Journal
CHEMCATCHEM
Volume 7, Issue 6, Pages 993-1003Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201402995
Keywords
basicity; hydrophobic effect; ionic liquids; mesoporous materials; polymers
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Funding
- National Natural Science Foundation of China [21136005, 21303084, 21476109]
- Jiangsu Provincial Science Foundation for Youths [BK20130921]
- Specialized Research Fund for the Doctoral Program of Higher Education [20133221120002]
- Scientific Research and Innovation Project for College Graduates of Jiangsu Province [KYLX_0766]
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Mesoporous poly(ionic liquid)s were synthesized by radical copolymerization of the ionic liquid 1-aminoethyl-3-vinylimidazolium bromide with divinylbenzene plus the ion exchange of bromide anions with hydroxyls. Characterizations revealed the high ionic liquid content, large surface area, and hydrophobicity for the sample prepared with equimolar amounts of ionic liquid and divinylbenzene, with good accessibility to organic compounds and resistance to CO2/H2O contamination. The mesoporous copolymer behaved as a superior and recyclable solid-base catalyst for solvent-free Knoevenagel condensation of benzaldehyde with ethyl cyanoacetate, giving the much higher turnover frequency of 304h(-1) (yield 99%, 0.5h) than those of the nonporous analogues, commercial strong basic resins, and even homogeneous NaOH. The high activity was confirmed by Knoevenagel condensation with various substrates and Claisen-Schmidt condensation. A possible synergistic Lewis-BrOnsted dual-base-center mechanism is proposed for understanding the catalytic behavior.
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