ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
2019_PAH_00_Revision_Full.pdf (1.24 MB)
0/0

Poly(Boc-acryloyl hydrazide): The importance of temperature and RAFT agent degradation on its preparation

preprint
revised on 14.08.2019 and posted on 14.08.2019 by Oliver Creese, Pavan Adoni, Guanlong Su, Andrey V. Romanyuk, Paco Fernandez-Trillo

Poly(acryloyl hydrazide) is a versatile polymer scaffold readily functionalised through post-polymerisation modification with aldehydes to yield polymers for biological applications. However, its polymerisation is affected by nucleophilic degradation of the RAFT agent that leads to early termination, an issue often overlooked in the polymerisation of primary acrylamides. Here we report the effect of temperature on the RAFT polymerisation of N’-(tert-butoxycarbonyl)acryloyl hydrazide (1) and demonstrate that by carefully selecting this polymerisation temperature, a balance between rate of polymerisation and rate of degradation of the RAFT agent can be achieved. This way a greater control over the polymerisation process is achieved, allowing the synthesis of Boc-protected poly(acryloyl hydrazide) with higher degrees of polymerisation than those achieved previously, while still maintaining low dispersities. We believe our results should be of importance to those working on the RAFT polymerization of primary and secondary (meth)acrylamides and monomers with nucleophilic moieties.

Funding

BBSRC Midlands Integrative Biosciences Training Partnership MIBTP (BB/M01116X/1)

European Union’s Horizon 2020 Research and Innovation Programme (Marie Sklodowska-Curie Grant Agreement No 795082)

History

Email Address of Submitting Author

f.fernandez-trillo@bham.ac.uk

Institution

University of Birmingham

Country

United Kingdom

ORCID For Submitting Author

0000-0002-6680-5683

Declaration of Conflict of Interest

No conflict of interest

Exports