Four constitutional isomers of BMpillar[5]arene: synthesis, crystal structures and complexation with n-octyltrimethyl ammonium hexafluorophosphate

Zhang, Zibin; Luo, Yan; Xia, Binyuan; Han, Chengyou; Yu, Yihua; Chen, Xiaopeng; Huang, Feihe

doi:10.1039/c0cc03732j

Cited by 146 publications

(54 citation statements)

References 22 publications

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“…7b) [70], in which the 1 H NMR signals of the benzene, methylene bridge and alkoxy moieties were split. After that, nonsymmetric pentabutylated-penta-methylated pillar [5]arene (28) was also reported by Huang and Meier groups [71,72]. Hunag and coworkers reported copillar [5]arenes.…”

Section: Pillar[5]arene and Pillar[6]arene Derivativesmentioning

confidence: 68%

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

Ogoshi

2011

J Incl Phenom Macrocycl Chem

173

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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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Section: Pillar[5]arene and Pillar[6]arene Derivativesmentioning

confidence: 68%

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

Ogoshi

2011

J Incl Phenom Macrocycl Chem

173

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“…(c) Slipped-stacked structure formed by per-hydroxylated pillar [5]arene 12 [5] crystallized from its acetone solution. 131 and nonsymmetric amphiphilic pillar [5]arene 113a [5] crystallized from a mixture of dichloromethane and methanol 134 assembled into one-dimensional channels. Examples of slipped-stacked structures constructed from the assembly of pillar [5]arene molecules were per-pentylated pillar [5]arene 5 [5] crystallized from acetone, 54 per-isobutylated pillar [5]arene 9 [5] crystallized from a mixture of dichloromethane and acetonitrile, 135 pillar [5]arenes with two benzoquinones (22 [5] and 24 [5]) from a mixture of dichloromethane and acetonitrile, 148 and pillar [5]arene with 10 ethylene oxide 50 [5] ⊃paraquat complex from a mixture of isopropyl ether and acetonitrile.…”

Section: Assembled Structure Of Pillar[n]arenesmentioning

confidence: 99%

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

2016

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In 2008, we reported a new class of pillar-shaped macrocyclic hosts, known as "pillar[n]arenes". Today, pillar[n]arenes are recognized as key players in supramolecular chemistry because of their facile synthesis, unique pillar shape, versatile functionality, interesting host-guest properties, and original supramolecular assembly characteristics, which have resulted in numerous electrochemical and biomedical material applications. In this Review, we have provided historical background to macrocyclic chemistry, followed by a detailed discussion of the fundamental properties of pillar[n]arenes, including their synthesis, structure, and host-guest properties. Furthermore, we have discussed the applications of pillar[n]arenes to materials science, as well as their applications in supramolecular chemistry, in terms of their fundamental properties. Finally, we have described the future perspectives of pillar[n]arene chemistry. We hope that this Review will provide a useful reference for researchers working in the field and inspire discoveries concerning pillar[n]arene chemistry.

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“…The obtained product was a mixture of four constitutional isomers. Four constitutional isomers of another nonsymmetric pillar[5]arene (R A1–E1 = CH 3 , R A2–E2 = n ‐C 4 H 9 ) were successfully isolated and completely characterized by X‐ray crystal analysis by Huang et al16a and by Meier and Cao et al16b…”

Section: Versatile Functionality Of Pillararenesmentioning

confidence: 99%

Pillararenes: Versatile Synthetic Receptors for Supramolecular Chemistry

2013

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In 2008 we reported a new class of macrocyclic hosts that we named “pillararenes”. To date, pillar[5]arenes and pillar[6]arenes, containing five and six repeating units, respectively, have been synthesized. Pillar[5]arenes and pillar[6]arenes can accommodate 10 and 12 substituent groups, respectively. The position‐selective versatile functionalization of these substituents enables the preparation of various supramolecular assemblies. Here we discuss the synthesis and selective functionalization of pillararenes. We also discuss the use of the various pillararene derivatives as components of supramolecular assemblies such as sensors, a self‐inclusion complex, supramolecular dimers, polymers, an alternating polymer consisting of pillar[5]arene and pillar[6]arene units, systems in which pillararene shuttles along an axle, rotaxanes, polyrotaxanes, and pillar[5]arene‐based bulk‐materials, as well as colloidal assembly of pillararenes, biomedical applications, and hybridization with inorganic materials.

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Four constitutional isomers of BMpillar[5]arene: synthesis, crystal structures and complexation with n-octyltrimethyl ammonium hexafluorophosphate

Abstract: Four constitutional isomers of BMpillar[5]arene were prepared from 1-butoxy-4-methoxybenzene and they showed different binding abilities with n-octyltrimethyl ammonium hexafluorophosphate.

Cited by 146 publications

References 22 publications

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

Pillararenes: Versatile Synthetic Receptors for Supramolecular Chemistry

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