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Synthesis of Chain-End Functional Polydienes Using Diene Comonomer Bearing Boronic Acid Masked with Diaminonaphthalene
Diene comonomers bearing boronic acid masked with 1,8-diaminonaphthalene (dan) were applied to copolymerization with isoprene or butadiene using neodymium borohydride complex as a catalyst. The comonomers were tolerant to excess modified methylaluminoxane (MMAO) and thus were applicable to the polym...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9780943/ https://www.ncbi.nlm.nih.gov/pubmed/36558140 http://dx.doi.org/10.3390/molecules27249007 |
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author | Tanaka, Ryo Kuwabara, Yuina Nakayama, Yuushou Shiono, Takeshi |
author_facet | Tanaka, Ryo Kuwabara, Yuina Nakayama, Yuushou Shiono, Takeshi |
author_sort | Tanaka, Ryo |
collection | PubMed |
description | Diene comonomers bearing boronic acid masked with 1,8-diaminonaphthalene (dan) were applied to copolymerization with isoprene or butadiene using neodymium borohydride complex as a catalyst. The comonomers were tolerant to excess modified methylaluminoxane (MMAO) and thus were applicable to the polymerization system using MMAO. On the other hand, the corresponding pinacol borate was highly reactive toward MMAO, and no incorporation into the obtained polymer was observed. A (13)C NMR microstructural analysis of the hydrogenated copolymer revealed that all of the comonomers were located at the chain end. Further functionalization using the boron moiety at the polymer chain end was also investigated. |
format | Online Article Text |
id | pubmed-9780943 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-97809432022-12-24 Synthesis of Chain-End Functional Polydienes Using Diene Comonomer Bearing Boronic Acid Masked with Diaminonaphthalene Tanaka, Ryo Kuwabara, Yuina Nakayama, Yuushou Shiono, Takeshi Molecules Article Diene comonomers bearing boronic acid masked with 1,8-diaminonaphthalene (dan) were applied to copolymerization with isoprene or butadiene using neodymium borohydride complex as a catalyst. The comonomers were tolerant to excess modified methylaluminoxane (MMAO) and thus were applicable to the polymerization system using MMAO. On the other hand, the corresponding pinacol borate was highly reactive toward MMAO, and no incorporation into the obtained polymer was observed. A (13)C NMR microstructural analysis of the hydrogenated copolymer revealed that all of the comonomers were located at the chain end. Further functionalization using the boron moiety at the polymer chain end was also investigated. MDPI 2022-12-17 /pmc/articles/PMC9780943/ /pubmed/36558140 http://dx.doi.org/10.3390/molecules27249007 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Tanaka, Ryo Kuwabara, Yuina Nakayama, Yuushou Shiono, Takeshi Synthesis of Chain-End Functional Polydienes Using Diene Comonomer Bearing Boronic Acid Masked with Diaminonaphthalene |
title | Synthesis of Chain-End Functional Polydienes Using Diene Comonomer Bearing Boronic Acid Masked with Diaminonaphthalene |
title_full | Synthesis of Chain-End Functional Polydienes Using Diene Comonomer Bearing Boronic Acid Masked with Diaminonaphthalene |
title_fullStr | Synthesis of Chain-End Functional Polydienes Using Diene Comonomer Bearing Boronic Acid Masked with Diaminonaphthalene |
title_full_unstemmed | Synthesis of Chain-End Functional Polydienes Using Diene Comonomer Bearing Boronic Acid Masked with Diaminonaphthalene |
title_short | Synthesis of Chain-End Functional Polydienes Using Diene Comonomer Bearing Boronic Acid Masked with Diaminonaphthalene |
title_sort | synthesis of chain-end functional polydienes using diene comonomer bearing boronic acid masked with diaminonaphthalene |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9780943/ https://www.ncbi.nlm.nih.gov/pubmed/36558140 http://dx.doi.org/10.3390/molecules27249007 |
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