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|Title: ||Synthesis of mechanically interlocked oligomacrocyclic systems|
|Authors: ||Kroll, Marius Matthias|
|Supervisor(s): ||Leigh, David|
|Issue Date: ||2011|
|Publisher: ||The University of Edinburgh|
|Abstract: ||This thesis presents a modular palladium(II) template-directed synthetic strategy
towards mechanically interlocked polymacrocyclic architectures, such as a Borromean
link and linear [n]-catenanes. Central to the synthetic strategy is the use
of the Huisgen-Meldal-Sharpless Cu(I)-catalysed 1,3-cycloaddition of azides to
terminal alkynes (CuAAC) as a ring-closure procedure between complementary
pairs of building blocks. The amalgamation of the palladium(II) [3+1]-template
and CuAAC reaction is without methodological precedent and represents both an
efficient and versatile procedure for the construction of interlocked architectures.
Thematically, this thesis consists of three parts arranged in chronological order.
Beginning with the synthesis towards a Borromean link, where the first
successful palladium(II) template-directed double CuAAC ring-closure is documented.
This is followed by the application of the “double-click” strategy to
form a catenane - the first such structure generated using metal ions other
than Cu(I). Finally, the development of a modular CuAAC building block library
is described, which was used to construct a catenane and catenane as well
as later developments towards higher oligocatenanes.|
|Keywords: ||template chemistry|
|Appears in Collections:||Chemistry thesis and dissertation collection|
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