Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange
Poly(3-hexylthiophene) (P3HT) is one of the most extensively investigated conjugated polymers and has been employed as the active material in many devices including field-effect transistors, organic photovoltaics and sensors. As a result, methods to further tune the properties of P3HT are desirable...
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| Formatua: | Artikulua |
| Hizkuntza: | en_US |
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American Chemical Society (ACS)
2017
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| Sarrera elektronikoa: | http://hdl.handle.net/1721.1/110415 https://orcid.org/0000-0003-0681-8084 |
| _version_ | 1826199790130561024 |
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| author | Koo, Byungjin Sletten, Ellen M. Swager, Timothy M |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Koo, Byungjin Sletten, Ellen M. Swager, Timothy M |
| author_sort | Koo, Byungjin |
| collection | MIT |
| description | Poly(3-hexylthiophene) (P3HT) is one of the most extensively investigated conjugated polymers and has been employed as the active material in many devices including field-effect transistors, organic photovoltaics and sensors. As a result, methods to further tune the properties of P3HT are desirable for specific applications. Herein, we report a facile postpolymerization modification strategy to functionalize the 4-position of commercially available P3HT in two simple steps–bromination of the 4-position of P3HT (Br–P3HT) followed by lithium−bromine exchange and quenching with an electrophile. We achieved near quantitative lithium–bromine exchange with Br–P3HT, which requires over 100 thienyl lithiates to be present on a single polymer chain. The lithiated-P3HT is readily combined with functional electrophiles, resulting in P3HT derivatives with ketones, secondary alcohols, trimethylsilyl (TMS) group, fluorine, or an azide at the 4-position. We demonstrated that the azide-modified P3HT could undergo Cu-catalyzed or Cu-free click chemistry, significantly expanding the complexity of the structures that can be appended to P3HT using this method. |
| first_indexed | 2024-09-23T11:25:49Z |
| format | Article |
| id | mit-1721.1/110415 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T11:25:49Z |
| publishDate | 2017 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1104152022-09-27T19:28:20Z Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange Koo, Byungjin Sletten, Ellen M. Swager, Timothy M Massachusetts Institute of Technology. Department of Chemistry Massachusetts Institute of Technology. Department of Materials Science and Engineering Koo, Byungjin Sletten, Ellen M. Swager, Timothy M Poly(3-hexylthiophene) (P3HT) is one of the most extensively investigated conjugated polymers and has been employed as the active material in many devices including field-effect transistors, organic photovoltaics and sensors. As a result, methods to further tune the properties of P3HT are desirable for specific applications. Herein, we report a facile postpolymerization modification strategy to functionalize the 4-position of commercially available P3HT in two simple steps–bromination of the 4-position of P3HT (Br–P3HT) followed by lithium−bromine exchange and quenching with an electrophile. We achieved near quantitative lithium–bromine exchange with Br–P3HT, which requires over 100 thienyl lithiates to be present on a single polymer chain. The lithiated-P3HT is readily combined with functional electrophiles, resulting in P3HT derivatives with ketones, secondary alcohols, trimethylsilyl (TMS) group, fluorine, or an azide at the 4-position. We demonstrated that the azide-modified P3HT could undergo Cu-catalyzed or Cu-free click chemistry, significantly expanding the complexity of the structures that can be appended to P3HT using this method. National Science Foundation (U.S.) (ECCS-0939514) 2017-07-03T13:13:55Z 2017-07-03T13:13:55Z 2014-12 2014-09 Article http://purl.org/eprint/type/JournalArticle 0024-9297 1520-5835 http://hdl.handle.net/1721.1/110415 Koo, Byungjin; Sletten, Ellen M. and Swager, Timothy M. "Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange." Macromolecules 48, 1 (December 2014): 229–235 © 2014 American Chemical Society https://orcid.org/0000-0003-0681-8084 en_US http://dx.doi.org/10.1021/ma5019044 Macromolecules Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) ACS |
| spellingShingle | Koo, Byungjin Sletten, Ellen M. Swager, Timothy M Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange |
| title | Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange |
| title_full | Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange |
| title_fullStr | Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange |
| title_full_unstemmed | Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange |
| title_short | Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange |
| title_sort | functionalized poly 3 hexylthiophene s via lithium bromine exchange |
| url | http://hdl.handle.net/1721.1/110415 https://orcid.org/0000-0003-0681-8084 |
| work_keys_str_mv | AT koobyungjin functionalizedpoly3hexylthiophenesvialithiumbromineexchange AT slettenellenm functionalizedpoly3hexylthiophenesvialithiumbromineexchange AT swagertimothym functionalizedpoly3hexylthiophenesvialithiumbromineexchange |