TY - JOUR
T1 - Lipidic Mesophases as Novel Nanoreactor Scaffolds for Organocatalysts
T2 - Heterogeneously Catalyzed Asymmetric Aldol Reactions in Confined Water
AU - Duss, Michael
AU - Salvati Manni, Livia
AU - Moser, Laurent
AU - Handschin, Stephan
AU - Mezzenga, Raffaele
AU - Jessen, Henning J.
AU - Landau, Ehud M.
N1 - Funding Information:
was partially supported by the Forschungskredit (FK-15-083) of the University of Zurich to M.D.
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/2/7
Y1 - 2018/2/7
N2 - The unique molecular architecture of lipidic cubic phases (LCPs) and their cubosome dispersions comprise a well-defined, curved bilayer that spans the entire three-dimensional (3-D) material space, encompassing a network of two periodic, curved, and nonintersecting 3-D aqueous channels. The ensuing large lipid/water interfacial area makes these biomaterials an interesting matrix for the lateral immobilization of organocatalysts to catalyze organic reactions in confined water. Herein, we report for the first time the design, synthesis, assembly, and characterization of catalytically active LCPs and cubosomes and demonstrate their applicability as self-assembled, biomimetic, and recyclable nanoreactor scaffolds. Small-angle X-ray scattering, cryo-transmission electron microscopy, and dynamic light scattering were applied for the characterization of the mesophases. These mesophases can be recycled and enable efficient catalytic activity as well as modulation of the diastereo- and enantioselectivity for the aldol reaction of several benzaldehyde derivatives and cyclohexanone in water.
AB - The unique molecular architecture of lipidic cubic phases (LCPs) and their cubosome dispersions comprise a well-defined, curved bilayer that spans the entire three-dimensional (3-D) material space, encompassing a network of two periodic, curved, and nonintersecting 3-D aqueous channels. The ensuing large lipid/water interfacial area makes these biomaterials an interesting matrix for the lateral immobilization of organocatalysts to catalyze organic reactions in confined water. Herein, we report for the first time the design, synthesis, assembly, and characterization of catalytically active LCPs and cubosomes and demonstrate their applicability as self-assembled, biomimetic, and recyclable nanoreactor scaffolds. Small-angle X-ray scattering, cryo-transmission electron microscopy, and dynamic light scattering were applied for the characterization of the mesophases. These mesophases can be recycled and enable efficient catalytic activity as well as modulation of the diastereo- and enantioselectivity for the aldol reaction of several benzaldehyde derivatives and cyclohexanone in water.
KW - aqueous chemistry
KW - asymmetric aldol reaction
KW - catalytic lipidic cubic phases and cubosomes
KW - heterogeneous catalysis
KW - self-assembly
UR - http://www.scopus.com/inward/record.url?scp=85041928859&partnerID=8YFLogxK
U2 - 10.1021/acsami.7b19740
DO - 10.1021/acsami.7b19740
M3 - Article
C2 - 29313658
AN - SCOPUS:85041928859
SN - 1944-8244
VL - 10
SP - 5114
EP - 5124
JO - ACS Applied Materials & Interfaces
JF - ACS Applied Materials & Interfaces
IS - 5
ER -