Monofunctionalized Pillar[5]arene as a Host for Alkanediamines

Strutt, Nathan L.; Forgan, Ross S.; Spruell, Jason M.; Botros, Youssry Y.; Stoddart, J. Fraser

doi:10.1021/ja111418j

Cited by 487 publications

(299 citation statements)

References 73 publications

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“…[6] NMR spectroscopy binding studies with pillar [5]arene 2 in CDCl 3 provided log K a values of 1.50(6) for 16a and 1.45(7) for 16b; these values are in good agreement with the data reported for related systems. [6] The treatment of 16a and 16b with 3,5-dinitrobenzoyl chloride (17) in the presence of pillar [5]arene 2 in CHCl 3 at -15°C gave [2]rotaxanes 19a and 19b. [2]Rotaxanes 20a and 20b were obtained under similar conditions from 3,5-bis(trifluoromethyl)benzoyl chloride (18).…”

Section: Resultssupporting

confidence: 83%

“…[2] Simple alkyl-substituted guests are efficiently encapsulated in the cavities of pillar [5]arenes to generate pseudorotaxanes. [5,6] Such host-guest complexes are perfectly suited for the synthesis of [2]rotaxanes. [7] Stoddart and co-workers were the first to report the synthesis of a [a] yields must be related to the different affinities for the various monoacylated intermediates.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Pillar[5]arene‐Based [2]Rotaxanes from Acyl Chlorides and Amines

et al. 2014

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Pillar [5]arene-based [2]rotaxanes have been prepared from the reactions of diacyl chloride reagents with various amine stoppers. The yields of the [2]rotaxanes are sensitive to the reaction conditions (solvent and stoichiometry) as well as to structural and electronic factors. In particular, the nature of the starting amine reagent has a dramatic influence on the yields of [2]rotaxanes; thus, the reaction outcome is not simply related to the binding constant of the diacyl chloride reagent with the pillar[5]arene. Indeed, the differences in the

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Section: Resultssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Preparation of Pillar[5]arene‐Based [2]Rotaxanes from Acyl Chlorides and Amines

et al. 2014

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“…3 (2013)guest complexes with neutral alkylamines and 1. 46 The K value of 1,8-diaminooctane with 1 (Run 1) was much larger than that observed for n-octylamine (Run 2). The complexation between the other neutral guests and peralkylated pillar [5]arenes was studied by Jia and Li et al 68,69 The K value of 1,4-dibromobutane with 2 (Run 11) was also much larger than that observed for bromobutane (Run 17).…”

Section: Hostguest Propertiesmentioning

confidence: 71%

New Synthetic Host Pillararenes: Their Synthesis and Application to Supramolecular Materials

Ogoshi

Yamagishi

2013

Bulletin of the Chemical Society of Japan

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In 2008, we reported a new class of macrocyclic hosts called "pillararenes." They combine the advantages and aspects of traditional hosts and have a composition similar to those of typical calixarenes. Pillararenes have repeating units connected by methylene bridges at the para-position of benzene moieties, and thus they have a unique symmetric pillar architecture differing from the basket-shaped structure of calixarenes bridged at the meta-position of benzene moieties. Pillararenes show high functionality similar to cyclodextrins and can capture electron-accepting guest molecules within their cavity similarly to cucurbiturils. In this account, the synthesis, structure, and hostguest properties are discussed, along with pillararene-based supramolecular architectures.

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“…Cucurbiturils, cyclic oligomers of glycoluril units with binding properties similar to those of the cyclodextrins, have been exploited, particularly by Kim and co-workers, in the assembly of spectacular molecular necklaces and polyrotaxanes (Kim 2002). Calixarenes, cyclic oligomers of phenols linked by meta-methylene groups (Arduini et al 2003(Arduini et al , 2009, are also prevalent in the literature, while the recently discovered pillar [5]arenes, their para-linked siblings, have subsequently been incorporated into MIMs (Strutt et al 2011).…”

Section: Synthetic Approaches To Mechanically Interlocked Moleculesmentioning

confidence: 99%

Mechanostereochemistry and the mechanical bond

2012

Self Cite

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The chemistry of mechanically interlocked molecules (MIMs), in which two or more covalently linked components are held together by mechanical bonds, has led to the coining of the term mechanostereochemistry to describe a new field of chemistry that embraces many aspects of MIMs, including their syntheses, properties, topologies where relevant and functions where operative. During the rapid development and emergence of the field, the synthesis of MIMs has witnessed the forsaking of the early and grossly inefficient statistical approaches for template-directed protocols, aided and abetted by molecular recognition processes and the tenets of self-assembly. The resounding success of these synthetic protocols, based on templation, has facilitated the design and construction of artificial molecular switches and machines, resulting more and more in the creation of integrated functional systems. This review highlights (i) the range of template-directed synthetic methods being used currently in the preparation of MIMs; (ii) the syntheses of topologically complex knots and links in the form of stable molecular compounds; and (iii) the incorporation of bistable MIMs into many different device settings associated with surfaces, nanoparticles and solid-state materials in response to the needs of particular applications that are perceived to be fair game for mechanostereochemistry.

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Monofunctionalized Pillar[5]arene as a Host for Alkanediamines

Cited by 487 publications

References 73 publications

Preparation of Pillar[5]arene‐Based [2]Rotaxanes from Acyl Chlorides and Amines

Preparation of Pillar[5]arene‐Based [2]Rotaxanes from Acyl Chlorides and Amines

New Synthetic Host Pillararenes: Their Synthesis and Application to Supramolecular Materials

Mechanostereochemistry and the mechanical bond

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