The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement
Kopilevich S, Gottlieb H, Keinan-Adamsky K, Müller A, Weinstock IA (2016)
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55(14): 4476-4481.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Kopilevich, Sivil;
Gottlieb, Hugo;
Keinan-Adamsky, Keren;
Müller, AchimUniBi
;
Weinstock, Ira A.
![](https://pub.uni-bielefeld.de/images/icon_orcid.png)
Einrichtung
Abstract / Bemerkung
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 [{(Mo6O21)-O-VI(H2O)(6)}(12){((Mo2O4)-O-V)(30)(L)(29)(H2O)(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 angstrom 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.
Stichworte
alkanes;
confinement effect;
hydrophobicity;
molybdenum;
porous capsules
Erscheinungsjahr
2016
Zeitschriftentitel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Band
55
Ausgabe
14
Seite(n)
4476-4481
ISSN
1433-7851
eISSN
1521-3773
Page URI
https://pub.uni-bielefeld.de/record/2903039
Zitieren
Kopilevich S, Gottlieb H, Keinan-Adamsky K, Müller A, Weinstock IA. The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2016;55(14):4476-4481.
Kopilevich, S., Gottlieb, H., Keinan-Adamsky, K., Müller, A., & Weinstock, I. A. (2016). The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 55(14), 4476-4481. doi:10.1002/anie.201511341
Kopilevich, Sivil, Gottlieb, Hugo, Keinan-Adamsky, Keren, Müller, Achim, and Weinstock, Ira A. 2016. “The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55 (14): 4476-4481.
Kopilevich, S., Gottlieb, H., Keinan-Adamsky, K., Müller, A., and Weinstock, I. A. (2016). The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55, 4476-4481.
Kopilevich, S., et al., 2016. The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 55(14), p 4476-4481.
S. Kopilevich, et al., “The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement”, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 55, 2016, pp. 4476-4481.
Kopilevich, S., Gottlieb, H., Keinan-Adamsky, K., Müller, A., Weinstock, I.A.: The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 55, 4476-4481 (2016).
Kopilevich, Sivil, Gottlieb, Hugo, Keinan-Adamsky, Keren, Müller, Achim, and Weinstock, Ira A. “The Uptake and Assembly of Alkanes within a Porous Nanocapsule in Water: New Information about Hydrophobic Confinement”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55.14 (2016): 4476-4481.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
6 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Host-guest chemistry with water-soluble gold nanoparticle supraspheres.
Wang Y, Zeiri O, Raula M, Le Ouay B, Stellacci F, Weinstock IA., Nat Nanotechnol 12(2), 2017
PMID: 27842065
Wang Y, Zeiri O, Raula M, Le Ouay B, Stellacci F, Weinstock IA., Nat Nanotechnol 12(2), 2017
PMID: 27842065
Anions coordinating anions: analysis of the interaction between anionic Keplerate nanocapsules and their anionic ligands.
Melgar D, Bandeira NA, Bonet Avalos J, Bo C., Phys Chem Chem Phys 19(7), 2017
PMID: 28155941
Melgar D, Bandeira NA, Bonet Avalos J, Bo C., Phys Chem Chem Phys 19(7), 2017
PMID: 28155941
Structurally Stable Attractive Nanoscale Emulsions with Dipole-Dipole Interaction-Driven Interdrop Percolation.
Shin K, Gong G, Cuadrado J, Jeon S, Seo M, Choi HS, Hwang JS, Lee Y, Fernandez-Nieves A, Kim JW., Chemistry 23(18), 2017
PMID: 28102556
Shin K, Gong G, Cuadrado J, Jeon S, Seo M, Choi HS, Hwang JS, Lee Y, Fernandez-Nieves A, Kim JW., Chemistry 23(18), 2017
PMID: 28102556
Polyoxometalate-Engineered Building Blocks with Gold Cores for the Self-Assembly of Responsive Water-Soluble Nanostructures.
Wang Y, Raula M, Wang Y, Zeiri O, Chakraborty S, Gan-Or G, Gadot E, Weinstock IA., Angew Chem Int Ed Engl 56(25), 2017
PMID: 28508392
Wang Y, Raula M, Wang Y, Zeiri O, Chakraborty S, Gan-Or G, Gadot E, Weinstock IA., Angew Chem Int Ed Engl 56(25), 2017
PMID: 28508392
Densely Packed Hydrophobic Clustering: Encapsulated Valerates Form a High-Temperature-Stable {Mo132 } Capsule System.
Garai S, Bögge H, Merca A, Petina OA, Grego A, Gouzerh P, Haupt ET, Weinstock IA, Müller A., Angew Chem Int Ed Engl 55(23), 2016
PMID: 27140207
Garai S, Bögge H, Merca A, Petina OA, Grego A, Gouzerh P, Haupt ET, Weinstock IA, Müller A., Angew Chem Int Ed Engl 55(23), 2016
PMID: 27140207
Encapsulation of Arenes within a Porous Molybdenum Oxide {Mo132 } Nanocapsule.
Sarma BB, Avram L, Neumann R., Chemistry 22(43), 2016
PMID: 27576915
Sarma BB, Avram L, Neumann R., Chemistry 22(43), 2016
PMID: 27576915
77 References
Daten bereitgestellt von Europe PubMed Central.
AUTHOR UNKNOWN, 0
Carroll, 2009
Sloan, 2007
AUTHOR UNKNOWN, 2003
AUTHOR UNKNOWN, 0
Coupling Oxygen Consumption with Hydrocarbon Oxidation in Bacterial Multicomponent Monooxygenases.
Wang W, Liang AD, Lippard SJ., Acc. Chem. Res. 48(9), 2015
PMID: 26293615
Wang W, Liang AD, Lippard SJ., Acc. Chem. Res. 48(9), 2015
PMID: 26293615
Enzymatic oxidation of methane.
Sirajuddin S, Rosenzweig AC., Biochemistry 54(14), 2015
PMID: 25806595
Sirajuddin S, Rosenzweig AC., Biochemistry 54(14), 2015
PMID: 25806595
Hydrocarbon binding by proteins: structures of protein binding sites for ≥C10 linear alkanes or long-chain alkyl and alkenyl groups.
Park J, Pham HV, Mogensen K, Solling TI, Bennetzen MV, Houk KN., J. Org. Chem. 80(2), 2015
PMID: 25526284
Park J, Pham HV, Mogensen K, Solling TI, Bennetzen MV, Houk KN., J. Org. Chem. 80(2), 2015
PMID: 25526284
AUTHOR UNKNOWN, 0
NMR investigation of chloromethane complexes of cryptophane-A and its analogue with butoxy groups.
Takacs Z, Steiner E, Kowalewski J, Brotin T., J Phys Chem B 118(8), 2014
PMID: 24472055
Takacs Z, Steiner E, Kowalewski J, Brotin T., J Phys Chem B 118(8), 2014
PMID: 24472055
Unique organization of solvent molecules within the hexameric capsules of pyrogallol[4]arene in solution.
Guralnik V, Avram L, Cohen Y., Org. Lett. 16(21), 2014
PMID: 25337806
Guralnik V, Avram L, Cohen Y., Org. Lett. 16(21), 2014
PMID: 25337806
Recent advances in hydrogen-bonded hexameric encapsulation complexes.
Avram L, Cohen Y, Rebek J Jr., Chem. Commun. (Camb.) 47(19), 2011
PMID: 21431233
Avram L, Cohen Y, Rebek J Jr., Chem. Commun. (Camb.) 47(19), 2011
PMID: 21431233
Molecules at close range: encapsulated solvent molecules in pyrogallol[4]arene hexameric capsules.
Avram L, Cohen Y., Org. Lett. 8(2), 2006
PMID: 16408879
Avram L, Cohen Y., Org. Lett. 8(2), 2006
PMID: 16408879
Garel, Angew. Chem. Int. Ed. Engl. 32(), 1993
AUTHOR UNKNOWN, Angew. Chem. 105(), 1993
Carbon dioxide fixation and sulfate sequestration by a supramolecular trigonal bipyramid.
Browne C, Ramsay WJ, Ronson TK, Medley-Hallam J, Nitschke JR., Angew. Chem. Int. Ed. Engl. 54(38), 2015
PMID: 26235039
Browne C, Ramsay WJ, Ronson TK, Medley-Hallam J, Nitschke JR., Angew. Chem. Int. Ed. Engl. 54(38), 2015
PMID: 26235039
AUTHOR UNKNOWN, Angew. Chem. 127(), 2015
Molecules within molecules: recognition through self-assembly.
Hof F, Rebek J Jr., Proc. Natl. Acad. Sci. U.S.A. 99(8), 2002
PMID: 11880604
Hof F, Rebek J Jr., Proc. Natl. Acad. Sci. U.S.A. 99(8), 2002
PMID: 11880604
Helical folding of alkanes in a self-assembled, cylindrical capsule.
Scarso A, Trembleau L, Rebek J Jr., J. Am. Chem. Soc. 126(41), 2004
PMID: 15479107
Scarso A, Trembleau L, Rebek J Jr., J. Am. Chem. Soc. 126(41), 2004
PMID: 15479107
Water-soluble, self-assembling container molecules: an update.
Laughrey Z, Gibb BC., Chem Soc Rev 40(1), 2010
PMID: 21076776
Laughrey Z, Gibb BC., Chem Soc Rev 40(1), 2010
PMID: 21076776
Guest packing motifs within a supramolecular nanocapsule and a covalent analogue.
Liu S, Russell DH, Zinnel NF, Gibb BC., J. Am. Chem. Soc. 135(11), 2013
PMID: 23448338
Liu S, Russell DH, Zinnel NF, Gibb BC., J. Am. Chem. Soc. 135(11), 2013
PMID: 23448338
Nonmonotonic assembly of a deep-cavity cavitand.
Gan H, Benjamin CJ, Gibb BC., J. Am. Chem. Soc. 133(13), 2011
PMID: 21401093
Gan H, Benjamin CJ, Gibb BC., J. Am. Chem. Soc. 133(13), 2011
PMID: 21401093
AUTHOR UNKNOWN, 0
Dual-cavity basket promotes encapsulation in water in an allosteric fashion.
Chen S, Yamasaki M, Polen S, Gallucci J, Hadad CM, Badjic JD., J. Am. Chem. Soc. 137(38), 2015
PMID: 26348904
Chen S, Yamasaki M, Polen S, Gallucci J, Hadad CM, Badjic JD., J. Am. Chem. Soc. 137(38), 2015
PMID: 26348904
On the encapsulation of hydrocarbon components of natural gas within molecular baskets in water. The role of C-H···π interactions and the host's conformational dynamics in the process of encapsulation.
Ruan Y, Peterson PW, Hadad CM, Badjic JD., Chem. Commun. (Camb.) 50(65), 2014
PMID: 24986237
Ruan Y, Peterson PW, Hadad CM, Badjic JD., Chem. Commun. (Camb.) 50(65), 2014
PMID: 24986237
Solvent effects upon guest binding and dynamics of a Fe(II)4L4 cage.
Bolliger JL, Ronson TK, Ogawa M, Nitschke JR., J. Am. Chem. Soc. 136(41), 2014
PMID: 25226369
Bolliger JL, Ronson TK, Ogawa M, Nitschke JR., J. Am. Chem. Soc. 136(41), 2014
PMID: 25226369
AUTHOR UNKNOWN, 0
Smithrud, J. Am. Chem. Soc. 113(), 1991
Smithrud, J. Am. Chem. Soc. 112(), 1990
AUTHOR UNKNOWN, 0
Nau, Isr. J. Chem. 51(), 2011
Strong binding of hydrocarbons to cucurbituril probed by fluorescent dye displacement: a supramolecular gas-sensing ensemble.
Florea M, Nau WM., Angew. Chem. Int. Ed. Engl. 50(40), 2011
PMID: 21948429
Florea M, Nau WM., Angew. Chem. Int. Ed. Engl. 50(40), 2011
PMID: 21948429
AUTHOR UNKNOWN, Angew. Chem. 123(), 2011
"Molecular" molecular sieves: lid-free decamethylcucurbit[5]uril absorbs and desorbs gases selectively.
Miyahara Y, Abe K, Inazu T., Angew. Chem. Int. Ed. Engl. 41(16), 2002
PMID: 12203444
Miyahara Y, Abe K, Inazu T., Angew. Chem. Int. Ed. Engl. 41(16), 2002
PMID: 12203444
AUTHOR UNKNOWN, Angew. Chem. 114(), 2002
U-shaped conformation of alkyl chains bound to a synthetic host.
Ko YH, Kim H, Kim Y, Kim K., Angew. Chem. Int. Ed. Engl. 47(22), 2008
PMID: 18442155
Ko YH, Kim H, Kim Y, Kim K., Angew. Chem. Int. Ed. Engl. 47(22), 2008
PMID: 18442155
AUTHOR UNKNOWN, Angew. Chem. 120(), 2008
AUTHOR UNKNOWN, 0
Tanford, 1980
Nelson, 2008
Dispersive interactions in solution complexes.
Schneider HJ., Acc. Chem. Res. 48(7), 2015
PMID: 26083908
Schneider HJ., Acc. Chem. Res. 48(7), 2015
PMID: 26083908
The hydrophobic effect revisited--studies with supramolecular complexes imply high-energy water as a noncovalent driving force.
Biedermann F, Nau WM, Schneider HJ., Angew. Chem. Int. Ed. Engl. 53(42), 2014
PMID: 25070083
Biedermann F, Nau WM, Schneider HJ., Angew. Chem. Int. Ed. Engl. 53(42), 2014
PMID: 25070083
AUTHOR UNKNOWN, Angew. Chem. 126(), 2014
Water repellency in hydrophobic nanocapsules--molecular view on dewetting.
Muller A, Garai S, Schaffer C, Merca A, Bogge H, Al-Karawi AJ, Prasad TK., Chemistry 20(22), 2014
PMID: 24782303
Muller A, Garai S, Schaffer C, Merca A, Bogge H, Al-Karawi AJ, Prasad TK., Chemistry 20(22), 2014
PMID: 24782303
Blokzijl, Angew. Chem. Int. Ed. Engl. 32(), 1993
AUTHOR UNKNOWN, Angew. Chem. 105(), 1993
AUTHOR UNKNOWN, 0
Amplified Rate Acceleration by Simultaneous Up-Regulation of Multiple Active Sites in an Endo-Functionalized Porous Capsule.
Kopilevich S, Muller A, Weinstock IA., J. Am. Chem. Soc. 137(40), 2015
PMID: 26354143
Kopilevich S, Muller A, Weinstock IA., J. Am. Chem. Soc. 137(40), 2015
PMID: 26354143
Catalysis in a porous molecular capsule: activation by regulated access to sixty metal centers spanning a truncated icosahedron.
Kopilevich S, Gil A, Garcia-Rates M, Bonet-Avalos J, Bo C, Muller A, Weinstock IA., J. Am. Chem. Soc. 134(31), 2012
PMID: 22765884
Kopilevich S, Gil A, Garcia-Rates M, Bonet-Avalos J, Bo C, Muller A, Weinstock IA., J. Am. Chem. Soc. 134(31), 2012
PMID: 22765884
Flexible pores of a metal oxide-based capsule permit entry of comparatively larger organic guests.
Ziv A, Grego A, Kopilevich S, Zeiri L, Miro P, Bo C, Muller A, Weinstock IA., J. Am. Chem. Soc. 131(18), 2009
PMID: 19290673
Ziv A, Grego A, Kopilevich S, Zeiri L, Miro P, Bo C, Muller A, Weinstock IA., J. Am. Chem. Soc. 131(18), 2009
PMID: 19290673
Hydrophobic effect as a driving force for host-guest chemistry of a multi-receptor Keplerate-type capsule.
Watfa N, Melgar D, Haouas M, Taulelle F, Hijazi A, Naoufal D, Avalos JB, Floquet S, Bo C, Cadot E., J. Am. Chem. Soc. 137(17), 2015
PMID: 25870906
Watfa N, Melgar D, Haouas M, Taulelle F, Hijazi A, Naoufal D, Avalos JB, Floquet S, Bo C, Cadot E., J. Am. Chem. Soc. 137(17), 2015
PMID: 25870906
AUTHOR UNKNOWN, 0
Capsules with highly active pores and interiors: versatile platforms at the nanoscale.
Muller A, Gouzerh P., Chemistry 20(17), 2014
PMID: 24644235
Muller A, Gouzerh P., Chemistry 20(17), 2014
PMID: 24644235
From linking of metal-oxide building blocks in a dynamic library to giant clusters with unique properties and towards adaptive chemistry.
Muller A, Gouzerh P., Chem Soc Rev 41(22), 2012
PMID: 22948798
Muller A, Gouzerh P., Chem Soc Rev 41(22), 2012
PMID: 22948798
Stepwise-resolved thermodynamics of hydrophobic self-assembly.
Grego A, Muller A, Weinstock IA., Angew. Chem. Int. Ed. Engl. 52(32), 2013
PMID: 23765614
Grego A, Muller A, Weinstock IA., Angew. Chem. Int. Ed. Engl. 52(32), 2013
PMID: 23765614
AUTHOR UNKNOWN, Angew. Chem. 125(), 2013
Hydrophobic interactions and clustering in a porous capsule: option to remove hydrophobic materials from water.
Schaffer C, Todea AM, Bogge H, Petina OA, Rehder D, Haupt ET, Muller A., Chemistry 17(35), 2011
PMID: 21748814
Schaffer C, Todea AM, Bogge H, Petina OA, Rehder D, Haupt ET, Muller A., Chemistry 17(35), 2011
PMID: 21748814
A spherical 24 butyrate aggregate with a hydrophobic cavity in a capsule with flexible pores: confinement effects and uptake-release equilibria at elevated temperatures.
Schaffer C, Bogge H, Merca A, Weinstock IA, Rehder D, Haupt ET, Muller A., Angew. Chem. Int. Ed. Engl. 48(43), 2009
PMID: 19774583
Schaffer C, Bogge H, Merca A, Weinstock IA, Rehder D, Haupt ET, Muller A., Angew. Chem. Int. Ed. Engl. 48(43), 2009
PMID: 19774583
AUTHOR UNKNOWN, Angew. Chem. 121(), 2009
AUTHOR UNKNOWN, 0
Johnson, Prog. Nucl. Magn. Reson. Spectrosc. 34(), 1999
Friebolin, 2010
AUTHOR UNKNOWN, 0
Bondi, J. Phys. Chem. 68(), 1964
AUTHOR UNKNOWN, 0
Mecozzi, Chem. Eur. J. 4(), 1998
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Guests on different internal capsule sites exchange with each other and with the outside.
Petina O, Rehder D, Haupt ET, Grego A, Weinstock IA, Merca A, Bogge H, Szakacs J, Muller A., Angew. Chem. Int. Ed. Engl. 50(2), 2011
PMID: 21132826
Petina O, Rehder D, Haupt ET, Grego A, Weinstock IA, Merca A, Bogge H, Szakacs J, Muller A., Angew. Chem. Int. Ed. Engl. 50(2), 2011
PMID: 21132826
AUTHOR UNKNOWN, Angew. Chem. 123(), 2011
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Fundamental principles and applications of natural gas hydrates.
Sloan ED Jr., Nature 426(6964), 2003
PMID: 14628065
Sloan ED Jr., Nature 426(6964), 2003
PMID: 14628065
Davidson, J. Incl. Phen. 2(), 1984
AUTHOR UNKNOWN, 0
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 26880403
PubMed | Europe PMC
Suchen in