Size-selective shell cross-linked interior functionalized siloxane nanocages

Journal of the American Chemical Society
Young-Woong SuhHarold H Kung

Abstract

A new structure, consisting of a shell cross-linked, 2 nm size siloxane nanocage containing propylamine groups tethered to the interior face of the shell was synthesized, starting with micelles of the surfactant molecule, (triethoxysilyl)propylcetylcarbamate. After hydrolysis of the ethoxysilyl groups and condensation and capping of the silanols to form a cross-linked, one-atom-layer-thick siloxane shell, the carbamate was converted to amine, releasing the cetyl group from the structure and resulting in the desired spherical nanocage. The intermediates in the synthesis process and the final structure were characterized by 1H and 29Si NMR, DLS, TEM, and mass spectroscopy. The amine groups tethered to the interior surface of the shell react readily with ninhydrin but do not interact with the larger ZnTPP, indicating molecular size selectivity by the cross-linked shell. The structure also exhibits confinement effect in the amine-catalyzed decarboxylation of acetoacetic acid, exhibiting higher activity and higher selectivity for acetal than (aminopropyl)triethoxysilane.

References

Oct 1, 1981·Analytical Biochemistry·V K SarinR B Merrifield
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Feb 18, 2004·Angewandte Chemie·Dennis H LeungKenneth N Raymond

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Citations

Oct 28, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·QianMing WangHitoshi Tamiaki
Mar 19, 2013·Chemical Communications : Chem Comm·Zhongliang ShenMayfair C Kung
Jan 25, 2014·Chemical Communications : Chem Comm·Mayfair C KungHarold H Kung
Nov 14, 2008·Journal of the American Chemical Society·Juan D HenaoHarold H Kung
Mar 29, 2014·Journal of the American Chemical Society·Jingmei ShenHarold H Kung

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