Azo-Derived Symmetrical Trithiocarbonate for Unprecedented RAFT Control

Bis­(2-cyanopropan-2-yl)­trithiocarbonate (TTC-bCP) is a new symmetrical trithiocarbonate with the best leaving group ever reported for reversible addition–fragmentation chain transfer (RAFT) polymerization. We propose an elegant route to obtain TTC-bCP starting from 2,2′-azobis­(2-methylpropionitri...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2021-12, Vol.143 (49), p.20585-20590
Main Authors: Ivanchenko, Oleksandr, Odnoroh, Maksym, Mallet-Ladeira, Sonia, Guerre, Marc, Mazières, Stéphane, Destarac, Mathias
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
Polymers
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Bis­(2-cyanopropan-2-yl)­trithiocarbonate (TTC-bCP) is a new symmetrical trithiocarbonate with the best leaving group ever reported for reversible addition–fragmentation chain transfer (RAFT) polymerization. We propose an elegant route to obtain TTC-bCP starting from 2,2′-azobis­(2-methylpropionitrile) (AIBN) as a donor of the 2-cyanopropan-2-yl group. TTC-bCP allowed the preparation of a high-molar-mass (M n ≈ 135 kg mol–1) methyl methacrylate–n-butyl acrylate–methyl methacrylate triblock copolymer with unprecedented control (D̵ = 1.04) in reversible-deactivation radical polymerization. Rheology measurements of this triblock copolymer showed a typical thermoplastic elastomer behavior with a steady rubbery plateau up to 120 °C.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c10031