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The design of novel heterogeneous catalysts with multiple adjacent functionalities is of high interest to heterogeneous catalysis. Herein, we report a method to obtain a majority of bifunctional acid-base pairs on SBA15. Aniline reacts with SBA15 by opening siloxane bridges leading to N -phenylsilanamine-silanol pairs. In contrast with ammonia treated surfaces, the material is stable under air/moisture. Advanced solid state MAS NMR (2D 1 H- 1 H double-quantum, 1 H- 13 C HETCOR) experiments and dynamic nuclear polarization enhanced 29 Si and 15 N spectra demonstrate both the close proximity between the two moieties and the formation of a covalent Si-N surface bond and confirm the design of vicinal acid-base pairs. This approach was successfully applied to the design of a series of aniline derivatives of bifunctional SBA15. A correlation between the substituent effects on the aromatic ring (Hammett parameters) with the kinetics of a model Knoevenagel reaction is observed.

Atomic-level organization of vicinal acid–base pairs through the chemisorption of aniline and derivatives onto mesoporous SBA15