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Issue 40, 2020
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A facile approach for preparing tadpole and barbell-shaped cyclic polymers through combining ATRP and atom transfer radical coupling (ATRC) reactions

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Abstract

The ring-forming behavior of polymers with an odd number of arms in highly dilute solutions has been studied using tri-arm polystyrene (PSt3) as a model through combining atom transfer radical polymerization (ATRP) and atom transfer radical coupling (ATRC) technologies. The star polymer, PSt3, with three arms and a central core was obtained by ATRP of styrene using a designed initiator with three active Br terminals and ester groups, followed by the Br terminal–Br terminal radical coupling of PSt3, which was implemented via intramolecular ATRC under high dilution conditions. A tadpole-shaped cyclic polymer (tadpole-PSt) was successfully prepared, proving that there no intermolecular side reactions that occur during the intramolecular ATRC of PSt3. Interestingly, the tadpole-PSt not only possesses a cyclic topology, but also contains a living chain, in contrast to other cyclic analogues that have been previously reported. Finally, the tadpole-PSt was used as a building block to construct a type of barbell polymer (barbell-PSt) by removing most of the solvent via vacuum distillation at the end of the intramolecular ATRC of PSt3. Size exclusion chromatography, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, 1H nuclear magnetic resonance spectroscopy and hydrolysis experiments proved that high-purity cyclic polymers (tadpole-PSt and barbell-PSt) were successfully prepared. The thermal properties of the cyclic and star polymers were analyzed using differential scanning calorimetry and thermogravimetric analysis. The results demonstrated that the formation of a cyclic topology makes a huge contribution to the increase in the glass transition temperature (Tg) and thermal stability of the polymer.

Graphical abstract: A facile approach for preparing tadpole and barbell-shaped cyclic polymers through combining ATRP and atom transfer radical coupling (ATRC) reactions

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Article information


Submitted
05 Aug 2020
Accepted
04 Sep 2020
First published
04 Sep 2020

Polym. Chem., 2020,11, 6529-6538
Article type
Paper

A facile approach for preparing tadpole and barbell-shaped cyclic polymers through combining ATRP and atom transfer radical coupling (ATRC) reactions

X. Xue, Y. Chen, K. Liang, W. Huang, H. Yang, L. Jiang, Q. Jiang, B. Jiang and H. Pu, Polym. Chem., 2020, 11, 6529
DOI: 10.1039/D0PY01116A

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