The development of versatile carrier materials for active guest species without the need for guest modification plays a crucial role in a broad field of applications like catalysis, drug delivery, chiral separation, or wastewater purification. The challenge is to obtain unique adsorption materials with adjustable properties. The key points for the performance of such a carrier material are the matching strength of host-guest interaction to achieve a high uptake and, especially in drug delivery, the ability of a controlled desorption. Perfect candidates are cyclodextrins, being hosts for hydrophobic molecules of different sizes. In this work, we smart design a functional adsorption material based on mesoporous organosilica particles with a high surface cyclodextrin density as a versatile supramolecular host molecule for a wide range of drugs with improved storage capacity and temperature-triggered release. We present the means of porosity control of organosilica particles bearing an intrinsic high density of functional groups, like alkenes, on the inner and outer surface. These are used in thiol-ene click chemistry to achieve a high degree of functionalization with β- and γ- cyclodextrin. The adsorption of the anti-quorum-sensing agent thymol and the temperature-induced increased release are presented. As a proof of concept, we demonstrate the antibacterial activity of thermally induced released thymol against S. aureus , resulting in a reduction of metabolic activity of bacteria. This improvement of an adsorption material based on porosity-controlled organosilica particles by attaching cyclodextrin hosts broadens its applicability and enables its direct use in catalysis, adsorption, chiral separation, or enhanced drug delivery. • Porosity control over micelle assisted organosilica nanoparticle synthesis • Highly functionalized organosilica with supramolecular cyclodextrins • Photoinitiated thiol-ene click chemistry on styrene bridged silica • Temperature controlled release of thymol via host-guest interaction • Proof of concept antibacterial activity of triggered organosilica colloids
Baumgarten et al. (Sun,) studied this question.