Functionalized nanoparticles using active ester monomers as shell component

POLY 199

Nadine Metz, metz@uni-mainz.de1, Birger Lange, langeb@uni-mainz.de2, Patrick Theato, theato@uni-mainz.de3, and Rudolf Zentel, zentel@mail.uni-mainz.de2. (1) Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, Mainz, 55099, Germany, (2) Institut fuer organische Chemie, Johannes Gutenberg-Universitaet Mainz, Duesbergweg 10-14, Mainz, 55099, Germany, (3) Institute of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, Mainz, 55099, Germany
The application of active esters in peptide chemistry is known for a long time. Meanwhile, the advantageous use of active esters also found it's way into polymer science. Reactive polymers have found broad scientific applications as synthetic platforms for the versatile preparation of functional polymers. However, mainly active ester polymers based on N-hydroxysuccinimide (NHS) are used in polymer science in the form of NHS-(meth)acrylates. Controlled radical polymerization techniques gained a lot of interest due to the control of chain length, polydispersity, and microstructure of the respective polymers. The most important processes are nitroxide-mediated polymerization (NMP), atom transfer radical polymerization (ATRP) and reversible addition fragmentation chain transfer (RAFT) polymerization. In the recent years these polymerization techniques have been used to polymerize active ester monomers. The investigation of polymer nanoparticles is a rapidly developing area in science. Nanoparticles prepared by emulsion polymerization, a well-established procedure for coatings, paints, and in flocculation processes, are increasingly used in applications in the area of photonics, diagnostics and catalysis. Within the present study we tried to combine polymeric active ester chemistry with the emulsion polymerization technique to prepare functionalized polymer nanoparticles. We succeeded in the synthesis of functional core-shell colloids with the pentafluorphenyl acrylate as a reactive shell material. The active ester shell can be reacted with a variety of different amines, yielding the respective amide. For example it is possible to stabilize them with hexamethylenediamine or they can also be used for surface modification with biomaterials and subsequent growth of gold particles on the surface. Depending on the concentration of the amine and the reaction time one can regulate the conversion to the amide. This allows multistep processes, where different amines with different functionalities can be attached to the colloids.
 

General Papers: Polymers in Nanotechnology
6:00 PM-8:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Polymer Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007