Copper-Catalyzed C(3+1) copolymerization of propargyl carbonates and aryldiazomethanes
Controlling the composition and sequence during diazo copolymerization with vinyl or acetylenic monomers is highly desired yet challenging. Here we report a new base-metal-catalysis strategy to address this problem via tandem coupling/polymerization. A selective Cu-catalyzed C(3+1) copolymerization...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-03-01
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| Series: | Giant |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666542523000012 |
| _version_ | 1827989181277667328 |
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| author | Hao-Ze Su Bin Wu Jianbo Wang Rong Zhu |
| author_facet | Hao-Ze Su Bin Wu Jianbo Wang Rong Zhu |
| author_sort | Hao-Ze Su |
| collection | DOAJ |
| description | Controlling the composition and sequence during diazo copolymerization with vinyl or acetylenic monomers is highly desired yet challenging. Here we report a new base-metal-catalysis strategy to address this problem via tandem coupling/polymerization. A selective Cu-catalyzed C(3+1) copolymerization reaction was developed using propargyl carbonates and aryldiazomethanes derived from N-tosylhydrazones as the C3 and C1 building blocks, respectively. This reaction rapidly produces alternating-like poly(1,4-diaryl-2-butyne-1,4-diyl)s (Mn up to 31.0 kg/mol) in a modular fashion, without detectable homopolymer segments. This work provides a new avenue for the synthesis of hydrocarbon polymers through diazo copolymerization. |
| first_indexed | 2024-04-10T00:15:18Z |
| format | Article |
| id | doaj.art-3ae6490a758f45cf8f1ce32f84834969 |
| institution | Directory Open Access Journal |
| issn | 2666-5425 |
| language | English |
| last_indexed | 2024-04-10T00:15:18Z |
| publishDate | 2023-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Giant |
| spelling | doaj.art-3ae6490a758f45cf8f1ce32f848349692023-03-16T05:06:21ZengElsevierGiant2666-54252023-03-0113100139Copper-Catalyzed C(3+1) copolymerization of propargyl carbonates and aryldiazomethanesHao-Ze Su0Bin Wu1Jianbo Wang2Rong Zhu3Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, ChinaBeijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, ChinaBeijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China; State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaBeijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China; Corresponding author.Controlling the composition and sequence during diazo copolymerization with vinyl or acetylenic monomers is highly desired yet challenging. Here we report a new base-metal-catalysis strategy to address this problem via tandem coupling/polymerization. A selective Cu-catalyzed C(3+1) copolymerization reaction was developed using propargyl carbonates and aryldiazomethanes derived from N-tosylhydrazones as the C3 and C1 building blocks, respectively. This reaction rapidly produces alternating-like poly(1,4-diaryl-2-butyne-1,4-diyl)s (Mn up to 31.0 kg/mol) in a modular fashion, without detectable homopolymer segments. This work provides a new avenue for the synthesis of hydrocarbon polymers through diazo copolymerization.http://www.sciencedirect.com/science/article/pii/S2666542523000012CopperDiazoChain-growth polymerizationHydrocarbon polymersAlkynes |
| spellingShingle | Hao-Ze Su Bin Wu Jianbo Wang Rong Zhu Copper-Catalyzed C(3+1) copolymerization of propargyl carbonates and aryldiazomethanes Giant Copper Diazo Chain-growth polymerization Hydrocarbon polymers Alkynes |
| title | Copper-Catalyzed C(3+1) copolymerization of propargyl carbonates and aryldiazomethanes |
| title_full | Copper-Catalyzed C(3+1) copolymerization of propargyl carbonates and aryldiazomethanes |
| title_fullStr | Copper-Catalyzed C(3+1) copolymerization of propargyl carbonates and aryldiazomethanes |
| title_full_unstemmed | Copper-Catalyzed C(3+1) copolymerization of propargyl carbonates and aryldiazomethanes |
| title_short | Copper-Catalyzed C(3+1) copolymerization of propargyl carbonates and aryldiazomethanes |
| title_sort | copper catalyzed c 3 1 copolymerization of propargyl carbonates and aryldiazomethanes |
| topic | Copper Diazo Chain-growth polymerization Hydrocarbon polymers Alkynes |
| url | http://www.sciencedirect.com/science/article/pii/S2666542523000012 |
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