Issue 13, 2017

Polymers from sugars and CO2: ring-opening polymerisation and copolymerisation of cyclic carbonates derived from 2-deoxy-d-ribose

Abstract

Bio-based aliphatic polycarbonates (APCs) are attractive synthetic materials for biomedical applications because of their biodegradabilty and biocompatability properties. A high yielding 3-step process that utilises CO2 as a C1 synthon is presented for converting raw sugar, 2-deoxy-D-ribose into a novel 6-membered cyclic carbonate for ring-opening polymerisation (ROP) into carbohydrate-based APCs. The α- and β-anomers of the monomer could be isolated and revealed very different polymerisability, as rationalised by DFT calculations. Whereas the β-anomer could not be polymerised under the conditions tested, organocatalytic homopolymerisation of the α-anomer, in solution at room temperature (rt) or under melt conditions, yielded highly insoluble polycarbonates, composed of both cyclic and linear topologies, and exhibiting a glass transition temperature (Tg) of ∼58 °C. Random copolymers with controllable incorporation of this new sugar monomer were prepared with trimethylene carbonate (TMC) at rt in the bulk or in solution with Mn up to 64 000 g mol−1. With increasing sugar content, the Tg values of the copolymers increased and their thermal degradability was enhanced, giving access to a new class of APCs with tailored properties.

Graphical abstract: Polymers from sugars and CO2: ring-opening polymerisation and copolymerisation of cyclic carbonates derived from 2-deoxy-d-ribose

Supplementary files

Article information

Article type
Paper
Submitted
13 Feb 2017
Accepted
14 Mar 2017
First published
15 Mar 2017
This article is Open Access
Creative Commons BY license

Polym. Chem., 2017,8, 2093-2104

Polymers from sugars and CO2: ring-opening polymerisation and copolymerisation of cyclic carbonates derived from 2-deoxy-D-ribose

G. L. Gregory, G. Kociok-Köhn and A. Buchard, Polym. Chem., 2017, 8, 2093 DOI: 10.1039/C7PY00236J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements