlicht in: | Polymer journal 2008-11, Vol.40 (11), p.1060-1066 |
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| creator | Nakayama, Yasuhide Ishikawa, Ayaka Sato, Ryo Uchida, Kingo Kambe, Nobuaki |
| description | This article reports the development of a novel polymerization based on the photochemistry of benzyl
N
,
N
-diethydithiocarbamate (BDC), which dissociates to a pair of radicals, benzyl radicals and dithiocarbamyl radicals, by ultraviolet light (UV) irradiation. Upon UV irradiation to a
N
,
N
-dimethylformamide (DMF) solution with extremely thin thickness containing mono-BDC-derivatized poly(ethylene glycol) (PEG) dimerization of the PEG derivative occurred due to bibenzyl bond formation by radical coupling between benzyl radicals generated in the terminal of the PEG derivative. The reaction rate was about 90% by several tenth minutes of irradiation. On the other hand, UV irradiation of a DMF solution of bis-BDC-derivatized PEG produced high molecular weight PEG derivatives by inter-molecularly coupling between diradicals, which have benzyl radicals at both terminals of the PEG derivative. The products had alternative structure of PEG chain and bibenzyl bond. The chain length of the produced polymer grew with irradiation time. The reaction rate rapidly increased at higher light intensities, and further increased at shorter optical distance of the solution to reach about 90% by several tenth minutes of irradiation. Possibility and limitation of this polymerization method was discussed. |
| doi_str_mv | 10.1295/polymj.PJ2008132 |
| format | Article |
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N
,
N
-diethydithiocarbamate (BDC), which dissociates to a pair of radicals, benzyl radicals and dithiocarbamyl radicals, by ultraviolet light (UV) irradiation. Upon UV irradiation to a
N
,
N
-dimethylformamide (DMF) solution with extremely thin thickness containing mono-BDC-derivatized poly(ethylene glycol) (PEG) dimerization of the PEG derivative occurred due to bibenzyl bond formation by radical coupling between benzyl radicals generated in the terminal of the PEG derivative. The reaction rate was about 90% by several tenth minutes of irradiation. On the other hand, UV irradiation of a DMF solution of bis-BDC-derivatized PEG produced high molecular weight PEG derivatives by inter-molecularly coupling between diradicals, which have benzyl radicals at both terminals of the PEG derivative. The products had alternative structure of PEG chain and bibenzyl bond. The chain length of the produced polymer grew with irradiation time. The reaction rate rapidly increased at higher light intensities, and further increased at shorter optical distance of the solution to reach about 90% by several tenth minutes of irradiation. Possibility and limitation of this polymerization method was discussed.</description><identifier>ISSN: 0032-3896</identifier><identifier>EISSN: 1349-0540</identifier><identifier>DOI: 10.1295/polymj.PJ2008132</identifier><identifier>CODEN: POLJB8</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>Applied sciences ; Biomaterials ; Bioorganic Chemistry ; Bonding ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Coupling (molecular) ; Derivatives ; Exact sciences and technology ; Irradiation ; Photochemistry ; Physicochemistry of polymers ; Polymer Sciences ; Polymerization ; Polymers and radiations ; Radicals ; regular-article ; Surfaces and Interfaces ; Terminals ; Thin Films</subject><ispartof>Polymer journal, 2008-11, Vol.40 (11), p.1060-1066</ispartof><rights>The Society of Polymer Science, Japan 2008</rights><rights>2009 INIST-CNRS</rights><rights>Copyright Nature Publishing Group Nov 2008</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c509t-309bf0b7bf83aaa38037714a76aa3a06a096eec8b6f46761ee75b7b16cd23bb33</citedby><cites>FETCH-LOGICAL-c509t-309bf0b7bf83aaa38037714a76aa3a06a096eec8b6f46761ee75b7b16cd23bb33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20887320$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Nakayama, Yasuhide</creatorcontrib><creatorcontrib>Ishikawa, Ayaka</creatorcontrib><creatorcontrib>Sato, Ryo</creatorcontrib><creatorcontrib>Uchida, Kingo</creatorcontrib><creatorcontrib>Kambe, Nobuaki</creatorcontrib><title>Photodimerization and Polymerization of PEG Derivatives through Radical Coupling using Photochemistry of Dithiocarbamate</title><title>Polymer journal</title><addtitle>Polym J</addtitle><description>This article reports the development of a novel polymerization based on the photochemistry of benzyl
N
,
N
-diethydithiocarbamate (BDC), which dissociates to a pair of radicals, benzyl radicals and dithiocarbamyl radicals, by ultraviolet light (UV) irradiation. Upon UV irradiation to a
N
,
N
-dimethylformamide (DMF) solution with extremely thin thickness containing mono-BDC-derivatized poly(ethylene glycol) (PEG) dimerization of the PEG derivative occurred due to bibenzyl bond formation by radical coupling between benzyl radicals generated in the terminal of the PEG derivative. The reaction rate was about 90% by several tenth minutes of irradiation. On the other hand, UV irradiation of a DMF solution of bis-BDC-derivatized PEG produced high molecular weight PEG derivatives by inter-molecularly coupling between diradicals, which have benzyl radicals at both terminals of the PEG derivative. The products had alternative structure of PEG chain and bibenzyl bond. The chain length of the produced polymer grew with irradiation time. The reaction rate rapidly increased at higher light intensities, and further increased at shorter optical distance of the solution to reach about 90% by several tenth minutes of irradiation. Possibility and limitation of this polymerization method was discussed.</description><subject>Applied sciences</subject><subject>Biomaterials</subject><subject>Bioorganic Chemistry</subject><subject>Bonding</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Coupling (molecular)</subject><subject>Derivatives</subject><subject>Exact sciences and technology</subject><subject>Irradiation</subject><subject>Photochemistry</subject><subject>Physicochemistry of polymers</subject><subject>Polymer Sciences</subject><subject>Polymerization</subject><subject>Polymers and radiations</subject><subject>Radicals</subject><subject>regular-article</subject><subject>Surfaces and Interfaces</subject><subject>Terminals</subject><subject>Thin Films</subject><issn>0032-3896</issn><issn>1349-0540</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNp1kd1LwzAUxYMoOD_efSyI4Ev1JmnT5lHmN4JD9LncZuma0TYzaYfzrzdzoiL4kpCT3z0c7iHkiMIZZTI9X9hm1c7PJvcMIKecbZER5YmMIU1gm4wAOIt5LsUu2fN-DsBECsmIvE1q29upabUz79gb20XYTaPJ2u1HslU0ubqJLoOyDMpS-6ivnR1mdfSEU6OwicZ2WDSmm0WDX5-ftqrWrfG9W60NLk1fG6vQldhirw_IToWN14df9z55ub56Ht_GD483d-OLh1ilIPuYgywrKLOyyjki8hx4ltEEMxEeCAJBCq1VXooqEZmgWmdpoKlQU8bLkvN9crrxXTj7OmjfFyGS0k2DnbaDL2jCZZYKyfKAHv9B53ZwXUhXUGBSBpQlgYINpZz13umqWDjTolsFqFhXUWyqKL6rCCMnX8bow64qh50y_nuOQZ5nnEHg6Ibz4aubafc7wD_eH9Flncw</recordid><startdate>20081101</startdate><enddate>20081101</enddate><creator>Nakayama, Yasuhide</creator><creator>Ishikawa, Ayaka</creator><creator>Sato, Ryo</creator><creator>Uchida, Kingo</creator><creator>Kambe, Nobuaki</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7SP</scope><scope>L7M</scope></search><sort><creationdate>20081101</creationdate><title>Photodimerization and Polymerization of PEG Derivatives through Radical Coupling using Photochemistry of Dithiocarbamate</title><author>Nakayama, Yasuhide ; Ishikawa, Ayaka ; Sato, Ryo ; Uchida, Kingo ; Kambe, Nobuaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c509t-309bf0b7bf83aaa38037714a76aa3a06a096eec8b6f46761ee75b7b16cd23bb33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Applied sciences</topic><topic>Biomaterials</topic><topic>Bioorganic Chemistry</topic><topic>Bonding</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Coupling (molecular)</topic><topic>Derivatives</topic><topic>Exact sciences and technology</topic><topic>Irradiation</topic><topic>Photochemistry</topic><topic>Physicochemistry of polymers</topic><topic>Polymer Sciences</topic><topic>Polymerization</topic><topic>Polymers and radiations</topic><topic>Radicals</topic><topic>regular-article</topic><topic>Surfaces and Interfaces</topic><topic>Terminals</topic><topic>Thin Films</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nakayama, Yasuhide</creatorcontrib><creatorcontrib>Ishikawa, Ayaka</creatorcontrib><creatorcontrib>Sato, Ryo</creatorcontrib><creatorcontrib>Uchida, Kingo</creatorcontrib><creatorcontrib>Kambe, Nobuaki</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>Electronics & Communications Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Polymer journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nakayama, Yasuhide</au><au>Ishikawa, Ayaka</au><au>Sato, Ryo</au><au>Uchida, Kingo</au><au>Kambe, Nobuaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photodimerization and Polymerization of PEG Derivatives through Radical Coupling using Photochemistry of Dithiocarbamate</atitle><jtitle>Polymer journal</jtitle><stitle>Polym J</stitle><date>2008-11-01</date><risdate>2008</risdate><volume>40</volume><issue>11</issue><spage>1060</spage><epage>1066</epage><pages>1060-1066</pages><issn>0032-3896</issn><eissn>1349-0540</eissn><coden>POLJB8</coden><abstract>This article reports the development of a novel polymerization based on the photochemistry of benzyl
N
,
N
-diethydithiocarbamate (BDC), which dissociates to a pair of radicals, benzyl radicals and dithiocarbamyl radicals, by ultraviolet light (UV) irradiation. Upon UV irradiation to a
N
,
N
-dimethylformamide (DMF) solution with extremely thin thickness containing mono-BDC-derivatized poly(ethylene glycol) (PEG) dimerization of the PEG derivative occurred due to bibenzyl bond formation by radical coupling between benzyl radicals generated in the terminal of the PEG derivative. The reaction rate was about 90% by several tenth minutes of irradiation. On the other hand, UV irradiation of a DMF solution of bis-BDC-derivatized PEG produced high molecular weight PEG derivatives by inter-molecularly coupling between diradicals, which have benzyl radicals at both terminals of the PEG derivative. The products had alternative structure of PEG chain and bibenzyl bond. The chain length of the produced polymer grew with irradiation time. The reaction rate rapidly increased at higher light intensities, and further increased at shorter optical distance of the solution to reach about 90% by several tenth minutes of irradiation. Possibility and limitation of this polymerization method was discussed.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><doi>10.1295/polymj.PJ2008132</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Applied sciences Biomaterials Bioorganic Chemistry Bonding Chemistry Chemistry and Materials Science Chemistry/Food Science Coupling (molecular) Derivatives Exact sciences and technology Irradiation Photochemistry Physicochemistry of polymers Polymer Sciences Polymerization Polymers and radiations Radicals regular-article Surfaces and Interfaces Terminals Thin Films |
| title | Photodimerization and Polymerization of PEG Derivatives through Radical Coupling using Photochemistry of Dithiocarbamate |
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