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A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition
Author(s) -
Göbel Ronald,
Stoltenberg Marcus,
Krehl Stefan,
Biolley Christine,
Rothe Regina,
Schmidt Bernd,
Hesemann Peter,
Taubert Andreas
Publication year - 2016
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201500638
Subject(s) - chemistry , cycloaddition , surface modification , epoxide , isocyanate , mesoporous silica , monolith , polymer chemistry , metathesis , olefin fiber , mesoporous material , organic chemistry , catalysis , polyurethane , polymerization , polymer
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.