Jump to main content
Jump to site search

Issue 13, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 13 Feb 2017, accepted on 14 Mar 2017 and first published on 15 Mar 2017


Article type: Paper
DOI: 10.1039/C7PY00236J
Citation: Polym. Chem., 2017,8, 2093-2104
  • Open access: Creative Commons BY license
  •   Request permissions

    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. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements