The Synthesis and Solubilization of Amide Macrocycles <i>via</i> Rotaxane Formation

Johnston, Andrew G.; Leigh, David A.; Murphy, Aden; Smart, John P.; Deegan, Michael D.

doi:10.1021/ja962046r

Cited by 141 publications

(80 citation statements)

References 7 publications

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“…Unfortunately, the macrocycle itself could not be used in this study because of its very poor solubility in non-hydrogen bonding solvents. [31] Model compounds 3 (neutral molecule and radical anion) and 4 will be shown to allow separate assignment of the n(CO) bands in the IR spectra to different C=O groups present in the succinamide and naphthalimide moieties of 1, 1C À , 2 and 2C À . Also, B3LYP/6-31G(d) calculations have been performed to predict the nature and frequencies of the vibrational modes and further support the spectral analysis.…”

Section: Introductionmentioning

confidence: 99%

Infrared Study of Intercomponent Interactions in a Switchable Hydrogen‐Bonded Rotaxane

Jagesar

Hartl

Buma

et al. 2008

Chemistry A European J

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The macrocycle in rotaxane 1 is preferentially hydrogen bonded to the succinamide station in the neutral form, but can be moved to the naphthalimide station by one-electron reduction of the latter. The hydrogen bonding between the amide NH groups of the macrocycle and the C double bond O groups in the binding stations in the thread was studied with IR spectroscopy in different solvents in both states. In addition, the solvent effect on the vibrational frequencies was analyzed; a correlation with the solvent acceptor number (AN) was observed. The conformational switching upon reduction could be detected by monitoring the hydrogen-bond-induced shifts of the nu(CO) frequencies of the C double bond O groups of the succinamide and the reduced naphthalimide stations. The macrocycle was found to shield the encapsulated station from the solvent: wavenumbers of nu(CO) bands of the C double bond O groups residing inside the macrocycle cavity remain unaffected by the solvent polarity.

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Section: Introductionmentioning

confidence: 99%

Infrared Study of Intercomponent Interactions in a Switchable Hydrogen‐Bonded Rotaxane

Jagesar

Hartl

Buma

et al. 2008

Chemistry A European J

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“…Simply reacting (figure 9a) the diacid chloride 38 and diamino precursors 39 (in a one-pot prepared using a similar strategy by Leigh and co-workers (Johnston et al 1995(Johnston et al , 1996.…”

Section: Synthetic Approaches To Mechanically Interlocked Moleculesmentioning

confidence: 99%

“…Leigh and co-workers subsequently uncovered a smaller, more compact [2]catenane 42 (Johnston et al 1995), on replacing the diphenylenecyclohexylidene spacer (figure 9b) with a phenylene one, allowing for increased p-p stacking interactions between the two rings. This hydrogen-bonding motif was used in the successful syntheses (figure 9c) of rotaxanes, such as 44, in the presence of the dumbbell 43 (Johnston et al 1996) and, subsequently, a large number of MIMs displaying dynamic features have been prepared (Kay & Leigh 2005) using amide hydrogen bonds as the source of templation. Hydrogen bonding also underpins a mode of templation that involves the threading of secondary dialkylammonium ions (R 2 NH + 2 ) through crown ethers.…”

Section: Synthetic Approaches To Mechanically Interlocked Moleculesmentioning

confidence: 99%

Mechanostereochemistry and the mechanical bond

2012

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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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“…[18] Hydrogen bonding of this type has likewise been employed for clipping syntheses. [19] Furthermore, comparable threading approaches are based on the hydrogen bond driven association of crown ethers and linear secondary ammonium componds [20] or 1,2-bis(pyridinium)-ethanes. [21] The development of host ± guest chemistry started with the discovery of cyclodextrins and crown ethers and was in the beginning mainly focused on the complexation of metal cations.…”

Section: Abstract In Germanmentioning

confidence: 99%

Templates, “Wheeled Reagents”, and a New Route to Rotaxanes by Anion Complexation: The Trapping Method

Seel¹,

Vögtle²

2000

Chem. Eur. J.

111

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The topological aspects of rotaxanes are compared with those of the other families of mechanically interlocked molecules: catenanes and molecular knots. The role of the different types of templates in the well-known threading and clipping procedures often used for rotaxane synthesis are discussed. Finally the conceptually new trapping method that is based on the action of supramolecular nucleophiles formed by anionic stopper-wheel complexes is described.

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The Synthesis and Solubilization of Amide Macrocycles via Rotaxane Formation

Cited by 141 publications

References 7 publications

Infrared Study of Intercomponent Interactions in a Switchable Hydrogen‐Bonded Rotaxane

Infrared Study of Intercomponent Interactions in a Switchable Hydrogen‐Bonded Rotaxane

Mechanostereochemistry and the mechanical bond

Templates, “Wheeled Reagents”, and a New Route to Rotaxanes by Anion Complexation: The Trapping Method

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