Highly transparent and photopatternable spirobifluorene-based polythioethers with high refractive indices via thiol-ene click chemistry
A series of polythioethers with spirobifluorene skeletons was successfully synthesized by a thiol-ene reaction. A spirobifluorene-containing diacrylate (2,2′-diacryloyloxy-9,9′-spirobifluorene, DASF) was designed and reacted with dithiol components to prepare high-refractive-index polymers (1.7169–1...
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| Veröffentlicht in: | Polymer (Guilford) 2021-05, Vol.224, p.123725, Article 123725 |
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| creator | Iino, Shota Sobu, Shigeki Nakabayashi, Kazuhiro Samitsu, Sadaki Mori, Hideharu |
| description | A series of polythioethers with spirobifluorene skeletons was successfully synthesized by a thiol-ene reaction. A spirobifluorene-containing diacrylate (2,2′-diacryloyloxy-9,9′-spirobifluorene, DASF) was designed and reacted with dithiol components to prepare high-refractive-index polymers (1.7169–1.6690) with high transparency (>90% at 400 nm). The poly(phenylene thioether) obtained from DASF with 1,5-naphthalenedithiol exhibited the highest refractive index (1.7169) and a low Abbe number (14.3), while the polymer obtained with 1,3-benzenedithiol showed a high refractive index (1.7112) and a relatively high Abbe number (19.6). The resulting spirobifluorene-containing polythioethers exhibited tunable glass transition temperatures (Tg = 90–164 °C), and high thermal stabilities (Td5 = 297–353 °C). UV nanoimprinting lithography using rapid thiol-ene photopolymerization of DASF with 1,6-hexanedithiol enabled the successful formation of high-refractive-index polymer nanoimprinted patterns. The presented design strategy allows manipulation of the refractive index and Abbe number, as well as the ability to design molecular structures with suitable aromatic and aliphatic chains between the spirobifluorene units, thus helping to achieve high transparency, flexibility, and thermal stability, in addition to excellent light-induced processability for nano- and microfabrication.
[Display omitted]
•A series of polythioethers with spirobifluorene skeletons was synthesized by a thiol-ene reaction.•A spirobifluorene-containing diacrylate was reacted with dithiols to prepare high-refractive-index polymers (1.7169–1.6690) with high transparency.•The resulting polythioethers exhibited tunable glass transition temperatures (Tg = 90–164 °C) and high thermal stabilities (Td5 = 297–353 °C).•UV nanoimprinting lithography using thiol-ene photopolymerization enabled the formation of high-refractive-index polymer nanoimprinted patterns. |
| doi_str_mv | 10.1016/j.polymer.2021.123725 |
| format | Article |
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[Display omitted]
•A series of polythioethers with spirobifluorene skeletons was synthesized by a thiol-ene reaction.•A spirobifluorene-containing diacrylate was reacted with dithiols to prepare high-refractive-index polymers (1.7169–1.6690) with high transparency.•The resulting polythioethers exhibited tunable glass transition temperatures (Tg = 90–164 °C) and high thermal stabilities (Td5 = 297–353 °C).•UV nanoimprinting lithography using thiol-ene photopolymerization enabled the formation of high-refractive-index polymer nanoimprinted patterns.</description><identifier>ISSN: 0032-3861</identifier><identifier>EISSN: 1873-2291</identifier><identifier>DOI: 10.1016/j.polymer.2021.123725</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Abbe number ; Chemical synthesis ; Glass transition temperature ; High refractive index polymer ; Molecular chains ; Molecular structure ; Photopolymerization ; Polymers ; Polythioether ; Refractivity ; Spirobifluorene ; Temperature ; Thermal stability ; Thiol-ene reaction ; Transition temperatures ; Transparent polymers ; UV nanoimprinting</subject><ispartof>Polymer (Guilford), 2021-05, Vol.224, p.123725, Article 123725</ispartof><rights>2021 Elsevier Ltd</rights><rights>Copyright Elsevier BV May 14, 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-7aaea8c4906127158d057dbf53d0a81a6b02f6010f85d9440e71395ca22837a63</citedby><cites>FETCH-LOGICAL-c384t-7aaea8c4906127158d057dbf53d0a81a6b02f6010f85d9440e71395ca22837a63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0032386121003487$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids></links><search><creatorcontrib>Iino, Shota</creatorcontrib><creatorcontrib>Sobu, Shigeki</creatorcontrib><creatorcontrib>Nakabayashi, Kazuhiro</creatorcontrib><creatorcontrib>Samitsu, Sadaki</creatorcontrib><creatorcontrib>Mori, Hideharu</creatorcontrib><title>Highly transparent and photopatternable spirobifluorene-based polythioethers with high refractive indices via thiol-ene click chemistry</title><title>Polymer (Guilford)</title><description>A series of polythioethers with spirobifluorene skeletons was successfully synthesized by a thiol-ene reaction. A spirobifluorene-containing diacrylate (2,2′-diacryloyloxy-9,9′-spirobifluorene, DASF) was designed and reacted with dithiol components to prepare high-refractive-index polymers (1.7169–1.6690) with high transparency (>90% at 400 nm). The poly(phenylene thioether) obtained from DASF with 1,5-naphthalenedithiol exhibited the highest refractive index (1.7169) and a low Abbe number (14.3), while the polymer obtained with 1,3-benzenedithiol showed a high refractive index (1.7112) and a relatively high Abbe number (19.6). The resulting spirobifluorene-containing polythioethers exhibited tunable glass transition temperatures (Tg = 90–164 °C), and high thermal stabilities (Td5 = 297–353 °C). UV nanoimprinting lithography using rapid thiol-ene photopolymerization of DASF with 1,6-hexanedithiol enabled the successful formation of high-refractive-index polymer nanoimprinted patterns. The presented design strategy allows manipulation of the refractive index and Abbe number, as well as the ability to design molecular structures with suitable aromatic and aliphatic chains between the spirobifluorene units, thus helping to achieve high transparency, flexibility, and thermal stability, in addition to excellent light-induced processability for nano- and microfabrication.
[Display omitted]
•A series of polythioethers with spirobifluorene skeletons was synthesized by a thiol-ene reaction.•A spirobifluorene-containing diacrylate was reacted with dithiols to prepare high-refractive-index polymers (1.7169–1.6690) with high transparency.•The resulting polythioethers exhibited tunable glass transition temperatures (Tg = 90–164 °C) and high thermal stabilities (Td5 = 297–353 °C).•UV nanoimprinting lithography using thiol-ene photopolymerization enabled the formation of high-refractive-index polymer nanoimprinted patterns.</description><subject>Abbe number</subject><subject>Chemical synthesis</subject><subject>Glass transition temperature</subject><subject>High refractive index polymer</subject><subject>Molecular chains</subject><subject>Molecular structure</subject><subject>Photopolymerization</subject><subject>Polymers</subject><subject>Polythioether</subject><subject>Refractivity</subject><subject>Spirobifluorene</subject><subject>Temperature</subject><subject>Thermal stability</subject><subject>Thiol-ene reaction</subject><subject>Transition temperatures</subject><subject>Transparent polymers</subject><subject>UV nanoimprinting</subject><issn>0032-3861</issn><issn>1873-2291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkM1qGzEUhUVpIG6aRwgIuh7nShrNz6oU08aBQDftWtzR3MnIHY-mkuziJ8hrV8beZ6XF_c4R52PsQcBagKged-vFT6c9hbUEKdZCqlrqD2wlmloVUrbiI1sBKFmophK37FOMOwCQWpYr9rZ1r-N04ingHBcMNCeOc8-X0Se_YEoUZuwm4nFxwXdumA4-Q1R0GClj-eM0Ok9ppBD5P5dGPuZGHmgIaJM7Endz7yxFfnTIz-xU5Dy3k7N_uB1p72IKp8_sZsAp0v31vWO_f3z_tdkWLz-fnjffXgqrmjIVNSJhY8sWKiFroZsedN13g1Y9YCOw6kAOFQgYGt23ZQlUC9Vqi1I2qsZK3bEvl94l-L8Hisns_CFPnKKRWrVKqBpUpvSFssHHmLeYJbg9hpMRYM7Ozc5cnZuzc3NxnnNfLznKE44uX6N1NFvqXSCbTO_dOw3_AfJ2kIk</recordid><startdate>20210514</startdate><enddate>20210514</enddate><creator>Iino, Shota</creator><creator>Sobu, Shigeki</creator><creator>Nakabayashi, Kazuhiro</creator><creator>Samitsu, Sadaki</creator><creator>Mori, Hideharu</creator><general>Elsevier Ltd</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7T7</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope></search><sort><creationdate>20210514</creationdate><title>Highly transparent and photopatternable spirobifluorene-based polythioethers with high refractive indices via thiol-ene click chemistry</title><author>Iino, Shota ; Sobu, Shigeki ; Nakabayashi, Kazuhiro ; Samitsu, Sadaki ; Mori, Hideharu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-7aaea8c4906127158d057dbf53d0a81a6b02f6010f85d9440e71395ca22837a63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Abbe number</topic><topic>Chemical synthesis</topic><topic>Glass transition temperature</topic><topic>High refractive index polymer</topic><topic>Molecular chains</topic><topic>Molecular structure</topic><topic>Photopolymerization</topic><topic>Polymers</topic><topic>Polythioether</topic><topic>Refractivity</topic><topic>Spirobifluorene</topic><topic>Temperature</topic><topic>Thermal stability</topic><topic>Thiol-ene reaction</topic><topic>Transition temperatures</topic><topic>Transparent polymers</topic><topic>UV nanoimprinting</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Iino, Shota</creatorcontrib><creatorcontrib>Sobu, Shigeki</creatorcontrib><creatorcontrib>Nakabayashi, Kazuhiro</creatorcontrib><creatorcontrib>Samitsu, Sadaki</creatorcontrib><creatorcontrib>Mori, Hideharu</creatorcontrib><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Polymer (Guilford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Iino, Shota</au><au>Sobu, Shigeki</au><au>Nakabayashi, Kazuhiro</au><au>Samitsu, Sadaki</au><au>Mori, Hideharu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly transparent and photopatternable spirobifluorene-based polythioethers with high refractive indices via thiol-ene click chemistry</atitle><jtitle>Polymer (Guilford)</jtitle><date>2021-05-14</date><risdate>2021</risdate><volume>224</volume><spage>123725</spage><pages>123725-</pages><artnum>123725</artnum><issn>0032-3861</issn><eissn>1873-2291</eissn><abstract>A series of polythioethers with spirobifluorene skeletons was successfully synthesized by a thiol-ene reaction. A spirobifluorene-containing diacrylate (2,2′-diacryloyloxy-9,9′-spirobifluorene, DASF) was designed and reacted with dithiol components to prepare high-refractive-index polymers (1.7169–1.6690) with high transparency (>90% at 400 nm). The poly(phenylene thioether) obtained from DASF with 1,5-naphthalenedithiol exhibited the highest refractive index (1.7169) and a low Abbe number (14.3), while the polymer obtained with 1,3-benzenedithiol showed a high refractive index (1.7112) and a relatively high Abbe number (19.6). The resulting spirobifluorene-containing polythioethers exhibited tunable glass transition temperatures (Tg = 90–164 °C), and high thermal stabilities (Td5 = 297–353 °C). UV nanoimprinting lithography using rapid thiol-ene photopolymerization of DASF with 1,6-hexanedithiol enabled the successful formation of high-refractive-index polymer nanoimprinted patterns. The presented design strategy allows manipulation of the refractive index and Abbe number, as well as the ability to design molecular structures with suitable aromatic and aliphatic chains between the spirobifluorene units, thus helping to achieve high transparency, flexibility, and thermal stability, in addition to excellent light-induced processability for nano- and microfabrication.
[Display omitted]
•A series of polythioethers with spirobifluorene skeletons was synthesized by a thiol-ene reaction.•A spirobifluorene-containing diacrylate was reacted with dithiols to prepare high-refractive-index polymers (1.7169–1.6690) with high transparency.•The resulting polythioethers exhibited tunable glass transition temperatures (Tg = 90–164 °C) and high thermal stabilities (Td5 = 297–353 °C).•UV nanoimprinting lithography using thiol-ene photopolymerization enabled the formation of high-refractive-index polymer nanoimprinted patterns.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.polymer.2021.123725</doi><oa>free_for_read</oa></addata></record> |
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| subjects | Abbe number Chemical synthesis Glass transition temperature High refractive index polymer Molecular chains Molecular structure Photopolymerization Polymers Polythioether Refractivity Spirobifluorene Temperature Thermal stability Thiol-ene reaction Transition temperatures Transparent polymers UV nanoimprinting |
| title | Highly transparent and photopatternable spirobifluorene-based polythioethers with high refractive indices via thiol-ene click chemistry |
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