Switchable self-assembly of a bioinspired alkyl catechol at a solid/liquid interface: Competitive interfacial, noncovalent, and solvent interactions

The large tendency of catechol rings to adsorb on surfaces has been studied by STM experiments with molecular resolution combined with molecular-dynamics simulations. The strong adhesion is due to interactions with the surface and solvent effects. Moreover, the thermodynamic control over the differential adsorption of 1 and the nonanoic solvent molecules has been used to induce a new temperature-induced switchable interconversion. Two different phases that differ in their crystal packing and the presence of solvent molecules coexist upon an increase or decrease in the temperature. These results open new insight into the behavior of catechol molecules on surfaces and 2D molecular suprastructures. Recognized strong adhesion and organization of catechols on surfaces has been used as a means to study the main parameters that control molecular self-assembly processes on surfaces, namely, the energetics (molecule/molecule, molecule/surface interactions) and thermodynamics (solvent effects; see figure). This knowledge is used to establish temperature-induced switchable 2D supramolecular structures Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.