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环丁烯二酮-联噻吩π共轭聚合物的合成与表征：芳基溴化物与格氏试剂之间 Kumada-Tamao-Corriu 偶联聚合的缩醛保护策略

Synthesis and characterization of cyclobutenedione-bithiophene π-conjugated polymers: acetal-protecting strategy for Kumada-Tamao-Corriu coupling polymerization between aryl bromide and Grignard reagents.

作者信息

Ohishi Tomoyuki, Sone Takuma, Oda Kohei, Yokoyama Akihiro

机构信息

Department of Materials and Life Science, Faculty of Science and Technology, Seikei University 3-3-1 Kichijoji-Kitamachi Musashino Tokyo 180-8633 Japan

出版信息

RSC Adv. 2019 Dec 11;9(70):40863-40872. doi: 10.1039/c9ra08275a. eCollection 2019 Dec 9.

DOI:10.1039/c9ra08275a
PMID:35540031
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9076255/
Abstract

Cyclobutenedione is an aromatic ring that exhibits strong electron-withdrawing properties but is susceptible to undesired reactions with nucleophiles. Herein, Kumada-Tamao-Corriu coupling polymerization of a cyclobutenedione monomer whose carbonyl groups are protected as acetals was achieved. Hydrolysis of the acetals afforded donor-acceptor type π-conjugated polymers consisting of cyclobutenedione as an acceptor unit and bithiophene as a donor unit. The acetal-protected monomer was also subjected to Suzuki-Miyaura coupling polymerization. The absorption and emission spectra of the deprotected polymers shifted to the longer wavelength compared with the acetal-protected polymers.

摘要

环丁二酮是一种具有强吸电子性质的芳香环，但易与亲核试剂发生不期望的反应。在此，实现了羰基被保护为缩醛的环丁二酮单体的熊田-玉尾-古里偶联聚合反应。缩醛水解得到由环丁二酮作为受体单元和联噻吩作为供体单元组成的供体-受体型π共轭聚合物。该缩醛保护的单体也进行了铃木-宫浦偶联聚合反应。与缩醛保护的聚合物相比，脱保护聚合物的吸收光谱和发射光谱向更长波长移动。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/aa4119597540/c9ra08275a-f4.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/8cf4ac7dd332/c9ra08275a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/59f27268297b/c9ra08275a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/3c856602f011/c9ra08275a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/24bd7acb3788/c9ra08275a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/1a415a438f0d/c9ra08275a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/aa4119597540/c9ra08275a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/e319429488db/c9ra08275a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/0dcc433584ca/c9ra08275a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/72633d4d7193/c9ra08275a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/8cf4ac7dd332/c9ra08275a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/59f27268297b/c9ra08275a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/3c856602f011/c9ra08275a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/24bd7acb3788/c9ra08275a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/1a415a438f0d/c9ra08275a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d0a0/9076255/aa4119597540/c9ra08275a-f4.jpg

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