Cragg, P.J. and Sharma, K.
Pillararenes: fascinating cyclophanes with a bright future
Chemical Society Reviews, 41 (2).
- Published Version
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Pillararenes are paracyclophane derivatives consisting of 1,4-disubstituted hydroquinones
linked by methylene bridges in the 2,5-positions. The first report of these novel macrocycles was
in 2008, when 1,4-dimethoxypillararene was prepared in 22% yield, and subsequent
improvements in synthetic methods have allowed the number of derivatives to expand
significantly. In addition to D5 symmetric pillararenes, asymmetric pillararenes with two
different substituents in the 1- and 4-positions and copillararenes consisting of two different
repeat units in a 4 : 1 ratio have been synthesised. Crystallographic, computational and
spectroscopic studies are starting to shed light on the compounds’ unusual inclusion phenomena,
from gelation and transportation of water through nanotubes to the formation of chromogenic
rotaxanes. Applications as molecular sensors are starting to appear with a focus on guest
detection by fluorescence quenching. This tutorial review will provide a summary of research into
the pillararenes since their recent discovery.
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