Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization
Conventional atom transfer radical polymerization (ATRP) involving metal/ligand complexes as the catalysts has been widely used for synthesis of myriads of polymers with controllable molecular weights, monomer sequences and chain end groups, but suffers from the metal-contamination in the final poly...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2021
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| Online Access: | https://hdl.handle.net/10356/152826 |
| _version_ | 1824454277279514624 |
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| author | Jia, Tao Huang, Shuo Bohra, Hassan Wang, Mingfeng |
| author2 | School of Chemical and Biomedical Engineering |
| author_facet | School of Chemical and Biomedical Engineering Jia, Tao Huang, Shuo Bohra, Hassan Wang, Mingfeng |
| author_sort | Jia, Tao |
| collection | NTU |
| description | Conventional atom transfer radical polymerization (ATRP) involving metal/ligand complexes as the catalysts has been widely used for synthesis of myriads of polymers with controllable molecular weights, monomer sequences and chain end groups, but suffers from the metal-contamination in the final polymer products. This issue has been recently mediated to some extent by using organic photocatalysts, which not only enable controllable polymerization upon light irradiation, but also offers spatiotemporal control of the polymerizations. To date the majority of reported organic photocatalysts for ATRP mainly absorb light in the UV region. Here we examined three organic chromophores, quinacridone, diketopyrrolopyrrole and indigo, as visible-light-absorbing organic photocatalysts for controllable polymerization of a series of methacrylates monomers via a scheme of light-mediated ATRP. Among the three types of organic chromophores, N,N-bis(tert-butyloxycarbonyl) quinacridone shows the highest fluorescence quantum yield and the best electrochemical and optical stability, all of which contribute to its outstanding performance in controllable polymerization of methacrylates under visible LED light irradiation. |
| first_indexed | 2025-02-19T03:19:45Z |
| format | Journal Article |
| id | ntu-10356/152826 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-02-19T03:19:45Z |
| publishDate | 2021 |
| record_format | dspace |
| spelling | ntu-10356/1528262021-10-05T08:36:22Z Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization Jia, Tao Huang, Shuo Bohra, Hassan Wang, Mingfeng School of Chemical and Biomedical Engineering Engineering::Bioengineering Dyes Photocatalyst Conventional atom transfer radical polymerization (ATRP) involving metal/ligand complexes as the catalysts has been widely used for synthesis of myriads of polymers with controllable molecular weights, monomer sequences and chain end groups, but suffers from the metal-contamination in the final polymer products. This issue has been recently mediated to some extent by using organic photocatalysts, which not only enable controllable polymerization upon light irradiation, but also offers spatiotemporal control of the polymerizations. To date the majority of reported organic photocatalysts for ATRP mainly absorb light in the UV region. Here we examined three organic chromophores, quinacridone, diketopyrrolopyrrole and indigo, as visible-light-absorbing organic photocatalysts for controllable polymerization of a series of methacrylates monomers via a scheme of light-mediated ATRP. Among the three types of organic chromophores, N,N-bis(tert-butyloxycarbonyl) quinacridone shows the highest fluorescence quantum yield and the best electrochemical and optical stability, all of which contribute to its outstanding performance in controllable polymerization of methacrylates under visible LED light irradiation. Ministry of Education (MOE) M.W. is grateful for the funding support through a start-up grant (M4080992.120) of Nanyang Assistant Professorship from the Nanyang Technological University and AcRF Tier 1 (RG 20/16, M4011620.120) from the Ministry of Education - Singapore. C.Y. and S.H. gratefully acknowledge the Ph.D. research scholarships from Nanyang Technological University. 2021-10-05T08:36:22Z 2021-10-05T08:36:22Z 2019 Journal Article Jia, T., Huang, S., Bohra, H. & Wang, M. (2019). Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization. Dyes and Pigments, 165, 223-230. https://dx.doi.org/10.1016/j.dyepig.2019.01.060 0143-7208 https://hdl.handle.net/10356/152826 10.1016/j.dyepig.2019.01.060 2-s2.0-85061895831 165 223 230 en M4080992.120 M4011620.120 Dyes and Pigments © 2019 Elsevier Ltd. All rights reserved. |
| spellingShingle | Engineering::Bioengineering Dyes Photocatalyst Jia, Tao Huang, Shuo Bohra, Hassan Wang, Mingfeng Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization |
| title | Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization |
| title_full | Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization |
| title_fullStr | Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization |
| title_full_unstemmed | Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization |
| title_short | Examining derivatives of quinacridone, diketopyrrolopyrrole and indigo as the visible-light organic photocatalysts for metal-free atom transfer radical polymerization |
| title_sort | examining derivatives of quinacridone diketopyrrolopyrrole and indigo as the visible light organic photocatalysts for metal free atom transfer radical polymerization |
| topic | Engineering::Bioengineering Dyes Photocatalyst |
| url | https://hdl.handle.net/10356/152826 |
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