Planar-Chiral Pillar[5]arene: Chiral Switches Induced by Multiexternal Stimulus of Temperature, Solvents, and Addition of Achiral Guest Molecule

Ogoshi, Tomoki; Shiga, Ryohei; Yamagishi, Toshio; Nakamoto, Yoshiaki

doi:10.1021/jo1021508

Cited by 115 publications

(74 citation statements)

References 27 publications

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“…We synthesized pillar [5]arene with 10 2(S)-methylbutoxy groups 8 [5] (Figure 21). 55 The diastereomeric excess (de%) of 8 [5] was changed by solvent, temperature, and inclusion of a guest molecule. The dynamic planar chirality change will be applied in chiral molecular recognition and as catalysts ( Figure 16).…”

Section: Conformational and Planar Chirality Characteristics Of Pillamentioning

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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Section: Conformational and Planar Chirality Characteristics Of Pillamentioning

confidence: 99%

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

2016

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“…20 All the normal pillararenes are racemic mixtures with two equivalent conformations (pS and pR). It is interesting and important to investigate pillararenes' planar chirality and its controllable factors.…”

Section: Catenanesmentioning

confidence: 99%

Efficient complexation between pillar[5]arenes and neutral guests: from host–guest chemistry to functional materials

2016

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Since their discovery in 2008, pillar[n]arenes have been a popular family of macrocyclic arene hosts due to their accessible one-step synthesis, convenient functionalization, symmetrical prism structures and perfect cavity host-guest properties. Compared with other macrocyclic hosts, the most peculiar recognition behavior of pillararenes is the strong binding affinities of pillar[5]arenes (P5As) towards neutral guests in organic media, which is unfeasible for classic crown ethers and calixarenes. The intriguing properties have found extensive applications in many fields from supramolecular chemistry to materials science. This feature article provides a detailed summary of the molecular recognition of P5As and neutral guests, where the driving forces, binding mechanisms, and binding selectivities are comprehensively discussed. Furthermore, brief highlights of research progress in the functional applications based on the neutral guest⊂P5A motifs were also discussed, including the construction of complex topological superstructures (e.g. rotaxanes, catenanes and daisy chains), supramolecular polymers, and functional materials.

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“…7a) [67]. The branched alkyl-substituted pillar [5]arene (25) [68] and pillar [5]arene containing chiral 2-(S)-methylbutoxy moieties at both rims (26) [69] were also synthesized. Using 1-ethoxy-4-methoxybenzene as a monomer, we synthesized nonsymmetric penta-ethylated-penta-methylated pillar [5]arene (27, Fig.…”

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

confidence: 99%

“…Compound 26 exhibited planar chirality and interconversion between (pS)-26 and (pR)-26 occurred. The diastereomeric excess of 26 was relatively small, so the introduction of bulky chiral substituents and/or many asymmetric carbon moieties at the rims enhances diastereomeric excess [69].…”

Section: Peralkylated Pillar[5]arenesmentioning

confidence: 99%

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

Ogoshi

2011

J Incl Phenom Macrocycl Chem

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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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Planar-Chiral Pillar[5]arene: Chiral Switches Induced by Multiexternal Stimulus of Temperature, Solvents, and Addition of Achiral Guest Molecule

Cited by 115 publications

References 27 publications

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

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

Efficient complexation between pillar[5]arenes and neutral guests: from host–guest chemistry to functional materials

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

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