Relatively high-yield syntheses of rotaxanes. Syntheses and properties of compounds consisting of cyclodextrins threaded by .alpha.,.omega.-diaminoalkanes coordinated to cobalt(III) complexes

Ogino, Hiroshi

doi:10.1021/ja00395a091

Cited by 276 publications

(106 citation statements)

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“…[44][45][46][47][48] Ogino reported the first rotaxane using cyclodextrin (CD) as the ring molecule. 49 CDs are cyclic oligosaccharides comprising six, seven, or eight glucose units with inner diameters of 0.44, 0.58, or 0.74 nm, respectively, that are called -, -, or -CDs in that order. 41,50,51 As compared to other cyclic molecules, CDs are readily available in both high purities and large quantities and can be modified with various functional groups.…”

mentioning

confidence: 99%

Novel Cross-Linking Concept of Polymer Network: Synthesis, Structure, and Properties of Slide-Ring Gels with Freely Movable Junctions

Ito

2007

Polym J

353

298

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ABSTRACT:We have recently developed a novel type of gel called the slide-ring gel or topological gel that is different from physical and chemical gels by using the supramolecular architecture with topological characteristics. In this gel, polymer chains with bulky end groups exhibit neither covalently cross-links as in chemical gels nor attractive interactions as in physical gels but are topologically interlocked by figure-of-eight cross-links. Hence, these crosslinks can pass along the polymer chains freely to equalize the tension of the threading polymer chains similarly to pulleys; this is called the pulley effect. The slide-ring gel is a new cross-linking concept for the polymer network as well as a real example of a slip-link model or sliding gel, which was previously considered only theoretically. In this study, we review the synthesis, structure, and mechanical properties of the slide-ring gels with freely movable cross-linking junctions based primarily on our recent studies. The pulley effect of the slide-ring gels has been recently confirmed by mechanical measurements, small-angle neutron scattering (SANS), small-angle X-ray scattering (SAXS), quasi-elastic light scattering (QELS), etc. This concept can be applied to not only gels but also to a wide variety of polymeric materials without solvents.

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confidence: 99%

Novel Cross-Linking Concept of Polymer Network: Synthesis, Structure, and Properties of Slide-Ring Gels with Freely Movable Junctions

Ito

2007

Polym J

353

298

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“…Significant attention has recently been given to coordination chemistry, which has found applications in the construction of complicated or nano-sized structures, catenanes, 1,2 rotaxanes, [3][4][5] helices, 6,7 molecular squares, [8][9][10] tetrahedral hosts, [11][12][13][14][15][16] and so on. [17][18][19][20][21] Coordination compounds exist not only as discrete molecules in solution, but also as compounds with infinite periodicity in the crystal state.…”

mentioning

confidence: 99%

Solvent-dependent Assembly of Discrete and Continuous CoCl2 Adamantane-based Ligand Complexes: Observations by CSI–Mass Spectrometry and X-ray Crystallography

et al. 2013

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773Significant attention has recently been given to coordination chemistry, which has found applications in the construction of complicated or nano-sized structures, catenanes, 1,2 rotaxanes, [3][4][5] helices, 6,7 molecular squares, 8-10 tetrahedral hosts, [11][12][13][14][15][16] and so on. 17-21Coordination compounds exist not only as discrete molecules in solution, but also as compounds with infinite periodicity in the crystal state. Coordination polymers (CPs) and metal-organic frameworks (MOFs) are well-known crystals constructed by an organic compound and a metal. Porous CPs (PCPs) and MOFs, in particular, are highly potential materials for gas storage, 22-24 ion exchange, 25-28 heterogeneous catalysis, 29-31 separation, 29,[32][33][34][35][36] and non-linear optics, 37-39 because of the nanospace separated from bulk space.Structure construction with a coordination bond plays a critical role in the formation of a complicated structure and the introduction of functionality into the structure for basic research and industrial applications. In structure control, it is important to adjust the metal-ligand stoichiometry based on the number of coordination sites or the coordination environment. For example, Lehn and coworkers 40 demonstrated the spontaneous formation of a cylindrical complex from five ligands and six metal ions, in which two hexaazatriphenylene derivatives acting as the planar molecule and three bisbipyridyl ligands linked at the 5,5′ positions acting as the pillar molecule were connected by three copper ions. The structure was characterized by 1 H NMR spectroscopy, fast atom bombardment mass spectrometry (MS), and single-crystal X-ray structure analysis. The concept of adjusting metal-ligand stoichiometry has been widely accepted in discrete complexes and CPs, depending on the metal coordination geometry and the ligand binding site. However, complex preparation relies on many factors, such as the temperature, concentration, and the counter ion. For instance, Fujita and coworkers 41 demonstrated the treatment of Pd(NO3)2 and a ditopic bidentate ligand assembled into a mixture of M4L8 and M3L6 box-like structures, depending on the ratio of dimethylsulfoxide to acetonitrile.In such an environment-dependent complex formation, advanced functions, including molecular switching and molecular catch and release, for instance, have been obtained in recent years. However, structure elucidation of obtained complexes is generally difficult by using only 1 H NMR analysis in the case that the numbers of ligands and metals are not known. Therefore, limited studies of environment-dependent complexes have been reported up to the present. [42][43][44][45][46] Conventional MS using electron ionization, chemical ionization, fast atom bombardment, and electro-spray ionization cannot detect large coordination complexes because the weak coordination bonds dissociate during ionization. Cold-spray ionization MS (CSI-MS) is one of the most promising solutions to this problem, 47 as it can detect coordination complexes w...

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“…Most syntheses of MIMs containing cyclodextrins follow a host-guest strategy whereby a guest is encircled by the cyclodextrin (the host) to form a pseudorotaxane, and the ends of the guest are either joined together to form a catenane, or capped with stoppers to form a rotaxane. This threading-followedby-stoppering approach yielded (figure 7a) the first cyclodextrin rotaxane 27 in 1981, when Ogino threaded 1,12-diaminododecane 26 through both a-and b-cyclodextrin and stoppered the pseudorotaxanes formed in each case by coordination of a Co(III) 25 to the terminal amino functions of the guest (Ogino 1981). The key to the success of this approach lies in the fact that all components are soluble in water, which also enhances the recognition of the thread by the cyclodextrin torus, and that the capping reaction is tolerant to aqueous conditions.…”

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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Relatively high-yield syntheses of rotaxanes. Syntheses and properties of compounds consisting of cyclodextrins threaded by .alpha.,.omega.-diaminoalkanes coordinated to cobalt(III) complexes

Cited by 276 publications

References 0 publications

Novel Cross-Linking Concept of Polymer Network: Synthesis, Structure, and Properties of Slide-Ring Gels with Freely Movable Junctions

Novel Cross-Linking Concept of Polymer Network: Synthesis, Structure, and Properties of Slide-Ring Gels with Freely Movable Junctions

Solvent-dependent Assembly of Discrete and Continuous CoCl2 Adamantane-based Ligand Complexes: Observations by CSI–Mass Spectrometry and X-ray Crystallography

Mechanostereochemistry and the mechanical bond

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