Catechol containing polymers have become an attractive field of research in materials science, because of their strong attachment to a variety of surfaces, which is promising for a large variety of surface applications.1 Multiple catechol functionalities at a polymer chain will lead to considerably stronger attachment than a single anchoring moiety. We present a strategy to obtain well-defined polystyrene derivatives bearing multiple catechol moieties via carbanionic polymerization. This polymerization method demands particular protecting groups to prevent proton abstraction or cleavage under harsh alkaline conditions.2 The newly developed catechol containing vinyl monomers 4-vinyl catechol acetonide (4-VCA) and 3-vinyl catechol acetonide (3-VCA) were synthesized in several steps. The monomers can be polymerized via carbanionic polymerization to obtain poly(vinyl catechol acetonide)s in a wide molecular weight range from 2,500 to 80,000 g/mol with PDIs below 1.10. The key advantage of these polymer structures is the quantitative removal of the acetonide protecting groups under mild acidic conditions. A precise method to investigate monomer reactivity in copolymerizations is the in-situ monitoring via real-time 1H NMR kinetics.3 The living anionic polymerization is monitored by measuring proton NMR spectra during chain growth, enabling an exact determination of the copolymers' microstructure (see figure). The new monomers enable us to control the microstructure of catechol containing copolymers in a concurrent copolymerization. The resulting polymers are highly promising for surface or interface modification and tailoring. [1] H. Lee, Y. Lee, A. R. Statz, J. Rho, T. G. Park, P. B. Messersmith, Adv. Mater. 2008, 20, 1619. [2] A. Hirao, S. Loykulnant, T. Ishizone, Prog. Polym. Sci. 2002, 27, 1399. [3] A. Natalello, M. Werre, A. Alkan, H. Frey, Macromolecules 2013, 46, 8467.

Novel catechol-containing vinyl monomers for carbanionic Polymerization: In Situ monitoring of the formation of poly(styrene-co-vinyl catechol) copolymers by carbanionic living copolymerization

251st National Meeting (2016)

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