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

Cragg, Peter J., Sharma, Kushal·2012·Chem. Soc. Rev.
DOI 10.1039/c1cs15164a
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Abstract

Pillar[5]arenes are [1(5)]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 D(5) 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.

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Metadata

Authors
Cragg, P. J., & Sharma, K.
Venue
Chem. Soc. Rev.
Publisher
Royal Society of Chemistry (RSC)
Published
2012
Volume
41
Issue
2
Pages
597-607
ISSN
  • 0306-0012 (ISSN-L)
  • 1460-4744
DOI
10.1039/c1cs15164a
OpenAlex
W2168042943
Cited by
531
References
0
FWCI
1.23
Type
journal article
Language
en
Open access
closed

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Cragg, P. J., & Sharma, K. (2012). Pillar[5]arenes: fascinating cyclophanes with a bright future. Chem. Soc. Rev. https://doi.org/10.1039/c1cs15164a

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