Tailoring the Hydrophilic/Lipophilic Balance of Clickable Mesoporous Organosilicas by the Copper-Catalyzed Azide−Alkyne Cycloaddition Click-Functionalization

Achraf Noureddine (1) , Philippe Trens (1) , Xavier Cattoën (2, 1) , Michel Wong Chi Man (1) , Guillaume Toquer (3)

1 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 NEEL - OPTIMA - Optique et Matériaux
3 ICSM - UMR 5257 - Institut de Chimie Séparative de Marcoule

We have designed and synthesized a clickable bridged silsesquioxane material featuring pendant alkyne chains as an aggregate of golf-ball-like nanoparticles, as evidenced by scanning electron microscopy (SEM), transmission electron microscopy (TEM), and small- and wide-angle X-ray scattering (SWAXS). Using the copper-catalyzed azide−alkyne cycloaddition reaction with a range of organic azides of variable characteristics, we transformed this parent bridged silsesquioxane into new materials with tunable hydrophilic/lipophilic balance in high conversions while preserving the original morphology. N2, cyclohexane, and water sorption experiments were used to quantify the affinity of these materials toward the sorbates through the determination of their Henry’s constants. This resulted in the following hydrophilic scale: M-OH > M-PEG > M-C6 > M-Ph > M-F > M-C16, which was mostly confirmed by SWAXS measurements.

Domaines: Matériaux

Achraf Noureddine, Philippe Trens, Xavier Cattoën, Michel Wong Chi Man, Guillaume Toquer. Tailoring the Hydrophilic/Lipophilic Balance of Clickable Mesoporous Organosilicas by the Copper-Catalyzed Azide−Alkyne Cycloaddition Click-Functionalization. Langmuir, 2014, 30 (41), pp.12297-12305. ⟨10.1021/la503151w⟩. ⟨hal-01082256⟩