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Mesoporous ethane-silicas functionalized with trans-(1R,2R)-diaminocyclohexane as heterogeneous chiral catalysts
Jiang, DM; Yang, QH; Yang, J; Zhang, L; Zhu, GR; Su, WG; Li, C
刊名CHEMISTRY OF MATERIALS
2005-11-29
DOI10.1021/cm0514084
17期:24页:6154-6160
收录类别SCI
文章类型Article
WOS标题词Science & Technology ; Physical Sciences ; Technology
类目[WOS]Chemistry, Physical ; Materials Science, Multidisciplinary
研究领域[WOS]Chemistry ; Materials Science
关键词[WOS]MOLECULAR-SIEVES ; SURFACTANT ; DESIGN
英文摘要Mesoporous ethane-silicas functionalized with trans-(1R,2R)-diaminocyclohexane were synthesized by one-step co-condensation of 1,2-bis(trimethoxysilyl)ethane and N-[(triethoxysilyl)propyl]-(-)-(1R,2R)-diaminocyclohexane using octadecyltrimethylammonium chloride as the template under basic conditions. For comparison, the mesoporous silica containing trans-(1R,2R)-diaminocyclohexane was also synthesized. The structural characterizations (X-ray powder diffraction, transmission electron microscopy, and N-2 sorption isotherms) show that the two materials have ordered two-dimensional-hexagonal mesostructure and wormhole-like structure, respectively. The integrity of the organic groups in the mesoporous materials is confirmed by Fourier transform infrared and solid-state C-13 and Si-29 cross-polarization magic-angle-spinning NMR spectroscopies. Mesoporous materials are used as catalysts for the asymmetric transfer hydrogenation of acetophenone after complexing [Rh(cod)Cl](2) to the chiral ligands, trans-(1R,2R)-diaminocyclohexane, in the mesopores. The catalyst with the ethane-bridged framework exhibits 82-96% conversion with 19-23% enantiomeric excess (ee), while the catalyst with pure-silica framework shows 48% conversion with 14% ee under identical reaction conditions. The enhanced catalytic activity of the mesoporous organosilicas is mainly caused by the specific adsorption and physical properties of the mesoporous network bridged with ethane groups, particularly the hydrophobic properties. The enantioselectivity, albeit not yet high enough, demonstrates the possibility for synthesizing a new kind of chiral solid catalysts for potential applications in asymmetric reactions.
语种英语
WOS记录号WOS:000233507600038
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被引频次:67[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/139846
专题中国科学院大连化学物理研究所
作者单位Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
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GB/T 7714
Jiang, DM,Yang, QH,Yang, J,et al. Mesoporous ethane-silicas functionalized with trans-(1R,2R)-diaminocyclohexane as heterogeneous chiral catalysts[J]. CHEMISTRY OF MATERIALS,2005,17(24):6154-6160.
APA Jiang, DM.,Yang, QH.,Yang, J.,Zhang, L.,Zhu, GR.,...&Li, C.(2005).Mesoporous ethane-silicas functionalized with trans-(1R,2R)-diaminocyclohexane as heterogeneous chiral catalysts.CHEMISTRY OF MATERIALS,17(24),6154-6160.
MLA Jiang, DM,et al."Mesoporous ethane-silicas functionalized with trans-(1R,2R)-diaminocyclohexane as heterogeneous chiral catalysts".CHEMISTRY OF MATERIALS 17.24(2005):6154-6160.
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