Stimuli-Responsive Functionalization Strategies to Spatially and Temporally Control Surface Properties: Michael vs Diels–Alder Type Additions

Abstract

Stimuli-responsive self-assembled monolayers (SAMs) are used to confer switchable physical, chemical, or biological properties to surfaces through the application of external stimuli. To obtain spatially and temporally tunable surfaces, we present microcontact printed SAMs of a hydroquinone molecule that are used as a dynamic interface to immobilize different functional molecules either via Diels-Alder or Michael thiol addition reactions upon the application of a low potential. In spite of the use of such reactions and the potential applicability of the resulting surfaces in different fields ranging from sensing to biomedicine through data storage or cleanup, a direct comparison of the two functionalization strategies on a surface has not yet been performed. Although the Michael thiol addition requires molecules that are commercial or easy to synthesize in comparison with the cyclopentadiene derivatives needed for the Diels-Alder reaction, the latter reaction produces more homogeneous coverages under similar experimental conditions.

High-Throughput Cell Motility Studies on Surface-Bound Protein Nanoparticles with Diverse Structural and Compositional Characteristics

“…External factors, provided by the extracellular matrix (ECM), operate at every stage of the movement cycle, stabilizing protrusions and maintaining the direction of migration . Thus, cell shape and mobility are governed by the dimensionality of surface decoration (i.e., three-dimensional, two-dimensional (2D), or one-dimensional in the case of a single fiber of collagen), − density and orientation of the ECM ligands (i.e., nanoscale or microscale structures of the ECM), − and stiffness (i.e., mechanical properties of the substrate) . Although many efforts have been made to reproduce in vitro the complex aspects of physiological conditions, further advancements in nanofabrication and synthetic self-assembly are still needed .…”

Visualized Degradation of Poly(alkynoate)s Toward Diols and Structure Controlled Multifunctional N-Heterocyclic Compounds

“…μCP as a kind of soft lithography possesses many advantages including high resolution, very short reaction times, simple large-area patterning, and low cost, etc. 34,35 Certainly, it can solve the disadvantages encountered in microfabrication, which is the basic technology used for making all microelectronic systems, such as high cost, complex facilities and technologies for high-energy radiation needed and limitation to extremely flat silicon substrates. μCP allows the patterned transfer of a molecular ink onto a surface using an elastomeric stamp.…”

Visualized Degradation of CO 2 -Based Unsaturated Polyesters toward Structure-Controlled and High-Value-Added Fluorophores

“…μCP as a kind of soft lithography possessing many advantages, including high resolution, very short reaction times, simple large-area patterning, low cost, and so forth. [40][41][42] Certainly, it can help to solve the disadvantages encountered in microfabrication, which is the basic technology used in making all microelectronic systems, such as high cost, complex facilities and technologies for high-energy radiation needed, and limitations to extremely flat silicon substrates. μCP allows the patterned transfer of a molecular ink onto a surface using an elastomeric stamp.…”