Template-Directed Syntheses of Catenanes

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Title:Template-Directed Syntheses of Catenanes
Creators:
Bělohradský, Martin
Raymo, Françisco M.
Stoddart, J. Fraser
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 4, pp. 527-557
Uncontrolled Keywords:Template-directed synthesis, Self-assembly, Catenanes

Abstract

The art and science of introducing mechanical-interlocking at the molecular level in order to generate catenanes - molecules composed of two or more macrocyclic components - offers the opportunity of constructing a new range of molecular compounds possessing intriguing properties. However, the topological features displayed by catenanes has rendered the syntheses of such molecular compounds an extremely challenging task for synthetic chemists to address. Their early syntheses were based upon either statistical approaches - the threading of a small amount of a macrocycle on to an acyclic precursor as a chance event - or directed approaches, relying upon the temporary introduction of covalent bonds in the multistep synthesis of a so-called precatenane, followed by its conversion ultimately into a catenane. These approaches afforded catenanes in very low yields overall and only after following tedious and laborious synthetic procedures. Fortunately, however, with the advent of supramolecular chemistry, template-directed methods that allow us to self-assemble [<i>n</i>]catenanes much more efficiently have become available. Numerous successful template-directed syntheses have now emerged - some by chance and others by design. These methods have been based upon (i) metal coordinating, (ii) hydrogen bonding, (iii) solvophobic, and/or (iv) π-π stacking interactions which have been found to govern self-assembly processes to catenated compounds from appropriate precursors. Their relative simplicity, the high degree of control with which they can be employed, and the remarkable efficiency with which they proceed has already provided the opportunity to synthetic chemists to self-assemble a series of [<i>n</i>]catenanes, incorporating from two up to five mechanically-interlocked macrocyclic components.

Title:Template-Directed Syntheses of Catenanes
Creators:
Bělohradský, Martin
Raymo, Françisco M.
Stoddart, J. Fraser
Uncontrolled Keywords:Template-directed synthesis, Self-assembly, Catenanes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:4
Page Range:pp. 527-557
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19970527UNSPECIFIED
ID Code:1138
Item Type:Article
Deposited On:06 Feb 2009 17:07
Last Modified:06 Feb 2009 16:07

Citation

Bělohradský, Martin; Raymo, Françisco M.; Stoddart, J. Fraser (1997) Template-Directed Syntheses of Catenanes. Collection of Czechoslovak Chemical Communications, 62 (4). pp. 527-557. ISSN 0010-0765

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