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Synthesis of an amphiphilic spiro ‐multiblock copolymer via thiol‐ene click chemistry
Author(s) -
Kim KyungSu,
Mohanty Aruna Kumar,
Ahn Junyoung,
Bang Meehee,
Lee Hong Chan,
Joo SangWoo,
Jeon Heung Bae,
Chang Taihyun,
Paik Hyunjong
Publication year - 2020
Publication title -
journal of polymer science
Language(s) - English
Resource type - Journals
eISSN - 2642-4169
pISSN - 2642-4150
DOI - 10.1002/pola.29470
Subject(s) - norbornene , polymer chemistry , copolymer , click chemistry , chemistry , polymerization , polystyrene , ethylene glycol , ene reaction , azide , chain transfer , radical polymerization , organic chemistry , polymer
A multiblock [poly(ethylene oxide)‐b‐ spiro ‐polystyrene] ([(PEO‐b‐ spiro ‐PS)]) copolymer with a topologically novel architecture was synthesized using thiol‐ene step‐growth polymerization reaction. Spiro ‐PS with dimercapto groups as the hard segment was synthesized in three main steps: (a) preparation of tetra‐arm PS by atom transfer radical polymerization and the conversion of the chain‐end group to azide functionality, (b) alkyne‐azide click coupling reaction to synthesize a tricyclic PS, and (c) tactical ring opening of the tricyclic PS through disulfide/thiol redox reaction. The PEO soft segment was obtained as chain‐ends modified with norbornene groups. Finally, the hydrothiolation of the highly reactive norbornene chain‐ends of polyethylene glycol with the dimercapto groups of spiro ‐PS produced the multiblock ([(PEO‐b‐ spiro ‐PS)]) copolymer in quantitative yield. The multiblock copolymer was characterized using size‐exclusion chromatography, proton nuclear magnetic resonance spectroscopy, Fourier‐transform infrared spectroscopy, X‐ray photoelectron spectroscopy, and Raman spectroscopy. © 2019 Wiley Periodicals, Inc. J. Polym. Sci. 2020 , 58 , 132–138