Adhesion is one of the most ubiquitous practical applications at surfaces. With today’s society calling increasingly for more reusable and “green” alternatives, the demand for readily reversible adhesives has triggered many studies into this field, in particular by incorporating molecular photoswitches into composite materials. Responsive polymers can act as reversible adhesives, but their employment brings about synthetic drawbacks and challenges in reproducibility and reusability. Here, our results demonstrate that even a low molecular weight photoswitch can serve as an on-demand adhesive when the intermolecular interactions are sufficiently strong. We show that readily accessible arylazoisoxazoles display a fast photoreversible solid-to-liquid phase transition and perform as excellent photoreversible adhesives, with a remarkable durability over 10 immediate reuse cycles without a loss in adhesive strength or an increase in the unprecedented response time. Furthermore, the versatility of photoreversible adhesion is shown at various surfaces ranging from polymeric materials to metals, demonstrating a wide field of potential application.

Carboxymethyl cellulose functionalized with nucleic acids, β-cyclodextrin and arylazopyrazole photoisomerizable units self-assembles into stimuli-responsive hydrogels.

Bidirectional photoswitching of arylazopyrazoles with visible light is enabled by substitution with pyrrolidine and piperidine in the ortho-position of the phenyl ring. The absorption maxima were red-shifted and the molar absorption coefficients in the visible range increased significantly, allowing the use of blue light (λ = 465 nm) for the E → Z isomerization and red light (λ = 600 nm) for the Z → E isomerization. N-Methylation of the pyrazole leads to an excellent thermal stability of the Z isomer.

Molecular photoswitches play a vital role in the development of responsive materials. These molecular building blocks are particularly attractive when multiple stimuli can be combined to bring about physical changes,...