One-pot multi-step reactions based on thiolactone chemistry: A powerful synthetic tool in polymer science

[Display omitted] •The aminolysis of a thiolactone is followed by a thiol-click reaction of choice.•Amine-thiol-ene reaction yields diversely substituted polyamides and polyurethanes.•Double modification of polythiolactones can be performed using two approaches.•An iterative protocol yields multi-fu...

Full description

Saved in:
Bibliographic Details
Published in:European polymer journal 2015-01, Vol.62, p.247-272
Main Authors: Espeel, Pieter, Du Prez, Filip E.
Format: Article
Language:English
Subjects:
Amine-thiol-ene conjugation
Amines
Functionalized polymers
Modular
Networks
One-pot multi-step click chemistry
Scavengers
Synthesis
Thiolactone chemistry
Thiols
Versatility
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:[Display omitted] •The aminolysis of a thiolactone is followed by a thiol-click reaction of choice.•Amine-thiol-ene reaction yields diversely substituted polyamides and polyurethanes.•Double modification of polythiolactones can be performed using two approaches.•An iterative protocol yields multi-functionalized sequence-defined oligomers. One-pot multi-step reactions based on thiolactone chemistry emerged as a powerful tool to prepare tailor-made, multi-functionalized polymer architectures in a one-pot and elegant manner. This feature article highlights the most important features of this approach, demonstrated in various reactive systems including (bio-based) linear polymers, heterotelechelic polymers, polymeric networks and heterogeneous supports. This overview clearly reveals its remarkable versatility involving modular synthesis and double modification of polymers: thiolactones can be opened by a wide variety of functional amines and the released thiol can react with thiol 'scavengers’ of choice.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2014.07.008