Chlorophyll derivatives as catalysts and comonomers for atom transfer radical polymerizations

Bernadetta Gajewska, Samuel Raccio, Kyle J. Rodriguez, Nico Bruns

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Copper trisodium chlorophyllin is obtained from natural chlorophyll, and is widely used as a major green food colorant in cosmetics and in medical devices. Copper chlorophyllin also proves to be an efficient catalyst and comonomer for atom transfer radical polymerizations (ATRP). Aqueous ATRP of poly(ethylene glycol) acrylate (PEGA) results in PEGA-chlorophyllin copolymers with narrow molecular weight distributions and a controlled content of chlorophyllin. The reactions proceed with first order kinetics, and the polymer's molecular weight increases with conversion. The resulting copolymers could find application in drug delivery and in biomedical materials, or as solar energy harvesting materials. In order to suppress the incorporation of the catalyst into the growing polymer chains, the vinyl bond of chlorin e6, one of the major porphyrin components of chlorophyllin, is deactivated by hydrobromination and hydration. Complexation of copper by the porphyrin leads to a bio-derived catalyst which mediates the polymerization of PEGA, yielding homopolymers with molecular weights ranging from 4000-5000 g mol-1 and dispersities ≤ 1.11. UV-Vis spectroscopy indicates that chlorophyllin is stable during the polymerization. Copper chlorophyllin is a plant-derived compound from a renewable feedstock that can be used for a more environmentally friendly route to ATRP.

LanguageEnglish
Pages125-135
Number of pages11
JournalPolymer Chemistry
Volume10
Issue number1
Early online date13 Nov 2018
DOIs
Publication statusPublished - 7 Jan 2019

Fingerprint

Atom transfer radical polymerization
Chlorophyll
Polymerization
Polyethylene glycols
Derivatives
Copper
Catalysts
Porphyrins
Ethylene Glycol
Copolymers
Molecular weight
Molecular Weight
Cosmetics
Energy harvesting
Polymers
Molecular weight distribution
Homopolymerization
Ultraviolet spectroscopy
Complexation
Drug delivery

Keywords

  • chlorophyll
  • copper chlorophyllin
  • PEGA-chlorophyllin copolymers
  • atom transfer radical polymerizations (ATRP)

Cite this

Gajewska, Bernadetta ; Raccio, Samuel ; Rodriguez, Kyle J. ; Bruns, Nico. / Chlorophyll derivatives as catalysts and comonomers for atom transfer radical polymerizations. In: Polymer Chemistry. 2019 ; Vol. 10, No. 1. pp. 125-135.
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Chlorophyll derivatives as catalysts and comonomers for atom transfer radical polymerizations. / Gajewska, Bernadetta; Raccio, Samuel; Rodriguez, Kyle J.; Bruns, Nico.

In: Polymer Chemistry, Vol. 10, No. 1, 07.01.2019, p. 125-135.

Research output: Contribution to journalArticle

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