A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition

Ronald Göbel (1) , Marcus Stoltenberg (1) , Stefan Krehl (1) , Christine Biolley (2) , Regina Rothe (3) , Bernd Schmidt (1) , Peter Hesemann (2) , Andreas Taubert (1)

1 Institut für Chemie [Universität Potsdam] | Institute of Chemistry [University of Potsdam]
2 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
3 Max Planck Institute of Colloids and Interfaces

We have synthesized mesoporous silica (monoliths) with defined surface chemistry by means of a number of addition reactions: (i) coupling of an isocyanate to a surface-immobilized thiol, (ii) addition of an epoxide to a surface-immobilized thiol, (iii) cross-metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne-functionalized silica monolith with an azide. Functionalization of the mesopores was observed, but there are significant differences between individual approaches. Isocyanate and epoxide additions lead to high degrees of functionalization, whereas olefin metathesis and [2+3] cycloaddition are less effective. We further show that the efficiency of the modification is about twice as high in mesoporous silica particles than in macroscopic silica monoliths.

Domaines: Matériaux

Ronald Göbel, Marcus Stoltenberg, Stefan Krehl, Christine Biolley, Regina Rothe, et al.. A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition. European Journal of Inorganic Chemistry, 2015, 2015, pp.2088-2099. ⟨10.1002/ejic.201500638⟩. ⟨hal-01390624⟩