Donor-Acceptor-Type Copolymers Based on 3,4-Propylenedioxy-thiophene and 5,6-Difluorobenzotriazole: Synthesis and Electrochromic Properties
Three solution-processable D-A-type conjugated polymers , and were successfully synthesized via the Pd-catalyzed Stille cross-coupling copolymerization approach, with 6,8-Dibromo-3,3-bis-decyl-3,4-dihydro-2 -thieno[3,4- ][1,4] dioxepine (M1) and 2,5-Bis(trimethylstannanyl)thiophene (M3) as the donor...
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| Veröffentlicht in: | Polymers 2018-04, Vol.10 (4), p.427 |
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| creator | Feng, Fanda Kong, Lingqian Du, Hongmei Zhao, Jinsheng Zhang, Junhong |
| description | Three solution-processable D-A-type conjugated polymers
,
and
were successfully synthesized via the Pd-catalyzed Stille cross-coupling copolymerization approach, with 6,8-Dibromo-3,3-bis-decyl-3,4-dihydro-2
-thieno[3,4-
][1,4] dioxepine (M1) and 2,5-Bis(trimethylstannanyl)thiophene (M3) as the donor units and 4,7-Dibromo-5,6-difluoro-2-(2-hexyl-decyl)-2
-benzotriazole (M2) as the acceptor unit, wherein the feed ratio of the three units was 1:3:4 (M1:M2:M3, the same below), 1:1:2 and 3:1:4 for
,
, and
, respectively. The results obtained by our test showed that the feed ratio between the D and A units had a significant effect on both the electrochemical and the spectroelectrochemical properties of the three polymers. The copolymers exhibited a gradually deepening red color in neutral state with the increase of M1 content and then turned to a transmissive grey color in the oxidation state. Also, three copolymers showed good performance in electrochromic parameters, which mainly consists of optical contrast, response time, and coloration efficiency. In general, the excellent electrochromic performances of the copolymers make them outstanding candidates for electrochromic material applications. |
| doi_str_mv | 10.3390/polym10040427 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_6415233</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2207157692</sourcerecordid><originalsourceid>FETCH-LOGICAL-c415t-c20317151b1dcd97e597c89bc0b5861017de719829505f09f78541c61b7271603</originalsourceid><addsrcrecordid>eNpdkctu1jAQRiNERau2S7YoEhsWDfgS279ZIJW_5SJVAomythJnQlwlnmA7qOkr9KVxL1Qt3ngsH53x-CuKl5S85VyTdzOO60QJqUnN1LNijxHFq5pL8vxRvVscxnhB8qqFlFS9KHY50VLWku0V1yfoMVTH1sKccnG-zlBu8VYMIZYfmwhdib7kR3X1PeC8juChc3i5VmlwOA_5WDa-K8WRrE5cPy4YsAV_hSm45gpHeF_-WH0aILp4C56OYFNAOwScnC1vpBCSg3hQ7PTNGOHwft8vfn46Pd9-qc6-ff66PT6rbE1FqiwjnCoqaEs722kFQiu70a0lrdhISqjqQFG9YVoQ0RPdq42oqZW0VUxRSfh-8eHOOy_tBJ0Fn0Izmjm4qQmrwcaZpzfeDeYX_jEy92ecZ8Gbe0HA3wvEZCYXLYxj4wGXaFj-eyqU1Cyjr_9DL3AJPo9nWI5NCUm0ylR1R9mAMQboHx5DiblJ2jxJOvOvHk_wQP_Llf8F1CSmHQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2040756097</pqid></control><display><type>article</type><title>Donor-Acceptor-Type Copolymers Based on 3,4-Propylenedioxy-thiophene and 5,6-Difluorobenzotriazole: Synthesis and Electrochromic Properties</title><source>MDPI - Multidisciplinary Digital Publishing Institute</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central</source><source>PubMed Central Open Access</source><creator>Feng, Fanda ; Kong, Lingqian ; Du, Hongmei ; Zhao, Jinsheng ; Zhang, Junhong</creator><creatorcontrib>Feng, Fanda ; Kong, Lingqian ; Du, Hongmei ; Zhao, Jinsheng ; Zhang, Junhong</creatorcontrib><description>Three solution-processable D-A-type conjugated polymers
,
and
were successfully synthesized via the Pd-catalyzed Stille cross-coupling copolymerization approach, with 6,8-Dibromo-3,3-bis-decyl-3,4-dihydro-2
-thieno[3,4-
][1,4] dioxepine (M1) and 2,5-Bis(trimethylstannanyl)thiophene (M3) as the donor units and 4,7-Dibromo-5,6-difluoro-2-(2-hexyl-decyl)-2
-benzotriazole (M2) as the acceptor unit, wherein the feed ratio of the three units was 1:3:4 (M1:M2:M3, the same below), 1:1:2 and 3:1:4 for
,
, and
, respectively. The results obtained by our test showed that the feed ratio between the D and A units had a significant effect on both the electrochemical and the spectroelectrochemical properties of the three polymers. The copolymers exhibited a gradually deepening red color in neutral state with the increase of M1 content and then turned to a transmissive grey color in the oxidation state. Also, three copolymers showed good performance in electrochromic parameters, which mainly consists of optical contrast, response time, and coloration efficiency. In general, the excellent electrochromic performances of the copolymers make them outstanding candidates for electrochromic material applications.</description><identifier>ISSN: 2073-4360</identifier><identifier>EISSN: 2073-4360</identifier><identifier>DOI: 10.3390/polym10040427</identifier><identifier>PMID: 30966462</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Benzotriazole ; Chemical synthesis ; Copolymerization ; Copolymers ; Cross coupling ; Electrochromism ; Oxidation ; Polymers ; Response time ; Valence</subject><ispartof>Polymers, 2018-04, Vol.10 (4), p.427</ispartof><rights>Copyright MDPI AG 2018</rights><rights>2018 by the authors. 2018</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-c20317151b1dcd97e597c89bc0b5861017de719829505f09f78541c61b7271603</citedby><cites>FETCH-LOGICAL-c415t-c20317151b1dcd97e597c89bc0b5861017de719829505f09f78541c61b7271603</cites><orcidid>0000-0002-1576-7971</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6415233/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6415233/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30966462$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Feng, Fanda</creatorcontrib><creatorcontrib>Kong, Lingqian</creatorcontrib><creatorcontrib>Du, Hongmei</creatorcontrib><creatorcontrib>Zhao, Jinsheng</creatorcontrib><creatorcontrib>Zhang, Junhong</creatorcontrib><title>Donor-Acceptor-Type Copolymers Based on 3,4-Propylenedioxy-thiophene and 5,6-Difluorobenzotriazole: Synthesis and Electrochromic Properties</title><title>Polymers</title><addtitle>Polymers (Basel)</addtitle><description>Three solution-processable D-A-type conjugated polymers
,
and
were successfully synthesized via the Pd-catalyzed Stille cross-coupling copolymerization approach, with 6,8-Dibromo-3,3-bis-decyl-3,4-dihydro-2
-thieno[3,4-
][1,4] dioxepine (M1) and 2,5-Bis(trimethylstannanyl)thiophene (M3) as the donor units and 4,7-Dibromo-5,6-difluoro-2-(2-hexyl-decyl)-2
-benzotriazole (M2) as the acceptor unit, wherein the feed ratio of the three units was 1:3:4 (M1:M2:M3, the same below), 1:1:2 and 3:1:4 for
,
, and
, respectively. The results obtained by our test showed that the feed ratio between the D and A units had a significant effect on both the electrochemical and the spectroelectrochemical properties of the three polymers. The copolymers exhibited a gradually deepening red color in neutral state with the increase of M1 content and then turned to a transmissive grey color in the oxidation state. Also, three copolymers showed good performance in electrochromic parameters, which mainly consists of optical contrast, response time, and coloration efficiency. In general, the excellent electrochromic performances of the copolymers make them outstanding candidates for electrochromic material applications.</description><subject>Benzotriazole</subject><subject>Chemical synthesis</subject><subject>Copolymerization</subject><subject>Copolymers</subject><subject>Cross coupling</subject><subject>Electrochromism</subject><subject>Oxidation</subject><subject>Polymers</subject><subject>Response time</subject><subject>Valence</subject><issn>2073-4360</issn><issn>2073-4360</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNpdkctu1jAQRiNERau2S7YoEhsWDfgS279ZIJW_5SJVAomythJnQlwlnmA7qOkr9KVxL1Qt3ngsH53x-CuKl5S85VyTdzOO60QJqUnN1LNijxHFq5pL8vxRvVscxnhB8qqFlFS9KHY50VLWku0V1yfoMVTH1sKccnG-zlBu8VYMIZYfmwhdib7kR3X1PeC8juChc3i5VmlwOA_5WDa-K8WRrE5cPy4YsAV_hSm45gpHeF_-WH0aILp4C56OYFNAOwScnC1vpBCSg3hQ7PTNGOHwft8vfn46Pd9-qc6-ff66PT6rbE1FqiwjnCoqaEs722kFQiu70a0lrdhISqjqQFG9YVoQ0RPdq42oqZW0VUxRSfh-8eHOOy_tBJ0Fn0Izmjm4qQmrwcaZpzfeDeYX_jEy92ecZ8Gbe0HA3wvEZCYXLYxj4wGXaFj-eyqU1Cyjr_9DL3AJPo9nWI5NCUm0ylR1R9mAMQboHx5DiblJ2jxJOvOvHk_wQP_Llf8F1CSmHQ</recordid><startdate>20180411</startdate><enddate>20180411</enddate><creator>Feng, Fanda</creator><creator>Kong, Lingqian</creator><creator>Du, Hongmei</creator><creator>Zhao, Jinsheng</creator><creator>Zhang, Junhong</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</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>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-1576-7971</orcidid></search><sort><creationdate>20180411</creationdate><title>Donor-Acceptor-Type Copolymers Based on 3,4-Propylenedioxy-thiophene and 5,6-Difluorobenzotriazole: Synthesis and Electrochromic Properties</title><author>Feng, Fanda ; Kong, Lingqian ; Du, Hongmei ; Zhao, Jinsheng ; Zhang, Junhong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-c20317151b1dcd97e597c89bc0b5861017de719829505f09f78541c61b7271603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Benzotriazole</topic><topic>Chemical synthesis</topic><topic>Copolymerization</topic><topic>Copolymers</topic><topic>Cross coupling</topic><topic>Electrochromism</topic><topic>Oxidation</topic><topic>Polymers</topic><topic>Response time</topic><topic>Valence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Feng, Fanda</creatorcontrib><creatorcontrib>Kong, Lingqian</creatorcontrib><creatorcontrib>Du, Hongmei</creatorcontrib><creatorcontrib>Zhao, Jinsheng</creatorcontrib><creatorcontrib>Zhang, Junhong</creatorcontrib><collection>PubMed</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 (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</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>Publicly Available Content Database</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>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Feng, Fanda</au><au>Kong, Lingqian</au><au>Du, Hongmei</au><au>Zhao, Jinsheng</au><au>Zhang, Junhong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Donor-Acceptor-Type Copolymers Based on 3,4-Propylenedioxy-thiophene and 5,6-Difluorobenzotriazole: Synthesis and Electrochromic Properties</atitle><jtitle>Polymers</jtitle><addtitle>Polymers (Basel)</addtitle><date>2018-04-11</date><risdate>2018</risdate><volume>10</volume><issue>4</issue><spage>427</spage><pages>427-</pages><issn>2073-4360</issn><eissn>2073-4360</eissn><abstract>Three solution-processable D-A-type conjugated polymers
,
and
were successfully synthesized via the Pd-catalyzed Stille cross-coupling copolymerization approach, with 6,8-Dibromo-3,3-bis-decyl-3,4-dihydro-2
-thieno[3,4-
][1,4] dioxepine (M1) and 2,5-Bis(trimethylstannanyl)thiophene (M3) as the donor units and 4,7-Dibromo-5,6-difluoro-2-(2-hexyl-decyl)-2
-benzotriazole (M2) as the acceptor unit, wherein the feed ratio of the three units was 1:3:4 (M1:M2:M3, the same below), 1:1:2 and 3:1:4 for
,
, and
, respectively. The results obtained by our test showed that the feed ratio between the D and A units had a significant effect on both the electrochemical and the spectroelectrochemical properties of the three polymers. The copolymers exhibited a gradually deepening red color in neutral state with the increase of M1 content and then turned to a transmissive grey color in the oxidation state. Also, three copolymers showed good performance in electrochromic parameters, which mainly consists of optical contrast, response time, and coloration efficiency. In general, the excellent electrochromic performances of the copolymers make them outstanding candidates for electrochromic material applications.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>30966462</pmid><doi>10.3390/polym10040427</doi><orcidid>https://orcid.org/0000-0002-1576-7971</orcidid><oa>free_for_read</oa></addata></record> |
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| source | MDPI - Multidisciplinary Digital Publishing Institute; EZB-FREE-00999 freely available EZB journals; PubMed Central; PubMed Central Open Access |
| subjects | Benzotriazole Chemical synthesis Copolymerization Copolymers Cross coupling Electrochromism Oxidation Polymers Response time Valence |
| title | Donor-Acceptor-Type Copolymers Based on 3,4-Propylenedioxy-thiophene and 5,6-Difluorobenzotriazole: Synthesis and Electrochromic Properties |
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