Phantom polyguanidines by ring-closing condensation polymerization: Mechanistic studies and properties investigations
Theoretical Chemistry: Electronic Structure, Dynamics, Simulation
Final Report Abstract
The project aimed at studying a new type of phantom ring-closing polymerization for the synthesis of ring polyguanidines, which is a novel sub-class of polyguanidines, and to investigate their structure by a combination of various analytical techniques supported by quantum chemical calculations. Linear polyguanidines synthesized by the reaction of diamines with guanidine hydrochloride are known. In contrast, ring polyguanidines were not known in the literature but could be of interest as ligands, catalysts, bioreceptors, antimicrobials etc. The different reactivity of primary and secondary amino groups in multifunctional amines in nucleophilic addition reactions in combination with the appropriate counter anion during condensation with guanidine salts are expected to provide phantom polymers with ring structures in the repeat unit. Based on our studies, the ring vs. linear repeat unit structure was found to depend on the type of amine used for condensation polymerization with guanidine salts. First, the amine should be at least a triamine with two p-amino and one-sec-amine group such as diethylenetriamine for the formation of ring-polyguanidines. Further, our studies showed that the spacer length between the two nitrogen atoms also play a crucial role in the final structure of the polymer. Counter ion of guanidine salt did not influence the final polymer structure.
Publications
- Phantom ring-closing condensation polymerization: Towards antibacterial oligoguanidines, Macromol. Rapid Commun. 2011, 32, 994
C. Mattheis, M. C. Schwarzer, G. Frenking, S. Agarwal
- Effect of guanidinylation on the properties of poly(2-aminoethylmethacrylate)-based antibacterial materials, Macromol. Biosci. 2013, 13, 242
C. Mattheis, H. Wang, C. Meister, S. Agarwal
(See online at https://doi.org/10.1002/mabi.201200217) - Exploring suitable oligoamines for phantom ring-closing condensation polymerization with guanidine hydrochloride, Polym. Chem. 2013, 4, 707
C. Mattheis, H. wang, M. C. Schwarzer, G. Frenking, S. Agarwal
(See online at https://doi.org/10.1039/c2py20672b) - Structural exploration of phantom oligoguanidine from asymmetric diamine and guanidine hydrochloride
H. Wang, C. Benke, M. Hermann, G. Frenking, S. Agarwal
(See online at https://doi.org/10.1002/macp.201600154)
