Phantom ring-closing condensation polymerization: Towards antibacterial oligoguanidines

Claudia Mattheis, Martin C. Schwarzer, Gernot Frenking, Seema Agarwal

科研成果: 期刊稿件文章同行评审

8 引用 (Scopus)

摘要

The first example of phantom ring-closing condensation polymerization for the synthesis of oligoguanidines is presented. A new oligoguanidine with a ring structure was achieved in one step by the condensation reaction of a triamine, like diethylenetriamine, with guanidine hydrochloride. The condensation reaction proceeded by selective ring-closure towards the formation of five-membered rings in the oligomer backbone. The resulting polymer repeat unit structure was different from the starting monomers (phantom polymer) and was formed by elimination of three molecules of ammonia per repeat unit. The inter-, intra-, and inter-molecular reaction sequences led to the new structure as proved by different spectroscopic techniques (atmospheric pressure chemical-ionization mass spectrometry, and one-dimensional and two-dimensional homo- and heteronuclear correlation NMR experiments) as well as supported by quantum chemical investigations. Preliminary results regarding antibacterial use of the resulting oligoguanidine were also promising and showed its effect within 15-30 min as an antibacterial material. Phantom ring-closing condensation polymerization has given new oligoguanidines with a ring structure as proved by spectroscopy and quantum chemical calculations. They are promising candidates as fast antibacterial materials.

源语言英语
页(从-至)994-999
页数6
期刊Macromolecular Rapid Communications
32
13
DOI
出版状态已出版 - 1 7月 2011
已对外发布

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