Host size effect in the complexation of two bis(m-phenylene)-32-crown-10-based cryptands with a diazapyrenium salt

Zhang, Xichang; Zhai, Chunxi; Li, Ning; Liu, Ming; Li, Shijun; Zhu, Kelong; Zhang, Jinqiang; Huang, Feihe; Gibson, Harry W.

doi:10.1016/j.tetlet.2007.08.038

Cited by 19 publications

(5 citation statements)

References 40 publications

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“…For this purpose, crown ether-based cryptands have been explored . After the first dibenzo-30-crown-10 (DB30C10)-based cryptand was reported by Stoddart and co-workers in 1985, Gibson, Huang, and co-workers designed and prepared a series of cryptands based on bis( m -phenylene)-32-crown-10 (BMP32C10) (Figure , 39 ), − which was a type of bicyclic crown ethers containing two 1,3,5-phenylene units linked by three bridges. They not only offer much better binding affinities than the corresponding simple crown ethers, but also can be used to form pseudorotaxanes and rotaxanes with various small organic guests such as paraquat, bisparaquat, diquat, diazapyrenium, monopyridinium, bispyridium, trispyridinium, and imidazolium salts (Figure ). − …”

Section: Synthesis Of Rotaxanes Based On Various Macrocyclesmentioning

confidence: 99%

Development of Pseudorotaxanes and Rotaxanes: From Synthesis to Stimuli-Responsive Motions to Applications

et al. 2015

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Introduction 7399 2. Synthesis of Rotaxanes Based on Various Macrocycles 7400 2.1. Crown Ethers 7401 2.1.1. Bis(m-phenylene)-32-crown-10 and Crown Ethers with Larger Sizes 7401 2.1.2. Dibenzo-24-crown-8 7402 2.1.3. Benzo-21-crown-7 7406 2.1.4. Crown Ether-Based Cryptands 7407 2.2. Cyclodextrins 7410 2.3. Cucurbiturils 7413 2.3.1. Cucurbit[6]uril 7413 2.3.2. Cucurbit[7]uril 7414 2.3.3. Cucurbit[8]uril 7415 2.4. Calixarenes 7416 2.4.1. Calix[4]arenes as Linkers or Stoppers 7416 2.4.2. Calix[5]arenes and Calix[6]arenes as Wheels 7416 2.4.3. Heterocalix[n]arenes or Calix[n]heteroarenes 7417 2.5. Pillararenes 7418 2.5.1.

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Section: Synthesis Of Rotaxanes Based On Various Macrocyclesmentioning

confidence: 99%

Development of Pseudorotaxanes and Rotaxanes: From Synthesis to Stimuli-Responsive Motions to Applications

et al. 2015

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“…In cryptand complexes, we mainly focused on paraquat-based systems not only because they are widely used precursors for the construction of rotaxanes, catenanes, and even metal–organic frameworks but also because their interesting redox properties make them good building blocks for molecular machines, nanocontainers, and molecular devices. Cryptands are also wonderful hosts for other organic guests such as diquat ( 7 ), ,, diazapyrenium ( 12 ), monopyridinium ( 13 ), bispyridinium ( 14 ), trispyridinium ( 15 ), bisimidazolium ( 16 ), bisparaquat ( 17 ), 1,2-bis(pyridinium)ethane ( 18 ), vinylogous viologen ( 19 ), and tropylium salts ( 20 ) . Due to the preorganization and additional or optimized binding sites, the cryptand complexes all display better stabilities than the corresponding simple crown ether-based analogues.…”

Section: Pseudorotaxanesmentioning

confidence: 99%

Stimuli-Responsive Host–Guest Systems Based on the Recognition of Cryptands by Organic Guests

et al. 2014

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CONSPECTUS: As the star compounds in host-guest chemistry, the syntheses of crown ethers proclaimed the birth of supramolecular chemistry. Crown ether-based host-guest systems have attracted great attention in self-assembly processes because of their good selectivity, high efficiency, and convenient responsiveness, enabling their facile application to the "bottom-up" approach for construction of functional molecular aggregates, such as artificial molecular machines, drug delivery materials, and supramolecular polymers. Cryptands, as preorganized derivatives of crown ethers, not only possess the above-mentioned properties but also have three-dimensional spatial structures and higher association constants compared with crown ethers. More importantly, the introduction of the additional arms makes cryptand-based host-guest systems responsive to more stimuli, which is crucial for the construction of adaptive or smart materials. In the past decade, we designed and synthesized crown ether-based cryptands as a new type of host for small organic guests with the purpose of greatly increasing the stabilities of the host-guest complexes and preparing mechanically interlocked structures and large supramolecular systems more efficiently while retaining or increasing their stimuli-responsiveness. Organic molecules such as paraquat derivatives and secondary ammonium salts have been widely used in the fabrication of functional supramolecular aggregates. Many host molecules including crown ethers, cyclodextrins, calixarenes, cucurbiturils, pillararenes, and cryptands have been used in the preparation of self-assembled structures with these guest molecules, but among them cryptands exhibit the best stabilities with paraquat derivatives in organic solvents due to their preorganization and additional and optimized binding sites. They enable the construction of sophisticated molecules or supramolecules in high yields, affording a very efficient way to fabricate stimuli-responsive functional supramolecular systems. This Account mainly focuses on the application of cryptands in the construction of mechanically interlocked molecules such as rotaxanes and catenanes, and stimuli-responsive host-guest systems such as molecular switches and supramolecular polymers due to their good host-guest properties. These cryptands are bicyclic derivatives of crown ethers, including dibenzo-24-crown-8, bis(m-phenylene)-26-crown-8, dibenzo-30-crown-10, and bis(m-phenylene)-32-crown-10. The length of the third arm has a very important influence on the binding strength of these cryptands with organic guests, because it affects not only the size fit between the host and the guest but also the distances and angles that govern the strengths of the noncovalent interactions between the host and the guest. For example, for bis(m-phenylene)-32-crown-10-based cryptands, a third arm of nine atoms is the best. The environmental responsiveness of these cryptand-based host-guest systems arises from either the crown ether units or the third arms. For example, a dibenzo...

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“…2a-c,3 It has been proved that bis(m-phenylene)-32-crown-10-based cryptands, compared with the corresponding simple bis(mphenylene)-32-crown-10 (BMP32C10), are powerful hosts to complex paraquat derivatives (N,N -dialkyl-4,4 -bipyridinium salts), 4 diquat, 5 monopyridinium salts, 6 and diazapyrenium salts. 7 The much stronger complexation between cryptands and guests should result in higher efficiency, when these cryptands instead of BMP32C10 are used to prepare mechanically interlocked structures with these guests. Herein, we report for the first time the syntheses of bis(m-phenylene)-32-crown-10-based cryptand/paraquat derivative [2]rotaxanes.…”

Section: Introductionmentioning

confidence: 99%

High-yield preparation of [2]rotaxanes based on the bis(m-phenylene)-32-crown-10-based cryptand/paraquat derivative recognition motif

Liu

Zhang

et al. 2008

Org. Biomol. Chem.

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Host size effect in the complexation of two bis(m-phenylene)-32-crown-10-based cryptands with a diazapyrenium salt

Cited by 19 publications

References 40 publications

Development of Pseudorotaxanes and Rotaxanes: From Synthesis to Stimuli-Responsive Motions to Applications

Development of Pseudorotaxanes and Rotaxanes: From Synthesis to Stimuli-Responsive Motions to Applications

Stimuli-Responsive Host–Guest Systems Based on the Recognition of Cryptands by Organic Guests

High-yield preparation of [2]rotaxanes based on the bis(m-phenylene)-32-crown-10-based cryptand/paraquat derivative recognition motif

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