Journal
ACS MACRO LETTERS
Volume 6, Issue 3, Pages 287-291Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsmacrolett.7b00100
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Funding
- National Health and Medical Research Council [APP1099321]
- Australian Research Council [FT110100284, DP140100951]
- ARC Centre of Excellence in Convergent Bio-Nano Science and Technology [CE140100036]
- University of Queensland [UQECR1607665]
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The hydrolytic degradation of widely used cyano-containing, acid bearing trithiocarbonate reversible addition fragmentation chain-transfer (RAFT) agents has been identified and shown to effect the RAFT polymerization and end-group fidelity of PMMA polymers. The hydrolysis occurred when the RAFT agents were stored under the recommended conditions. Degradation was identified in both commercially available and popular synthetic RAFT agents. H-1 and C-13 NMR as well as mass spectroscopy show that the cyano functionality hydrolyzes to the amide adduct. Doping of this amide degradation product into RAFT polymerizations of MMA results in increased dispersities and changes in expected end-group ability to identify this degradation product and remove it from the RAFT agent before use will allow better control over polymer properties and postmodification processes commonly used in complex polymer systems, nanomedicines, and bioconjugates.
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