Pillararenes: fascinating cyclophanes with a bright future
Cragg, P.J. and Sharma, K. (2012) Pillararenes: fascinating cyclophanes with a bright future Chemical Society Reviews, 41 (2). pp. 597-607. ISSN 0306-0012
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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