Synthesis of regiocontrolled triarylamine-based polymer with a naphthol unit
Redox-active polytriarylamine with hydroxyl groups is a useful material for optoelectronic applications, especially in the solution-processable multilayer devices. A novel regiocontrolled triarylamine-based polymer, poly(di-5-naphthyl-2-ol)phenylamine, with 2-naphthol units was synthesized via oxida...
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| Veröffentlicht in: | Polymer bulletin (Berlin, Germany) Germany), 2021-02, Vol.78 (2), p.965-979 |
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| container_title | Polymer bulletin (Berlin, Germany) |
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| creator | Lee, Jinhee Park, Jeyoung Choi, Hojung Yoon, Young Rok Seo, Myungeun Song, Sua Kim, Byung-Kwon Kim, Sang Youl |
| description | Redox-active polytriarylamine with hydroxyl groups is a useful material for optoelectronic applications, especially in the solution-processable multilayer devices. A novel regiocontrolled triarylamine-based polymer, poly(di-5-naphthyl-2-ol)phenylamine, with 2-naphthol units was synthesized via oxidative coupling polymerization. Polymerization in tetrahydrofuran using a Cu-amine complex oxidant under O
2
atmosphere produced polymers with number-averaged molecular weights as high as 11,300 g mol
−1
. The structure of the polymer was characterized by
1
H and
13
C NMR spectroscopy, showing that the oxidative coupling polymerization occurred at the outer
ortho
position of the 2-naphthols, preserving the hydroxyl groups. The polymer exhibited good solubility in polar aprotic solvents, with a high thermal stability of 446 °C that corresponded to 5% weight loss. The UV–vis absorption of the polymer was similar to that of DNPA, indicating that the kinked-structured polymer hindered the formation of charge-transfer complexes. These results suggest promising applications of the developed polymer in optoelectronic devices. |
| doi_str_mv | 10.1007/s00289-020-03146-y |
| format | Article |
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2
atmosphere produced polymers with number-averaged molecular weights as high as 11,300 g mol
−1
. The structure of the polymer was characterized by
1
H and
13
C NMR spectroscopy, showing that the oxidative coupling polymerization occurred at the outer
ortho
position of the 2-naphthols, preserving the hydroxyl groups. The polymer exhibited good solubility in polar aprotic solvents, with a high thermal stability of 446 °C that corresponded to 5% weight loss. The UV–vis absorption of the polymer was similar to that of DNPA, indicating that the kinked-structured polymer hindered the formation of charge-transfer complexes. These results suggest promising applications of the developed polymer in optoelectronic devices.</description><identifier>ISSN: 0170-0839</identifier><identifier>EISSN: 1436-2449</identifier><identifier>DOI: 10.1007/s00289-020-03146-y</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Characterization and Evaluation of Materials ; Charge transfer ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chromatography ; Complex Fluids and Microfluidics ; Electrodes ; Fourier transforms ; Hydroxyl groups ; Mechanical properties ; Molecular weight ; Multilayers ; Naphthol ; Nitrogen ; NMR spectroscopy ; Optoelectronic devices ; Organic Chemistry ; Original Paper ; Oxidizing agents ; Physical Chemistry ; Polymer Sciences ; Polymerization ; Polymers ; Soft and Granular Matter ; Solvents ; Tetrahydrofuran ; Thermal stability ; Weight loss</subject><ispartof>Polymer bulletin (Berlin, Germany), 2021-02, Vol.78 (2), p.965-979</ispartof><rights>Springer-Verlag GmbH Germany, part of Springer Nature 2020</rights><rights>Springer-Verlag GmbH Germany, part of Springer Nature 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-9587673c5736634f027f289627b46f0f5247dbf1d82058f90efd0690ce3a0da73</citedby><cites>FETCH-LOGICAL-c356t-9587673c5736634f027f289627b46f0f5247dbf1d82058f90efd0690ce3a0da73</cites><orcidid>0000-0003-4106-1996</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00289-020-03146-y$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2918138274?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,780,784,21387,27923,27924,33743,41487,42556,43804,51318,64384,64388,72340</link.rule.ids></links><search><creatorcontrib>Lee, Jinhee</creatorcontrib><creatorcontrib>Park, Jeyoung</creatorcontrib><creatorcontrib>Choi, Hojung</creatorcontrib><creatorcontrib>Yoon, Young Rok</creatorcontrib><creatorcontrib>Seo, Myungeun</creatorcontrib><creatorcontrib>Song, Sua</creatorcontrib><creatorcontrib>Kim, Byung-Kwon</creatorcontrib><creatorcontrib>Kim, Sang Youl</creatorcontrib><title>Synthesis of regiocontrolled triarylamine-based polymer with a naphthol unit</title><title>Polymer bulletin (Berlin, Germany)</title><addtitle>Polym. Bull</addtitle><description>Redox-active polytriarylamine with hydroxyl groups is a useful material for optoelectronic applications, especially in the solution-processable multilayer devices. A novel regiocontrolled triarylamine-based polymer, poly(di-5-naphthyl-2-ol)phenylamine, with 2-naphthol units was synthesized via oxidative coupling polymerization. Polymerization in tetrahydrofuran using a Cu-amine complex oxidant under O
2
atmosphere produced polymers with number-averaged molecular weights as high as 11,300 g mol
−1
. The structure of the polymer was characterized by
1
H and
13
C NMR spectroscopy, showing that the oxidative coupling polymerization occurred at the outer
ortho
position of the 2-naphthols, preserving the hydroxyl groups. The polymer exhibited good solubility in polar aprotic solvents, with a high thermal stability of 446 °C that corresponded to 5% weight loss. The UV–vis absorption of the polymer was similar to that of DNPA, indicating that the kinked-structured polymer hindered the formation of charge-transfer complexes. These results suggest promising applications of the developed polymer in optoelectronic devices.</description><subject>Characterization and Evaluation of Materials</subject><subject>Charge transfer</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chromatography</subject><subject>Complex Fluids and Microfluidics</subject><subject>Electrodes</subject><subject>Fourier transforms</subject><subject>Hydroxyl groups</subject><subject>Mechanical properties</subject><subject>Molecular weight</subject><subject>Multilayers</subject><subject>Naphthol</subject><subject>Nitrogen</subject><subject>NMR spectroscopy</subject><subject>Optoelectronic devices</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Oxidizing agents</subject><subject>Physical Chemistry</subject><subject>Polymer Sciences</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Soft and Granular Matter</subject><subject>Solvents</subject><subject>Tetrahydrofuran</subject><subject>Thermal stability</subject><subject>Weight loss</subject><issn>0170-0839</issn><issn>1436-2449</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNp9kE1LxDAQhoMouK7-AU8Fz9HJR5P2KIu6woIH9RyybbLN0m1qkkX6741W8OZpmJn3nY8HoWsCtwRA3kUAWtUYKGBghAs8naAF4Uxgynl9ihZAZG5VrD5HFzHuIedCkAXavE5D6kx0sfC2CGbnfOOHFHzfm7ZIwekw9frgBoO3OubS6PvpYELx6VJX6GLQY5c63xfHwaVLdGZ1H83Vb1yi98eHt9Uab16enlf3G9ywUiRcl5UUkjWlZEIwboFKm68XVG65sGBLymW7taStKJSVrcHYFkQNjWEaWi3ZEt3Mc8fgP44mJrX3xzDklYrWpCKsopJnFZ1VTfAxBmPVGNwh_6MIqG9qaqamMjX1Q01N2cRmU8ziYWfC3-h_XF-_RXBC</recordid><startdate>20210201</startdate><enddate>20210201</enddate><creator>Lee, Jinhee</creator><creator>Park, Jeyoung</creator><creator>Choi, Hojung</creator><creator>Yoon, Young Rok</creator><creator>Seo, Myungeun</creator><creator>Song, Sua</creator><creator>Kim, Byung-Kwon</creator><creator>Kim, Sang Youl</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</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>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><orcidid>https://orcid.org/0000-0003-4106-1996</orcidid></search><sort><creationdate>20210201</creationdate><title>Synthesis of regiocontrolled triarylamine-based polymer with a naphthol unit</title><author>Lee, Jinhee ; Park, Jeyoung ; Choi, Hojung ; Yoon, Young Rok ; Seo, Myungeun ; Song, Sua ; Kim, Byung-Kwon ; Kim, Sang Youl</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-9587673c5736634f027f289627b46f0f5247dbf1d82058f90efd0690ce3a0da73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Characterization and Evaluation of Materials</topic><topic>Charge transfer</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chromatography</topic><topic>Complex Fluids and Microfluidics</topic><topic>Electrodes</topic><topic>Fourier transforms</topic><topic>Hydroxyl groups</topic><topic>Mechanical properties</topic><topic>Molecular weight</topic><topic>Multilayers</topic><topic>Naphthol</topic><topic>Nitrogen</topic><topic>NMR spectroscopy</topic><topic>Optoelectronic devices</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Oxidizing agents</topic><topic>Physical Chemistry</topic><topic>Polymer Sciences</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Soft and Granular Matter</topic><topic>Solvents</topic><topic>Tetrahydrofuran</topic><topic>Thermal stability</topic><topic>Weight loss</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Jinhee</creatorcontrib><creatorcontrib>Park, Jeyoung</creatorcontrib><creatorcontrib>Choi, Hojung</creatorcontrib><creatorcontrib>Yoon, Young Rok</creatorcontrib><creatorcontrib>Seo, Myungeun</creatorcontrib><creatorcontrib>Song, Sua</creatorcontrib><creatorcontrib>Kim, Byung-Kwon</creatorcontrib><creatorcontrib>Kim, Sang Youl</creatorcontrib><collection>CrossRef</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 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><jtitle>Polymer bulletin (Berlin, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Jinhee</au><au>Park, Jeyoung</au><au>Choi, Hojung</au><au>Yoon, Young Rok</au><au>Seo, Myungeun</au><au>Song, Sua</au><au>Kim, Byung-Kwon</au><au>Kim, Sang Youl</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of regiocontrolled triarylamine-based polymer with a naphthol unit</atitle><jtitle>Polymer bulletin (Berlin, Germany)</jtitle><stitle>Polym. Bull</stitle><date>2021-02-01</date><risdate>2021</risdate><volume>78</volume><issue>2</issue><spage>965</spage><epage>979</epage><pages>965-979</pages><issn>0170-0839</issn><eissn>1436-2449</eissn><abstract>Redox-active polytriarylamine with hydroxyl groups is a useful material for optoelectronic applications, especially in the solution-processable multilayer devices. A novel regiocontrolled triarylamine-based polymer, poly(di-5-naphthyl-2-ol)phenylamine, with 2-naphthol units was synthesized via oxidative coupling polymerization. Polymerization in tetrahydrofuran using a Cu-amine complex oxidant under O
2
atmosphere produced polymers with number-averaged molecular weights as high as 11,300 g mol
−1
. The structure of the polymer was characterized by
1
H and
13
C NMR spectroscopy, showing that the oxidative coupling polymerization occurred at the outer
ortho
position of the 2-naphthols, preserving the hydroxyl groups. The polymer exhibited good solubility in polar aprotic solvents, with a high thermal stability of 446 °C that corresponded to 5% weight loss. The UV–vis absorption of the polymer was similar to that of DNPA, indicating that the kinked-structured polymer hindered the formation of charge-transfer complexes. These results suggest promising applications of the developed polymer in optoelectronic devices.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s00289-020-03146-y</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0003-4106-1996</orcidid></addata></record> |
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| subjects | Characterization and Evaluation of Materials Charge transfer Chemical synthesis Chemistry Chemistry and Materials Science Chromatography Complex Fluids and Microfluidics Electrodes Fourier transforms Hydroxyl groups Mechanical properties Molecular weight Multilayers Naphthol Nitrogen NMR spectroscopy Optoelectronic devices Organic Chemistry Original Paper Oxidizing agents Physical Chemistry Polymer Sciences Polymerization Polymers Soft and Granular Matter Solvents Tetrahydrofuran Thermal stability Weight loss |
| title | Synthesis of regiocontrolled triarylamine-based polymer with a naphthol unit |
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