Volume 3 Supplement 1

6th German Conference on Chemoinformatics, GCC 2010

Open Access

Dissecting the role of guanidine copper complexes in atom transfer radical polymerization by density functional theory

Journal of Cheminformatics20113(Suppl 1):P28

DOI: 10.1186/1758-2946-3-S1-P28

Published: 19 April 2011

Since the development of the living / controlled radical polymerization method ATRP (= atom transfer radical polymerization) in 1995 [1] new catalysts for this reaction have been intensively investigated. This method conquered rapidly numerous fields in chemistry ranging from organic and polymer synthesis to materials science and nanotechnology.

Guanidine copper complexes display high activity in ATRP of styrene but the factors imposed on the activator/deactivator equilibrium are multifaceted [2]. Herein we report on new copper complexes with the guanidine ligand 1,3,3-tetramethyl-2-(quinolin-8-yl)guanidine which produce polystyrene with a narrow weight distribution and in high yields. Kinetic studies showed that the polymerization is of living character. Structural characterization leads us to a proposal for the activator and deactivator structures which control the ATRP (Figure 1). By density functional theory, we were able to dissect the influences on the position of the equilibrium between the Cu(I) and Cu(II) complex (ligand donor strength, halogene bond strength, redox potential, coordinative space) operating the polymerization process.
Figure 1

Activator/deactivator equilibrium in ATRP.

Authors’ Affiliations

Fakultät Chemie, Technische University of Dortmund
Department of Chemistry, University of Paderborn


  1. Wang J-S, Matyjaszewski K: Controlled Radical Polymerization. Atom Transfer Radical Polymerization in the Presence of Transition Metal Complexes. J Am Chem Soc. 1995, 117: 5614-5615. 10.1021/ja00125a035.View ArticleGoogle Scholar
  2. Bienemann O, Haase R, Flörke U, Döring A, Kuckling D, Herres-Pawlis S: Neue Bisguanidin-Kupfer-Komplexe und ihre Anwendung in der ATRP. Z Naturforsch. 2010, 65b: 798-806.Google Scholar


© Herres-Pawlis et al; licensee BioMed Central Ltd. 2011

This article is published under license to BioMed Central Ltd. This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.