DOSY Study on Dynamic Catenation: Self-Assembly of a [3]Catenane as a Meta-Stable Compound from Twelve Simple Components

Hori, Akiko; Kumazawa, Kazuhisa; Kusukawa, Takahiro; Chand, Dillip Kumar; Fujita, Makoto; Sakamoto, Shigeru; Yamaguchi, Kentaro

doi:10.1002/1521-3765(20011001)7:19<4142::aid-chem4142>3.0.co;2-5

Cited by 96 publications

(37 citation statements)

References 54 publications

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“…Although examples of discrete linear [4]- or [5]catenanes are still rare in the literature, other successful strategies for the synthesis of linear [3]catenanes include an amide-based [3]catenane rotary motor (see section 5.2),[ 102 ] Fujita′s Pd II [3]catenane,[ 103 ] Loeb′s host–guest [3]catenane,[ 104 ] and Sanders’ [3]catenane generated from a DCL. [ 105 ]…”

Section: Higher Order Linear and Radial [N]catenanesmentioning

confidence: 99%

Catenanes: Fifty Years of Molecular Links

2015

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Half a century after Schill and Lüttringhaus carried out the first directed synthesis of a [2]catenane, a plethora of strategies now exist for the construction of molecular Hopf links (singly interlocked rings), the simplest type of catenane. The precision and effectiveness with which suitable templates and/or noncovalent interactions can arrange building blocks has also enabled the synthesis of intricate and often beautiful higher order interlocked systems, including Solomon links, Borromean rings, and a Star of David catenane. This Review outlines the diverse strategies that exist for synthesizing catenanes in the 21st century and examines their emerging applications and the challenges that still exist for the synthesis of more complex topologies.

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Section: Higher Order Linear and Radial [N]catenanesmentioning

confidence: 99%

Catenanes: Fifty Years of Molecular Links

2015

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“…Because of the outwardly complex nature of the composition, we also considered this mixture to be an ideal candidate for analysis by new pure shift NMR methods,[31–33] alongside an array of standard NMR techniques ( 1 H- 1 H COSY, 1 H- 13 C HSQC, 1 H- 13 C HMBC and 1 H DOSY). [34a–f] This is the first time that pure shift diffusion-ordered spectroscopy (DOSY) NMR methodology has been applied to a complex reaction system of partially unknown composition. By using these techniques, we confirmed the direct formation of both TNA nucleoside precursors rac - 15 and rac - 16 (Scheme 2 b) amongst the products from the reaction of 6 and 7 .…”

Section: Introductionmentioning

confidence: 99%

Detection of Potential TNA and RNA Nucleoside Precursors in a Prebiotic Mixture by Pure Shift Diffusion‐Ordered NMR Spectroscopy

Islam¹,

Aguilar²,

Powner³

et al. 2013

Chemistry A European J

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In the context of prebiotic chemistry, one of the characteristics of mixed nitrogenous-oxygenous chemistry is its propensity to give rise to highly complex reaction mixtures. There is therefore an urgent need to develop improved spectroscopic techniques if onerous chromatographic separations are to be avoided. One potential avenue is the combination of pure shift methodology, in which NMR spectra are measured with greatly improved resolution by suppressing multiplet structure, with diffusion-ordered spectroscopy, in which NMR signals from different species are distinguished through their different rates of diffusion. Such a combination has the added advantage of working with intact mixtures, allowing analyses to be carried out without perturbing mixtures in which chemical entities are part of a network of reactions in equilibrium. As part of a systems chemistry approach towards investigating the self-assembly of potentially prebiotic small molecules, we have analysed the complex mixture arising from mixing glycolaldehyde and cyanamide, in a first application of pure shift DOSY NMR to the characterisation of a partially unknown reaction composition. The work presented illustrates the potential of pure shift DOSY to be applied to chemistries that give rise to mixtures of compounds in which the NMR signal resolution is poor. The direct formation of potential RNA and TNA nucleoside precursors, amongst other adducts, was observed. These preliminary observations may have implications for the potentially prebiotic assembly chemistry of pyrimidine threonucleotides, and therefore of TNA, by using recently reported chemistries that yield the activated pyridimidine ribonucleotides.

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“…However, heteroligated hexanuclear assemblies with similar designs to those mentioned above are not known. The known heteroleptic hexanuclear complexes are [(PdL′) 6 (L a )(L b )] 2 ‐type [2]catenanes and [(PdL′) 6 (L a ) 2 (L b ) 4 ]‐type [3]catenanes …”

Section: Self‐assembled Complexes By Using Cis‐protected Palladium(iimentioning

confidence: 99%

Palladium(II)‐Based Self‐Assembled Heteroleptic Coordination Architectures: A Growing Family

Bardhan

Chand

2019

Chemistry A European J

Self Cite

101

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Metal-driven self-assembly is one of the most effective approaches to lucidlydesign alarge range of discrete 2D and 3D coordinationa rchitectures/complexes. Palladium(II)-based self-assembled coordination architectures are usually preparedb yu sing suitable metal components, in either ap artially protected form (PdL')o rt ypical form (Pd; charges are not shown), and designed ligand components. The self-assembled moleculesp repared by using am etal component and only one type of bi-or polydentate ligand (L) can be classified in the homoleptic series of complexes. On the other hand, the less explored heteroleptic series of complexes are obtained by using am etal component and at least two different types of non-chelating bi-or polydentate ligands (such as L a andL b ). Methods that allow the controlled generation of single, discrete heteroleptic complexes are less understood.As urvey of palladium(II)-based self-as-sembled coordination cages that are heteroleptich as been made. This review article illustratesasystematic collection of such architectures and credible justification of their formation, along with reportedf unctional aspects of the complexes.T he collected heteroleptic assemblies are classified here into three sections:1 )[(PdL') m (L a ) x (L b ) y ]-type complexes, in which the denticity of L a and L b is equal; 2) [(PdL') m (L a ) x (L b ) y ]-type complexes, in which the denticity of L a and L b is different;a nd 3) [Pd m (L a ) x (L b ) y ]-type complexes,i n which the denticity of L a and L b is equal. Representative exampleso fs ome important homoleptic architectures are also provided, wherever possible, to set ab ackground for a better understanding of the related heteroleptic versions. The purpose of this review is to pave the way for the construction of severalu nique heteroleptic coordination assemblies that might exhibit emergents upramolecular functions.Review complexes is m + n and the total variety of components is only two. Applications of these homoleptic complexes in various fields, such as catalysis, [3] molecular recognition, [4a-c] sensing [4d] and encapsulationo fv aried guest molecules, [4c, 5] has been widely studied.Elegantarchitectures of biological multi-component systems, for example, metalloproteins and viral capsids,e xploit weak supramolecular interactions in ac ontrolled and harmonious mannerf or their construction by using relevant building blocks. [6] Occurrences of multicomponent systems in biology inspire chemistsw ho seek to advance structurala nd functional complexitieso fs upramolecular systems. Thus, in the field of metallo-supramolecular chemistry, noteworthy efforts have been directed towardt he rational design and controlled synthesis of discrete, heteroleptic structures. The methodsf or the synthesis of discrete, heteroleptic, self-assembled, coordination architectures from various metal components, such as Zn II ,F e II , Hg II ,C r III ,C o III ,R h III ,C u I ,C u II ,R u II and Pt II ,a re well explored by the groups of Lehn,F ujita, Zheng,S tang, Schm...

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DOSY Study on Dynamic Catenation: Self-Assembly of a [3]Catenane as a Meta-Stable Compound from Twelve Simple Components

Cited by 96 publications

References 54 publications

Catenanes: Fifty Years of Molecular Links

Catenanes: Fifty Years of Molecular Links

Detection of Potential TNA and RNA Nucleoside Precursors in a Prebiotic Mixture by Pure Shift Diffusion‐Ordered NMR Spectroscopy

Palladium(II)‐Based Self‐Assembled Heteroleptic Coordination Architectures: A Growing Family

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