Pillar[5]arenes: fascinating cyclophanes with a bright future

Cragg, P.J. and Sharma, K. (2012) Pillar[5]arenes: fascinating cyclophanes with a bright future Chemical Society Reviews, 41 (2). pp. 597-607. ISSN 0306-0012

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Abstract

Pillar[5]arenes are [15]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-dimethoxypillar[5]arene 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 pillar[5]arenes, asymmetric pillar[5]arenes with two different substituents in the 1- and 4-positions and copillar[5]arenes 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 pillar[5]arenes since their recent discovery.

Item Type:Journal article
Additional Information:© Royal Society of Chemistry, 2012
Subjects:C000 Biological and Biomedical Sciences
DOI (a stable link to the resource):10.1039/c1cs15164a
Faculties:Faculty of Science and Engineering > School of Pharmacy and Biomolecular Sciences
ID Code:9475
Deposited By:editor spbs
Deposited On:18 Nov 2011 16:18
Last Modified:10 Oct 2013 15:34

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