CATECHOL-BASED ADHESIVES AND COATINGS: A BIOMIMETIC SYNTHETIC APPROACH

DANIEL RUIZ MOLINA; JOSEP SEDÓ VERGARA; BUSQUÉ, FÉLIX; JAVIER SAIZ-POSEU; MIGUEL A. MORENO-VILLAÉCIJA; CAROLINA CASAGUALDA; FABIANA NADOR; JUAN MANCEBO ARACIL

Potrero de los Funes, San Luis

Simposio; XXI Simposio Nacional de Química Orgánica; 2017

Bahía Blanca

Inspired by the pioneering work of Messersmith et al., one of the most widespreadmethodologies used over the last years for control of the surface properties has been the melanin-like oxidative polymerization of dopamine into a polydopamine (PDA) primer coating, followed by its functionalization with appropriate functional groups. In PDA, catechols and quinones are assumed to play complementary roles: on the one hand, o-dihydroxyl groups in nonoxidized catechol moieties presumably confer adhesion tosubstrates; on the other hand, residual, highly electrophilic o-quinones act as reactive points for the covalent attachment of functional side chains. However, despite its versatility and simplicity, PDA modification relies on the existence of a sufficient amount of reactivegroups in the primer coating, which cannot be accurately controlled and, because of PDA insolubility, restricted to in situ polymerization methodologies. Recently, we have reported the development of an alternative, simpler approach tofabricate catechol-based material. In this novel strategy, a single monomer bearing both a catechol ring and at least one desired functional side chain (i.e., designed to carry a maximum amount of functional groups) is first synthesized and then polymerized by means of a simple and inexpensive procedure consisting of treatment with ammonia in aerobic conditions. Compared to PDA, the main differences would be, first, the nitrogen source -which is endogenous in the case of catecholamines and external in our case (ammonia)- and, more importantly, the fact that this novel approach does not rely on uncontrolledresidual reactivity in order to introduce a specific functionality in the coating because it is already built in the catecholic monomer. Following this approach we have fabricated different families of coatings and nanoparticless of applicability as biosurfaces, drug delivery carriers and/or water treatment.