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The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement
Author(s) -
Kopilevich Sivil,
Gottlieb Hugo,
KeinanAdamsky Keren,
Müller Achim,
Weinstock Ira A.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201511341
Subject(s) - alkyl , chemistry , methylene , alkane , propionate , capsule , shell (structure) , hydrophobic effect , molecule , crystallography , stereochemistry , organic chemistry , materials science , hydrocarbon , botany , biology , composite material
In Nature, enzymes provide hydrophobic cavities and channels for sequestering small alkanes or long‐chain alkyl groups from water. Similarly, the porous metal oxide capsule [{Mo VI 6 O 21 (H 2 O) 6 } 12 {(Mo V 2 O 4 ) 30 (L) 29 (H 2 O) 2 }] 41− (L=propionate ligand) features distinct domains for sequestering differently sized alkanes (as in Nature) as well as internal dimensions suitable for multi‐alkane clustering. The ethyl tails of the 29 endohedrally coordinated ligands, L, form a spherical, hydrophobic “shell”, while their methyl end groups generate a hydrophobic cavity with a diameter of 11 Å at the center of the capsule. As such, C 7 to C 3 straight‐chain alkanes are tightly intercalated between the ethyl tails, giving assemblies containing 90 to 110 methyl and methylene units, whereas two or three ethane molecules reside in the central cavity of the capsule, where they are free to rotate rapidly, a phenomenon never before observed for the uptake of alkanes from water by molecular cages or containers.