Applications of Pillar[<i>n</i>]arene‐Based Supramolecular Assemblies

Ogoshi, Tomoki; Kakuta, Takahiro; Yamagishi, Toshio

doi:10.1002/anie.201805884

Cited by 221 publications

(88 citation statements)

References 52 publications

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“…In this study, during our investigation of assembly of pillar[n]arenes on a surface, we discovered unexpected self-sorting behaviour dominated by the geometrical complementarity by shape of pillar [n] arenes. Pillar[n]arenes, which were first developed by our group in 2008 12 , have highly symmetrical polygonal tubular structures; examples include pillar [5]arenes and pillar [6]arenes, which are pentagonal and hexagonal molecules, respectively [13][14][15][16][17][18] . Based on strong multivalent ionic interactions, we successfully constructed multilayer films with molecular-scale pores by consecutive adsorption of cationic and anionic pillar [5]arenes onto a solid substrate 19,20 .…”

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Ring shape-dependent self-sorting of pillar[n]arenes assembled on a surface

et al. 2018

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Self-sorting, in which multiple components selectively assemble themselves by recognising self from others, is an attractive approach to produce supramolecular assemblies with controlled structures. Lock-and-key type complementary physical interactions are required for self-sorting because selective affinity is necessary to distinguish self from others. Here we show self-sorting behaviour based on a principle of geometrical complementarity by shape during our investigation of assembly of pentagonal pillar[5]arenes and hexagonal pillar[6] arenes on a surface. In the homoassembly systems, anionic pillar[5]arenes and pillar[6]arenes are adsorbed onto positively charged layers of cationic pillar[5]arenes and pillar[6]arenes, respectively, through cationic-anionic electrostatic interactions. In contrast, ionic pillar[5] arenes are adsorbed onto layers constructed from oppositely charged pillar[5]arenes, but ionic pillar[6]arenes are not. Equally, for the reverse combination, ionic pillar[6]arenes are adsorbed onto layers constructed from oppositely charged pillar[6]arenes, but ionic pillar[5] arenes are not. The geometrical complementarity by shape realises effective self-sorting even in non-directional multivalent ionic interactions.

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Ring shape-dependent self-sorting of pillar[n]arenes assembled on a surface

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“…The designed and prepared macrocyclic hosts [mainly including crown ethers (Liu et al, 2017;Morrison et al, 2017), cyclodextrins Larsen and Beeren, 2019), calixarenes (Wang et al, 2015;Tian et al, 2019), cucurbiturils (Kim et al, 2007;Wu et al, 2018;Xiao B. et al, 2019), and pillar[n]arenes (Xue et al, 2012;Sun et al, 2018;Ogoshi et al, 2019;Xiao T. et al, 2019)] and the investigations of their host-guest properties are the foundation of the development of supramolecular chemistry (Zheng et al, 2012;Yao et al, 2018;Zhang et al, 2019). As the third generation of macrocyclic compounds in supramolecular chemistry, calixarenes process several advantages, such as excellent flexibility, improved conformational mobility, and easy modification (Kim et al, 2012;Nimse and Kim, 2013).…”

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A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water

et al. 2020

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P -tert-butyldihomooxacalix[4]arene is a well-known calix [4]arene analog in which one CH 2 bridge is replaced by one -O-group. Thus, dihomooxacalix[4]arene has a slightly larger cavity than that of calix[4]arene and usually possesses a more flexible cone conformation, and the bridged oxygen atom might provide additional binding sites. Here, we synthesized a new functional p-tert-butyldihomooxacalix[4]arene 1 through Ugi reaction with good yield (70%), starting from condensed p-tert-butyldihomooxacalix [4]arene O-alkoxy-substituted benzaldehydes, benzoic acid, benzylamine, and cyclohexyl isocyanide. Proton nuclear magnetic resonance spectroscopy ( 1 H NMR), 13 C NMR, IR, and diffusion-ordered 1 H NMR spectroscopy (DOSY) methods were used to characterize the structure of 1. Then soft gel was prepared by adding 1 into cyclohexane directly. It shows remarkable thermoreversibility and can be demonstrated for several cycles. As is revealed by scanning electron microscopy (SEM) images, xerogel showed highly interconnected and homogeneous porous network structures, and hence, the gel is suitable for storage and controlled release. . (2019). Enzyme-mediated dynamic combinatorial chemistry allows out-of-equilibrium template-directed synthesis of macrocyclic oligosaccharides. Chem. Sci. 10, 9981-9987.

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“…Pillar[n]arenes (Figure 1a), which were first reported by our group in 2008, are comparatively new macrocyclic compounds in supramolecular chemistry. [9][10][11][12][13][14][15] Thanks to the considerable efforts of pillar[n]arene chemists over the last decade, various advantages of pillar[n]arenes have been revealed, e.g., their easy synthesis from cheap commercially available reagents, 16,17 designable functionalization methods for construction of various supramolecular assemblies and materials, 15,16 selective and strong host-guest interactions in not only organic solvents but also aqueous media, and their highly symmetrical tubular and polygonal structures. 18,19 In particular, the original shape and host-guest properties of pillar[n]arenes are very important aspects for the formation of supramolecular assemblies.…”

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confidence: 99%

One-, Two-, and Three-Dimensional Supramolecular Assemblies Based on Tubular and Regular Polygonal Structures of Pillar[ n ]arenes

Kakuta

Yamagishi

et al. 2019

CCS Chem

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Pillar[ n]arenes, which were first reported by our group in 2008, are promising macrocyclic compounds in supramolecular chemistry. The simple, tubular, and highly symmetrical shape of pillar[ n]arenes has allowed various supramolecular assemblies with well-defined structures to be constructed. The pillar-shaped structures of pillar[ n]arenes are suitable for surface modification and formation of one-dimensional (1D) channels. The regular polygonal prism shape of organized pillar[ n]arenes contributes to the construction of highly assembled structures such as two-dimensional (2D) sheets and three-dimensional (3D) spheres. In this minireview, we describe supramolecular assemblies with various dimensions. First, we discuss 1D supramolecular assemblies based on tubular structures of pillar[ n]arenes. Second, 2D supramolecular sheet formation based on regular polygonal structures is described. Finally, 3D supramolecular assemblies such as vesicles and 3D frameworks constructed from pillar[ n]arenes are discussed.

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Applications of Pillar[n]arene‐Based Supramolecular Assemblies

Cited by 221 publications

References 52 publications

Ring shape-dependent self-sorting of pillar[n]arenes assembled on a surface

Ring shape-dependent self-sorting of pillar[n]arenes assembled on a surface

A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water

One-, Two-, and Three-Dimensional Supramolecular Assemblies Based on Tubular and Regular Polygonal Structures of Pillar[ n ]arenes

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