The unique ability of the intertidal marine mussel to adhere to wet, heterogeneous surfaces has recently attracted a tremendous amount of attention.  While the natural adhesive employed by this organism is a complex mixture of proteins, the rare amino acid 3,4-dihydroxyphenylalanine (DOPA) has been identified as a common constituent that plays a pivotal role in the interfacial interactions of the adhesive plaques.  DOPA's ability to undergo hydrogen bonding, p�p aromatic interactions, and metal�ligand complexation with a variety of surface functionalities facilitates interfacial adhesion.  However, under slightly basic conditions DOPA is susceptible to oxidation which diminishes the molecules adhesive ability and leads to self-polymerization.  In this presentation, we report the synthesis of multifunctional halodopamine derivatives showing a decreased oxidation potential and an increased affinity for coordination to a variety of surfaces.  The halodopamine monomers show improved miscibility with multifunctional thiols and enes commonly used in thiol-ene polymerizations enabling solvent-free resin systems.  This presentation will describe our efforts to evaluate the effect an electron withdrawing substituent in the 2-position of DOPA analogues has on oxidation and coordination behavior, as well as evaluate the effect of the pendant catechol moiety, in the nonoxidized form, on photopolymerization kinetics, thermal, thermomechanical, and adhesive properties of the catechol modified thiol�ene networks.

Tailoring adhesion and network properties of thiol-ene networks via incorporation of halodopamine derivatives

247th National Meeting (2014)

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