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Catenane information


Crystal structure of a catenane with a cyclobis(paraquat-p-phenylene) macrocycle reported by Stoddart and coworkers.[1]
Schematic animation of the template-directed synthesis of the bis-bipyridinium cyclophane / para-phenylene crown ether [2]catenane described in the text.
Crystal structure of a catenane reported by Sauvage and coworkers.[2]

In macromolecular chemistry, a catenane (from Latin catena 'chain') 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. 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.

  1. ^ Ashton, Peter R.; Brown, Christopher L.; Chrystal, Ewan J. T.; Goodnow, Timothy T.; Kaifer, Angel E.; Parry, Keith P.; Philp, Douglas; Slawin, Alexandra M. Z.; Spencer, Neil; Stoddart, J. Fraser; Williams, David J. (1991). "The self-assembly of a highly ordered [2]catenane". Journal of the Chemical Society, Chemical Communications (9): 634. doi:10.1039/C39910000634.
  2. ^ Cesario, M.; Dietrich-Buchecker, C. O.; Guilhem, J.; Pascard, C.; Sauvage, J. P. (1985). "Molecular structure of a catenand and its copper(I) catenate: complete rearrangement of the interlocked macrocyclic ligands by complexation". Journal of the Chemical Society, Chemical Communications (5): 244. doi:10.1039/C39850000244.

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Catenane

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In macromolecular chemistry, a catenane (from Latin catena 'chain') is a mechanically interlocked molecular architecture consisting of two or more interlocked...

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Topoisomer

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which there exist topoisomers include DNA, which can form knots, and catenanes. Each topoisomer of a given DNA molecule possesses a different linking...

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Polycatenane

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linked catenane structures, via topological Hopf links, resulting in a higher dimensionality than the repeating unit. They are a class of catenanes where...

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Molecular knot

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al. in 2000 to describe molecular knots by analogy with rotaxanes and catenanes, which are other mechanically interlocked molecular architectures. The...

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Crown ether

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Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. (1989). "A [2] Catenane Made to Order". Angewandte Chemie International Edition in English. 28...

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Olympiadane

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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...

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Molecular switch

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delivers a switchable molecule based not on a rotaxane but on a related catenane This compound is based on two ring systems: one ring holds the photoswichable...

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Rotaxane

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rotaxanes and other mechanically interlocked molecular architectures, such as catenanes, has been focused on their efficient synthesis or their utilization as...

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Molecular Borromean rings

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differs from a [3]catenane in that none of its three macrocycles is concatenated with another other; if one bond in a [3]catenane is broken and a cycle...

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Molecular machine

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Building upon the assembly of mechanically linked molecules such as catenanes and rotaxanes as developed by Jean-Pierre Sauvage in the early 1980s,...

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Mechanically interlocked molecular architectures

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Examples of mechanically interlocked molecular architectures include catenanes, rotaxanes, molecular knots, and molecular Borromean rings. Work in this...

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Grid complex

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complex has been used to template the synthesis of a doubly-twisted [2]catenane (otherwise known as a Solomon Link). The unique arrangement of interwoven...

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Cyclodextrin

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mechanically interlocked molecular architectures, such as rotaxanes and catenanes. Illustrative, α-cyclodextrin form second-sphere coordination complex...

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Isomer

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topoisomers. Also, two or more such molecules may be bound together in a catenane by such topological linkages, even if there is no chemical bond between...

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Topoisomerase

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rise to tertiary conformations of DNA, such as supercoils, knots and catenanes. Potential topological issues associated with the double-helical structure...

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Macrocycle

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often bioactive and could be useful for drug delivery. Cryptand Rotaxane Catenane Molecular knot Effective molarity Macrocyclic stereocontrol Macrocyclic...

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Hopf link

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founded in the 16th century. Borromean rings, a link with three closed loops Catenane, a molecule with two linked loops Solomon's knot, two loops which are doubly...

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Click chemistry

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triazole ligation supramolecular chemistry: calixarenes, rotaxanes, and catenanes dendrimer design carbohydrate clusters and carbohydrate conjugation by...

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Fraser Stoddart

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mechanically-interlocked molecular architectures such as molecular Borromean rings, catenanes and rotaxanes utilising molecular recognition and molecular self-assembly...

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Guillaume De Bo

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showed how the ability of the two rings in [2]catenane to rotate alone each other enables [2]catenane to be used as a mechanical protecting group via...

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Alexandra Slawin

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understand the structure of supramolecular systems (e.g. rotaxanes and catenanes). She is generally considered as one of the world's leading crystallographers...

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Topoisomerase IV

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Topoisomerase IV can unknot right-handed knots and decatenate right-handed catenanes without acting on right-handed plectonemes in negatively supercoiled DNA...

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Topoisomerase inhibitor

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cleavage of single and double stranded DNA to relax supercoils, untangle catenanes, and condense chromosomes in eukaryotic cells. Topoisomerase inhibitors...

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Circular chromosome

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opposing replication forks, leaves the completed chromosomes joined as ‘catenanes’ or topologically interlinked circles. The circles are not covalently...

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