Synthesis of pillar[7]arene

Chen, Yu; Hong, Tao; Kou, Yu; Meier, Herbert; Fu, Jian Long; Cao, De Rong

doi:10.1016/j.cclet.2012.03.026

Cited by 42 publications

(13 citation statements)

References 11 publications

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“…www.chemeurj.org action, or the interaction of C À H bonds with p systems on account of increased polarization by the halogen substituent. [7,10,15,33] The host-guest interactions not only provide the construction strategy but also stabilize the obtained assemblies. In addition, the solvent effects play an important role in fabricating both host-guest complexes and the assemblies.…”

Section: Driving Force and Theory For Pillararene-based Assembliesmentioning

confidence: 99%

“…Pillararenes integrate the advantages of other existing host molecules, for example, similar cavity size to cyclodextrins, similar chemical composition to calixarenes, and similar molecular recognition ability to cucurbiturils. Furthermore, pillararenes possess their own unique characteristics, such as relatively easy preparation and functionalization procedures, [10][11][12][13][14][15][16][17][18] owning highly symmetric structure, which recognizes special guests without further modifications. Up to now, the synthesis, [10][11][12][13][14][15][16][17][18] modifications, [19][20][21][22][23][24][25] and molecular recognition [26,27] of pillararenes have been explored extensively.…”

Section: Introductionmentioning

confidence: 99%

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Pillararene‐Based Assemblies: Design Principle, Preparation and Applications

Zhang

Zhao

2013

Chemistry A European J

211

114

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In this review, we highlight recent advancements on pillararene-based assemblies. The driving forces for the formation of the pillararene-based assemblies are discussed first. The host-guest interactions are deemed as not only general strategy for constructing assemblies but also essential components for preventing the assemblies from the dissociation. Solvent effect is also important in the assembling process, since it could influence the host-guest interactions and provide solvophobic effect on pillararenes for the assembly. Then, several pillararene-based assembly architectures are introduced, including pillararene-based interlocked structures, such as (poly)pseudorotaxanes, (poly)rotaxanes, and daisy chains, classified by their topological structures and synthetic strategy. The morphologies of the supramolecular assemblies are divided into several types, for example, nanospheres, nanotubes and supramolecular polymers. Furthermore, the functions and potential applications are summarized accompanied with related assembly structures. The review not only provides fundamental findings, but also foresights future research directions in the research area of pillararene-based assemblies.

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Section: Driving Force and Theory For Pillararene-based Assembliesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pillararene‐Based Assemblies: Design Principle, Preparation and Applications

Zhang

Zhao

2013

Chemistry A European J

211

114

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“…In 2011 a moderate‐yield (yield 35–45 %) synthesis of pillar[6]arenes was reported by the same group 5. Syntheses of pillar[ n ]arenes ( n = 7–10) were recently reported by Cao et al6 and Hou et al,7 but these reactions suffered from low yields (1–2 %).…”

Section: Introductionmentioning

confidence: 98%

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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“…The reaction of 1,4-dimethoxybenzene with paraformaldehyde in the presence of BF 3 ·OEt 2 to form 1,4-dimethoxypillar[5]arene (DMpillar[5]arene), followed by the removal of the methoxyl protecting groups with BBr 3 constitutes the first ever synthesis (Scheme ) of pillar[5]arene. Numerous investigations − have been carried out to optimize this Friedel–Crafts alkylation to form good yields of pillar[5]arene , or pillar[6]arene, coupled with moderate to low yields of pillar[7–14]arenes. − …”

Section: Introductionmentioning

confidence: 99%

Functionalizing Pillar[n]arenes

et al. 2014

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Macrocyclic chemistry has relied on the dominance of some key cavitands, including cyclodextrins, calixarenes, cyclophanes, and cucurbiturils, to advance the field of host-guest science. Very few of the many other cavitands introduced by chemists during these past few decades have been developed to near the extent of these four key players. A relatively new family of macrocycles that are becoming increasingly dominant in the field of macrocyclic chemistry are the pillar[n]arenes composed of n hydroquinone rings connected in their 2- and 5-positions by methylene bridges. This substitution pattern creates a cylindrical or pillar-like structure that has identical upper and lower rims. The preparation of pillar[n]arenes is facile, with pillar[5]- through pillar[7]arene being readily accessible and the larger macrocycles (n = 8-14) being accessible in diminishing yields. The rigid pillar[n]arene cavities are highly π-electron-rich on account of the n activated aromatic faces pointing toward their centers, allowing the cavities to interact strongly with a range of π-electron-deficient guests including pyridiniums, alkylammoniums, and imidazoliums. The substitution pattern of pillar[n]arenes bestows chirality onto the macrocycle in the form of n chiral planes. The absolute configuration of the chiral planes in pillar[n]arenes can be either fixed or rapidly undergoing inversion. The future of pillar[n]arenes is going to be dependent on their ability to fulfill specific applications. Chemical modification of the parent pillar[n]arenes lets us create functionalized hosts with anticipated chemical or physical properties. The featured potential applications of pillar[n]arenes to date are far reaching and include novel hosts with relevance to nanotechnology, materials science, and medicine. Pillar[n]arenes have an overwhelming advantage over other hosts since the number of ways available to incorporate handles into their structures are diverse and easy to implement. In this Account, we describe the routes to chemically modified pillar[n]arenes by discussing the chemistry of their functionalization: monofunctionalization, difunctionalization, rim differentiation, perfunctionalization, and phenylene substitution. We assess the synthetic complications of employing these functionalization procedures and survey the potential applications and novel properties that arise with these functionalized pillar[n]arenes. We also highlight the challenges and the synthetic approaches that have yet to be fully explored for the selective chemical modification of these hosts. Finally, we examine a related class of macrocycles and consider their future applications. We trust that this Account will stimulate the development of new methods for functionalizing these novel hosts to realize pillar[n]arene-containing compounds capable of finding applications.

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Synthesis of pillar[7]arene

Cited by 42 publications

References 11 publications

Pillararene‐Based Assemblies: Design Principle, Preparation and Applications

Pillararene‐Based Assemblies: Design Principle, Preparation and Applications

Pillararenes: Versatile Synthetic Receptors for Supramolecular Chemistry

Functionalizing Pillar[n]arenes

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