Rhodanine-based Knoevenagel reaction and ring-opening polymerization for efficiently constructing multicyclic polymers

Ze Zhang, Xuan Nie, Fei Wang, Guang Chen, Wei-Qiang Huang, Lei Xia, Wen-Jian Zhang, Zong-Yao Hao (), Chun-Yan Hong (), Long-Hai Wang () and Ye-Zi You ()
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Ze Zhang: University of Science and Technology of China
Xuan Nie: University of Science and Technology of China
Fei Wang: The First Affiliated Hospital of University of Science and Technology of China
Guang Chen: University of Science and Technology of China
Wei-Qiang Huang: University of Science and Technology of China
Lei Xia: University of Science and Technology of China
Wen-Jian Zhang: University of Science and Technology of China
Zong-Yao Hao: The First Affiliated Hospital of Anhui Medical University and Institute of Urology, Anhui Medical University
Chun-Yan Hong: University of Science and Technology of China
Long-Hai Wang: University of Science and Technology of China
Ye-Zi You: University of Science and Technology of China

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five˗membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine˗based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers.

Date: 2020
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DOI: 10.1038/s41467-020-17474-0

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