Neutral Macrocyclic Boxes Spontaneously Assembled from Osmium Tetraoxide, Olefin, and Pyridyl Ligand

Jeong, Kyu Sung; Cho, Young Lag; Song, Jeong Uk; Chang, Hong‐Young; Choi, Moon‐Gun

doi:10.1021/ja982476c

Cited by 63 publications

(11 citation statements)

References 21 publications

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“…Further examples of neutral metallosquares were reported by Alessio and coworkers (square 9) 12 and Jeong et al (square 10). 13 The inertness of Ru-N bond in square 9 allows its purification even by conventional silica-gel chromatography.…”

Section: Concepts For the Preparation Of Molecular Squaresmentioning

confidence: 99%

Metallosupramolecular squares: from structure to function

2004

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Metallosupramolecular squares have been successfully evolved over the past years as versatile substitutes of the conventional organic macrocycles owing to the development of reliable synthetic protocols and abundant structural variability (metals and ligands). In this review we have presented the fundamental aspects of metallosupramolecular squares such as the strategies for their construction (self-assembly vs. kinetically controlled macrocyclization) and characterization. The major emphasis of this tutorial review lies on the function of metallosupramolecular squares. Thus, the introduction of functionality into these systems has been discussed in detail by highlighting the recent progress toward application in various fields, including molecular recognition, enantioselective sensing, photoluminescence, redox activity and electrochemical sensing, and homogeneous catalysis.

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Section: Concepts For the Preparation Of Molecular Squaresmentioning

confidence: 99%

Metallosupramolecular squares: from structure to function

2004

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“…It is therefore an attractive building block for the construction of supramolecular architectures and was frequently used, for example, to control the three‐dimensional folding of molecular strands,12–14 to induce a turn in the polypeptide chain,15 in the construction of rotaxanes,16 catenanes,17 macrocyclic receptors,10, 18–20 self‐assembled macrocyclic boxes,21 and conformationally‐restricted dendrons 22. Crabtree and co‐workers,23, 24 showed that even very simple 2,6‐pyridinediamides bound anions strongly and selectively (although in dichloromethane, a particularly undemanding solvent).…”

Section: Introductionmentioning

confidence: 99%

Anion Recognition by Neutral Macrocyclic Amides

Chmielewski

Jurczak

2005

Chemistry A European J

172

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Although amides often serve as anchoring groups in natural and synthetic anion receptors, the structure-affinity relationship studies of amide-based macrocyclic receptors are still very limited. Therefore, we decided to investigate the influence of the size of the macroring on the strength and selectivity of anion binding by uncharged, amide-based receptors. With this aim, we synthesized a series of macrocyclic tetraamides derived from 2,6-pyridinedicarboxylic acid and aliphatic alpha,omega-diamines of different lengths. X-ray analysis shows that all ligands studied adopt expanded conformations in the solid state with the convergent arrangement of all four hydrogen-bond donors. 1H NMR titrations in DMSO solution revealed a significant effect of the ring size on the stability constants of anion complexes; the 20-membered macrocyclic tetraamide 2 is a better anion receptor than its both 18- and 24-membered analogues. This effect cannot be interpreted exclusively in terms of matching between anion diameter and the size of macrocyclic cavity, because 2 forms the most stable complexes with all anions studied, irrespective of their sizes. However, geometric complementarity manifests in extraordinarily high affinity of 2 towards the chloride anion. The results obtained for solutions were interpreted in the light of solid-state structural studies. Taken together, these data suggest that anion binding by this family of macrocycles is governed by competitive interplay between their ability to adjust to a guest, requiring longer aliphatic spacers, and preorganization, calling for shorter spacers. The 20-membered receptor 2 is a good compromise between these factors and, therefore, it was selected as a promising leading structure for further development of anion receptors. Furthermore, the study of an open chain analogue of 2 revealed a substantial macrocyclic effect. X-ray structure of the acyclic model 14 suggests that this may be due to its ill-preorganized conformation, stabilized by two intramolecular hydrogen bonds.

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“…Similar to the [Ru(bpy) 3 ] 2+ units, the easy synthesis and diversified structural variations of rhenium(I) tricarbonyl diimine units have also been extensively studied as chromophores for anion sensing in the literatures [30,43,57]. [104,105], and rendered them as effective anion receptors through hydrogen bonding. However, in the cases of complexes 26 and 27, there was no chance to form intramolecular hydrogen bonding, but there may be intermolecular hydrogen bonding between the amide protons and the carbonyl groups.…”

Section: Rhenium(i) Complexes For Anion Sensingmentioning

confidence: 99%

Anion recognition and sensing by transition-metal complexes with polarized N H recognition motifs

Chang

Sun

Odago

et al. 2015

Coordination Chemistry Reviews

116

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1. Introduction 2. Ruthenium(II) complexesfor anion sensing 2.1 Pyrrole-based Ru(II) complexes as chemosensors 2.2 Imidazole-based Ru(II) complexes as chemosensors 2.3 Urea-based Ru(II) complexes as chemosensors 2.4 Sulfonamide-based Ru(II) complexes as chemosensors 3. Rhenium(I) complexesfor anion sensing 3.1 Amide-based Re(I) complexes as chemosensors 3.2 Thioamide-and thiourea-based Re(I) complexes as chemosensors 3.3 Sulfonamide-based Re(I) complexes as chemosensors 3.4 Acetylamino-and trifluoroacetylamino-based Re(I) complexes as chemosensors 3.5 Catecholamide-based Re(I) complexes as chemosensors 4. Iridium(III) complexes for anion sensing 4.1 Thiourea-based Ir(III) complexes as chemosensors 4.2 Imidazole-based Ir(III) complexes as chemosensors 5. Concluding remarks Acknowledgements References

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Neutral Macrocyclic Boxes Spontaneously Assembled from Osmium Tetraoxide, Olefin, and Pyridyl Ligand

Cited by 63 publications

References 21 publications

Metallosupramolecular squares: from structure to function

Metallosupramolecular squares: from structure to function

Anion Recognition by Neutral Macrocyclic Amides

Anion recognition and sensing by transition-metal complexes with polarized N H recognition motifs

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