An efficient lactone-to-lactam conversion for the synthesis of thiophene Pechmann lactam and the characterization of polymers thereof
Despite having unique structural features, e.g. , high co-planarity and a strong polar bicyclic lactam structure, thiophene bipyrrolylidene-2,2′(1 H ,1′ H )-dione (TBPD) has been less explored as a dye, mainly due to the quite low yield in its synthesis via lactone-to-lactam conversion. We reported...
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| Veröffentlicht in: | Polymer chemistry 2018-11, Vol.9 (42), p.5234-5241 |
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| container_title | Polymer chemistry |
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| creator | Lee, Kyu Cheol Lee, Hae Rang Kang, So-Huei Lee, Jungho Park, Young IL Noh, Seung Man Oh, Joon Hak Yang, Changduk |
| description | Despite having unique structural features,
e.g.
, high co-planarity and a strong polar bicyclic lactam structure, thiophene bipyrrolylidene-2,2′(1
H
,1′
H
)-dione (TBPD) has been less explored as a dye, mainly due to the quite low yield in its synthesis
via
lactone-to-lactam conversion. We reported an efficient methodology for synthesizing TBPD in high yield using
p
-toluenesulfonic acid monohydrate and a catalytic amount of 4-dimethylaminopyridine in the chloroform solvent. From the newly synthesized series of TBPD-based donor–acceptor-type polymers, we fabricated organic field-effect transistors (OFETs), which were subjected to a systematic study on the relationship between film microstructure and charge transport. Among them, the annealed PTBPD-Th film revealed a more ordered lamellar packing with the highest number of interlayers and preferential edge-on orientation, yielding the best hole mobility (up to 0.46 cm
2
V
−1
s
−1
). The improved synthesis of TBPD and our findings concerning related polymers could promote further research and development associated with the TBPD unit. |
| doi_str_mv | 10.1039/C8PY00997J |
| format | Article |
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e.g.
, high co-planarity and a strong polar bicyclic lactam structure, thiophene bipyrrolylidene-2,2′(1
H
,1′
H
)-dione (TBPD) has been less explored as a dye, mainly due to the quite low yield in its synthesis
via
lactone-to-lactam conversion. We reported an efficient methodology for synthesizing TBPD in high yield using
p
-toluenesulfonic acid monohydrate and a catalytic amount of 4-dimethylaminopyridine in the chloroform solvent. From the newly synthesized series of TBPD-based donor–acceptor-type polymers, we fabricated organic field-effect transistors (OFETs), which were subjected to a systematic study on the relationship between film microstructure and charge transport. Among them, the annealed PTBPD-Th film revealed a more ordered lamellar packing with the highest number of interlayers and preferential edge-on orientation, yielding the best hole mobility (up to 0.46 cm
2
V
−1
s
−1
). The improved synthesis of TBPD and our findings concerning related polymers could promote further research and development associated with the TBPD unit.</description><identifier>ISSN: 1759-9954</identifier><identifier>EISSN: 1759-9962</identifier><identifier>DOI: 10.1039/C8PY00997J</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Amides ; Catalysis ; Charge transport ; Chemical synthesis ; Chloroform ; Conversion ; Field effect transistors ; Hole mobility ; Interlayers ; Polymer chemistry ; Polymers ; R&D ; Research & development ; Semiconductor devices</subject><ispartof>Polymer chemistry, 2018-11, Vol.9 (42), p.5234-5241</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c325t-5bf0feba36ba18c9221b4a60609e0dea2581a18ab1e708efd437fc4c827373db3</citedby><cites>FETCH-LOGICAL-c325t-5bf0feba36ba18c9221b4a60609e0dea2581a18ab1e708efd437fc4c827373db3</cites><orcidid>0000-0001-6052-7451 ; 0000-0003-0481-6069 ; 0000-0002-0977-6265</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Lee, Kyu Cheol</creatorcontrib><creatorcontrib>Lee, Hae Rang</creatorcontrib><creatorcontrib>Kang, So-Huei</creatorcontrib><creatorcontrib>Lee, Jungho</creatorcontrib><creatorcontrib>Park, Young IL</creatorcontrib><creatorcontrib>Noh, Seung Man</creatorcontrib><creatorcontrib>Oh, Joon Hak</creatorcontrib><creatorcontrib>Yang, Changduk</creatorcontrib><title>An efficient lactone-to-lactam conversion for the synthesis of thiophene Pechmann lactam and the characterization of polymers thereof</title><title>Polymer chemistry</title><description>Despite having unique structural features,
e.g.
, high co-planarity and a strong polar bicyclic lactam structure, thiophene bipyrrolylidene-2,2′(1
H
,1′
H
)-dione (TBPD) has been less explored as a dye, mainly due to the quite low yield in its synthesis
via
lactone-to-lactam conversion. We reported an efficient methodology for synthesizing TBPD in high yield using
p
-toluenesulfonic acid monohydrate and a catalytic amount of 4-dimethylaminopyridine in the chloroform solvent. From the newly synthesized series of TBPD-based donor–acceptor-type polymers, we fabricated organic field-effect transistors (OFETs), which were subjected to a systematic study on the relationship between film microstructure and charge transport. Among them, the annealed PTBPD-Th film revealed a more ordered lamellar packing with the highest number of interlayers and preferential edge-on orientation, yielding the best hole mobility (up to 0.46 cm
2
V
−1
s
−1
). The improved synthesis of TBPD and our findings concerning related polymers could promote further research and development associated with the TBPD unit.</description><subject>Amides</subject><subject>Catalysis</subject><subject>Charge transport</subject><subject>Chemical synthesis</subject><subject>Chloroform</subject><subject>Conversion</subject><subject>Field effect transistors</subject><subject>Hole mobility</subject><subject>Interlayers</subject><subject>Polymer chemistry</subject><subject>Polymers</subject><subject>R&D</subject><subject>Research & development</subject><subject>Semiconductor devices</subject><issn>1759-9954</issn><issn>1759-9962</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpFUE1LAzEUDKJgqb34CwLehNV87FeOpfhJwR704GnJZl_YlN1kTbZCvfu_zdqi7zKPeTPzYBC6pOSGEi5uV-XmnRAhiucTNKNFJhIhcnb6t2fpOVqEsCVxOE0Zz2foe2kxaG2UATviTqrRWUhGl0yr7LFy9hN8MM5i7TweW8BhbyMEE7DTkTBuaMEC3oBqe2ktPjqlbX7lqpU-MuDNlxynnOgaXLfvY-wk8OD0BTrTsguwOOIcvd3fva4ek_XLw9NquU4UZ9mYZLUmGmrJ81rSUgnGaJ3KnOREAGlAsqyk8SBrCgUpQTcpL7RKVckKXvCm5nN0dcgdvPvYQRirrdt5G19WjLI81sUZjarrg0p5F4IHXQ3e9NLvK0qqqenqv2n-A-vnc2s</recordid><startdate>20181114</startdate><enddate>20181114</enddate><creator>Lee, Kyu Cheol</creator><creator>Lee, Hae Rang</creator><creator>Kang, So-Huei</creator><creator>Lee, Jungho</creator><creator>Park, Young IL</creator><creator>Noh, Seung Man</creator><creator>Oh, Joon Hak</creator><creator>Yang, Changduk</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-6052-7451</orcidid><orcidid>https://orcid.org/0000-0003-0481-6069</orcidid><orcidid>https://orcid.org/0000-0002-0977-6265</orcidid></search><sort><creationdate>20181114</creationdate><title>An efficient lactone-to-lactam conversion for the synthesis of thiophene Pechmann lactam and the characterization of polymers thereof</title><author>Lee, Kyu Cheol ; Lee, Hae Rang ; Kang, So-Huei ; Lee, Jungho ; Park, Young IL ; Noh, Seung Man ; Oh, Joon Hak ; Yang, Changduk</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-5bf0feba36ba18c9221b4a60609e0dea2581a18ab1e708efd437fc4c827373db3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Amides</topic><topic>Catalysis</topic><topic>Charge transport</topic><topic>Chemical synthesis</topic><topic>Chloroform</topic><topic>Conversion</topic><topic>Field effect transistors</topic><topic>Hole mobility</topic><topic>Interlayers</topic><topic>Polymer chemistry</topic><topic>Polymers</topic><topic>R&D</topic><topic>Research & development</topic><topic>Semiconductor devices</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Kyu Cheol</creatorcontrib><creatorcontrib>Lee, Hae Rang</creatorcontrib><creatorcontrib>Kang, So-Huei</creatorcontrib><creatorcontrib>Lee, Jungho</creatorcontrib><creatorcontrib>Park, Young IL</creatorcontrib><creatorcontrib>Noh, Seung Man</creatorcontrib><creatorcontrib>Oh, Joon Hak</creatorcontrib><creatorcontrib>Yang, Changduk</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Polymer chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Kyu Cheol</au><au>Lee, Hae Rang</au><au>Kang, So-Huei</au><au>Lee, Jungho</au><au>Park, Young IL</au><au>Noh, Seung Man</au><au>Oh, Joon Hak</au><au>Yang, Changduk</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An efficient lactone-to-lactam conversion for the synthesis of thiophene Pechmann lactam and the characterization of polymers thereof</atitle><jtitle>Polymer chemistry</jtitle><date>2018-11-14</date><risdate>2018</risdate><volume>9</volume><issue>42</issue><spage>5234</spage><epage>5241</epage><pages>5234-5241</pages><issn>1759-9954</issn><eissn>1759-9962</eissn><abstract>Despite having unique structural features,
e.g.
, high co-planarity and a strong polar bicyclic lactam structure, thiophene bipyrrolylidene-2,2′(1
H
,1′
H
)-dione (TBPD) has been less explored as a dye, mainly due to the quite low yield in its synthesis
via
lactone-to-lactam conversion. We reported an efficient methodology for synthesizing TBPD in high yield using
p
-toluenesulfonic acid monohydrate and a catalytic amount of 4-dimethylaminopyridine in the chloroform solvent. From the newly synthesized series of TBPD-based donor–acceptor-type polymers, we fabricated organic field-effect transistors (OFETs), which were subjected to a systematic study on the relationship between film microstructure and charge transport. Among them, the annealed PTBPD-Th film revealed a more ordered lamellar packing with the highest number of interlayers and preferential edge-on orientation, yielding the best hole mobility (up to 0.46 cm
2
V
−1
s
−1
). The improved synthesis of TBPD and our findings concerning related polymers could promote further research and development associated with the TBPD unit.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C8PY00997J</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-6052-7451</orcidid><orcidid>https://orcid.org/0000-0003-0481-6069</orcidid><orcidid>https://orcid.org/0000-0002-0977-6265</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1759-9954 |
| ispartof | Polymer chemistry, 2018-11, Vol.9 (42), p.5234-5241 |
| issn | 1759-9954 1759-9962 |
| language | eng |
| recordid | cdi_proquest_journals_2126996321 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Amides Catalysis Charge transport Chemical synthesis Chloroform Conversion Field effect transistors Hole mobility Interlayers Polymer chemistry Polymers R&D Research & development Semiconductor devices |
| title | An efficient lactone-to-lactam conversion for the synthesis of thiophene Pechmann lactam and the characterization of polymers thereof |
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