Abstract
In 2008, we reported a new class of macrocyclic hosts and named “Pillar[5]arenes”. They combine the advantages and aspects of traditional hosts and have a composition similar to those of typical calix[n]arenes. Pillar[5]arenes have repeating units connected by methylene bridges at the para-position, and thus they have a unique symmetrical pillar architecture differing from the basket-shaped structure of meta-bridged calix[n]arenes. Pillar[5]arenes show high functionality similar to cyclodextrins, and can capture electron accepting guest molecules within their cavity similarly to cucurbit[n]urils. In this review, the synthesis, structure, rotation, host–guest properties, planar chirality and functionality of pillar[5]arenes are discussed, along with pillar[5]arene-based supramolecular architectures and the challenges in synthesizing pillar[6]arenes.
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Acknowledgments
The author thanks the organizing committee of Host–Guest and Supramolecular Chemistry Society, Japan for giving him the HGCS Japan Award of Excellence 2010 and the opportunity of writing this review. He especially acknowledges Prof. Yoshiaki Nakamoto and Prof. Tada-aki Yamagishi (Kanazawa University) for their suggestions and discussions; Mr. Keisuke Kitajima and Mr. Takamichi Aoki (Kanazawa University) for their great contributions to this work. Dr. Shuhei Fujinami (Kanazawa University) for performing X-ray structural analysis. This work was partly supported by Grant-in-Aid for Young Scientists (B) (No. 19750110, 21750140) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
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This article is selected for “HGCS Japan Award of Excellence 2010”.
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Ogoshi, T. Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials. J Incl Phenom Macrocycl Chem 72, 247–262 (2012). https://doi.org/10.1007/s10847-011-0027-2
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DOI: https://doi.org/10.1007/s10847-011-0027-2