Olympiadane

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Olympiadane
Olympiadane.svg
Olympiadane ions spacefill.png
Names
IUPAC name
6,9,12,15,18,29,32,35,38,41,52,55,58,61,64-pentadecaoxaheptacyclo[63.4.0.05,69.019,24.023,28.042,47.046,51]nonahexaconta-1(69),2,4,19,21,23,25,27,42,44,46,48,50,65,67-pentadecaene;5,12,19,26-tetrazoniaheptacyclo[24.2.2.22,5.27,10.212,15.216,19.221,24]tetraconta-1(29),2(40),3,5(39),7,9,12,14,16(34),17,19(33),21(32),22,24(31),26(30),27,35,37-octadecaene;dodecahexafluorophosphate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/2C54H66O15.3C36H32N4.12F6P/c2*1-7-43-44-8-2-14-50(43)65-38-32-59-26-20-56-22-28-61-34-40-67-52-16-5-12-48-47(52)11-6-18-54(48)69-42-36-63-30-24-57-23-29-62-35-41-68-53-17-4-9-45-46(53)10-3-15-51(45)66-39-33-60-27-21-55-19-25-58-31-37-64-49(44)13-1;3*1-2-30-4-3-29(1)25-37-17-9-33(10-18-37)35-13-21-39(22-14-35)27-31-5-7-32(8-6-31)28-40-23-15-36(16-24-40)34-11-19-38(26-30)20-12-34;12*1-7(2,3,4,5)6/h2*1-18H,19-42H2;3*1-24H,25-28H2;;;;;;;;;;;;/q;;3*+4;12*-1
    Key: ROLRJLKBOAVDIY-UHFFFAOYSA-N
  • c1cc2c3cccc2OCCOCCOCCOCCOc4cccc5c4cccc5OCCOCCOCCOCCOc6cccc7c6cccc7OCCOCCOCCOCCOc3c1.c1cc2c3cccc2OCCOCCOCCOCCOc4cccc5c4cccc5OCCOCCOCCOCCOc6cccc7c6cccc7OCCOCCOCCOCCOc3c1.c1cc2ccc1C[n+]3ccc(cc3)-c4cc[n+](cc4)Cc5ccc(cc5)C[n+]6ccc(cc6)-c7cc[n+](cc7)C2.c1cc2ccc1C[n+]3ccc(cc3)-c4cc[n+](cc4)Cc5ccc(cc5)C[n+]6ccc(cc6)-c7cc[n+](cc7)C2.c1cc2ccc1C[n+]3ccc(cc3)-c4cc[n+](cc4)Cc5ccc(cc5)C[n+]6ccc(cc6)-c7cc[n+](cc7)C2.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F
Properties
C228H236F72N12O30P12
Molar mass 5364.020 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Olympiadane is a mechanically interlocked molecule composed of five interlocking macrocycles that resembles the Olympic rings. The molecule is a linear pentacatenane or a [5]catenane. It was synthesized and named by Fraser Stoddart and coworkers in 1994. [1] The molecule was designed without any practical use in mind, [2] although other catenanes may have possible application to the construction of a molecular computer.

See also

Related Research Articles

<span class="mw-page-title-main">Rotaxane</span> Interlocked molecular structure

A rotaxane is a mechanically interlocked molecular architecture consisting of a "dumbbell shaped molecule" which is threaded through a "macrocycle". The name is derived from the Latin for wheel (rota) and axle (axis). The two components of a rotaxane are kinetically trapped since the ends of the dumbbell are larger than the internal diameter of the ring and prevent dissociation (unthreading) of the components since this would require significant distortion of the covalent bonds.

Supramolecular chemistry refers to the branch of chemistry concerning chemical systems composed of a discrete number of molecules. The strength of the forces responsible for spatial organization of the system range from weak intermolecular forces, electrostatic charge, or hydrogen bonding to strong covalent bonding, provided that the electronic coupling strength remains small relative to the energy parameters of the component. While traditional chemistry concentrates on the covalent bond, supramolecular chemistry examines the weaker and reversible non-covalent interactions between molecules. These forces include hydrogen bonding, metal coordination, hydrophobic forces, van der Waals forces, pi–pi interactions and electrostatic effects.

<span class="mw-page-title-main">Catenane</span>

A catenane is a mechanically interlocked molecular architecture consisting of two or more interlocked macrocycles, i.e. a molecule containing two or more intertwined rings. The interlocked rings cannot be separated without breaking the covalent bonds of the macrocycles. Catenane is derived from the Latin catena meaning "chain". They are conceptually related to other mechanically interlocked molecular architectures, such as rotaxanes, molecular knots or molecular Borromean rings. Recently the terminology "mechanical bond" has been coined that describes the connection between the macrocycles of a catenane. Catenanes have been synthesised in two different ways: statistical synthesis and template-directed synthesis.

<span class="mw-page-title-main">Topoisomer</span>

Topoisomers or topological isomers are molecules with the same chemical formula and stereochemical bond connectivities but different topologies. Examples of molecules for which there exist topoisomers include DNA, which can form knots, and catenanes. Each topoisomer of a given DNA molecule possesses a different linking number associated with it. DNA topoisomers can be interchanged by enzymes called topoisomerases. Using a topoisomerase along with an intercalator, topoisomers with different linking number may be separated on an agarose gel via gel electrophoresis.

Interlock can refer to the following:

<span class="mw-page-title-main">Molecular machine</span> Molecular-scale artificial or biological device

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<span class="mw-page-title-main">Macrocycle</span> Molecule with a large ring structure

Macrocycles are often described as molecules and ions containing a ring of twelve or more atoms. Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins. Macrocycles describe a large, mature area of chemistry.

<span class="mw-page-title-main">Molecular Borromean rings</span>

Molecular Borromean rings are an example of a mechanically-interlocked molecular architecture in which three macrocycles are interlocked in such a way that breaking any macrocycle allows the others to disassociate. They are the smallest examples of Borromean rings. The synthesis of molecular Borromean rings was reported in 2004 by the group of J. Fraser Stoddart. The so-called Borromeate is made up of three interpenetrated macrocycles formed through templated self assembly as complexes of zinc.

<span class="mw-page-title-main">Fraser Stoddart</span> Scottish chemist and 2016 Nobel Laureate

Sir James Fraser Stoddart is a British-American chemist who is Board of Trustees Professor of Chemistry and head of the Stoddart Mechanostereochemistry Group in the Department of Chemistry at Northwestern University in the United States. He works in the area of supramolecular chemistry and nanotechnology. Stoddart has developed highly efficient syntheses of mechanically-interlocked molecular architectures such as molecular Borromean rings, catenanes and rotaxanes utilising molecular recognition and molecular self-assembly processes. He has demonstrated that these topologies can be employed as molecular switches. His group has even applied these structures in the fabrication of nanoelectronic devices and nanoelectromechanical systems (NEMS). His efforts have been recognized by numerous awards including the 2007 King Faisal International Prize in Science. He shared the Nobel Prize in Chemistry together with Ben Feringa and Jean-Pierre Sauvage in 2016 for the design and synthesis of molecular machines.

<span class="mw-page-title-main">Pi-Stacking (chemistry)</span> Attractive interactions between aromatic rings

In chemistry, pi stacking refers to the presumptive attractive, noncovalent interactions between the pi bonds of aromatic rings. However this is a misleading description of the phenomena since direct stacking of aromatic rings is electrostatically repulsive. What is more commonly observed is either a staggered stacking or pi-teeing interaction both of which are electrostatic attractive For example, the most commonly observed interactions between aromatic rings of amino acid residues in proteins is a staggered stacked followed by a perpendicular orientation. Sandwiched orientations are relatively rare.

<span class="mw-page-title-main">Jean-Pierre Sauvage</span> French chemist, Nobel laureate

Jean-Pierre Sauvage is a French coordination chemist working at Strasbourg University. He graduated from the National School of Chemistry of Strasbourg, in 1967. He has specialized in supramolecular chemistry for which he has been awarded the 2016 Nobel Prize in Chemistry along with Sir J. Fraser Stoddart and Bernard L. Feringa.

Mechanically interlocked molecular architectures (MIMAs) are molecules that are connected as a consequence of their topology. This connection of molecules is analogous to keys on a keychain loop. The keys are not directly connected to the keychain loop but they cannot be separated without breaking the loop. On the molecular level the interlocked molecules cannot be separated without the breaking of the covalent bonds that comprise the conjoined molecules, this is referred to as a mechanical bond. Examples of mechanically interlocked molecular architectures include catenanes, rotaxanes, molecular knots, and molecular Borromean rings. Work in this area was recognized with the 2016 Nobel Prize in Chemistry to Bernard L. Feringa, Jean-Pierre Sauvage, and J. Fraser Stoddart.

<span class="mw-page-title-main">Cation–π interaction</span>

Cation–π interaction is a noncovalent molecular interaction between the face of an electron-rich π system (e.g. benzene, ethylene, acetylene) and an adjacent cation (e.g. Li+, Na+). This interaction is an example of noncovalent bonding between a monopole (cation) and a quadrupole (π system). Bonding energies are significant, with solution-phase values falling within the same order of magnitude as hydrogen bonds and salt bridges. Similar to these other non-covalent bonds, cation–π interactions play an important role in nature, particularly in protein structure, molecular recognition and enzyme catalysis. The effect has also been observed and put to use in synthetic systems.

Residual topology is a descriptive stereochemical term to classify a number of intertwined and interlocked molecules, which cannot be disentangled in an experiment without breaking of covalent bonds, while the strict rules of mathematical topology allow such a disentanglement. Examples of such molecules are rotaxanes, catenanes with covalently linked rings, and open knots (pseudoknots) which are abundant in proteins.

<span class="mw-page-title-main">David Leigh (scientist)</span> British chemist

David Alan Leigh FRS FRSE FRSC is a British chemist, Royal Society Research Professor and, since 2014, the Sir Samuel Hall Chair of Chemistry in the Department of Chemistry at the University of Manchester. He was previously the Forbes Chair of Organic Chemistry at the University of Edinburgh (2001–2012) and Professor of Synthetic Chemistry at the University of Warwick (1998–2001).

A molecular switch is a molecule that can be reversibly shifted between two or more stable states. The molecules may be shifted between the states in response to environmental stimuli, such as changes in pH, light, temperature, an electric current, microenvironment, or in the presence of ions and other ligands. In some cases, a combination of stimuli is required. The oldest forms of synthetic molecular switches are pH indicators, which display distinct colors as a function of pH. Currently synthetic molecular switches are of interest in the field of nanotechnology for application in molecular computers or responsive drug delivery systems. Molecular switches are also important in biology because many biological functions are based on it, for instance allosteric regulation and vision. They are also one of the simplest examples of molecular machines.

<span class="mw-page-title-main">Olympicene</span> Chemical compound

Olympicene is an organic carbon based molecule formed of five rings, of which four are benzene rings, joined in the shape of the Olympic rings.

Cyclobis(paraquat-<i>p</i>-phenylene) Chemical compound

Cyclobis(paraquat-p-phenylene) belongs to the class of cyclophanes, and consists of aromatic units connected by methylene bridges. It is able to incorporate small guest molecule and has played an important role in host–guest chemistry and supramolecular chemistry.

Latticial metal complex or grid complex is a supramolecular complex of several metal atoms and coordinating ligands which form a grid-like structural motif. The structure formation usually occurs while on thermodynamic molecular self-assembly. They have properties that make them interesting for information technology as the future storage materials. Chelate ligands are used as ligands in tetrahedral or octahedral structures, which mostly use nitrogen atoms in pyridine like ring systems other than donor centers. Suitable metal ions are in accordance with octahedral coordinating transition metal ions such as Mn or rare tetrahedral Coordinating such as Ag used.

<span class="mw-page-title-main">Polyrotaxane</span>

Polyrotaxane is a type of mechanically interlocked molecule consisting of strings and rings, in which multiple rings are threaded onto a molecular axle and prevented from dethreading by two bulky end groups. As oligomeric or polymeric species of rotaxanes, polyrotaxanes are also capable of converting energy input to molecular movements because the ring motions can be controlled by external stimulus. Polyrotaxanes have attracted much attention for decades, because they can help build functional molecular machines with complicated molecular structure.

References

  1. ↑ Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F. (1994). "Olympiadane". Angew. Chem. Int. Ed. Engl. 33 (12): 1286–1290. doi:10.1002/anie.199412861.
  2. ↑ Browne, M. W. (30 August 1994). "Chemists Make Rings Of Interlocked Atoms, A Clue to Life's Origin". The New York Times . Retrieved 3 January 2016.
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