Chiral mesoporous organosilicas with R-(+)-Binol integrated in the framework
โ Scribed by Peiyuan Wang; Jie Yang; Jian Liu; Lei Zhang; Qihua Yang
- Book ID
- 104055735
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- English
- Weight
- 557 KB
- Volume
- 117
- Category
- Article
- ISSN
- 1387-1811
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โฆ Synopsis
Bifunctionalized chiral mesoporous organosilicas with both R-(+)-Binol and ethylene moieties integrated in the framework was synthesized by co-condensation of 1,2-bis(trimethoxysilyl)ethane (BTME) and (R)-2,2 0 -dimethoxy-6,6 0 -di-[(2-trimethoxysilyl)-ethenyl]-1,1 0 -binaphthyl (R-MMB) in acidic medium using P123 as template for the first time. With the molar fraction of R-MMB increasing from10 to 20% in the initial mixture, the mesostructure of the material changes from a well-ordered 2D hexagonal mesostructure to a worm-like structure. The materials have a pore diameter in the range of 4.8-5.2 nm with BET surface areas varying from 356 to 894 m 2 g ร1 . The results of FT-IR, 13 C and 29 Si solid-state NMR shows the integration of the organic groups in the material though some Si-C bond cleavage was observed during the synthesis. The circular dichroism spectrum of the material dissolved in NaOH confirms that the chirality of R-(+)-Binol in the material remains unchanged compared with the molecular precursor. The hydroxyl groups of the R-(+)-Binol units were liberated by treatment of the material with BBr 3 . The resultant materials were used in Ti-promoted asymmetric addition of diethylzinc to benzaldehyde. High catalytic activity (99%) with moderate enantioselectivity (39.7%) was achieved, which also confirms that R-Binol was incorporated in the PMOs successfully.
๐ SIMILAR VOLUMES
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