Toward Self-Assembled Surface-Mounted Prismatic Altitudinal Rotors. A Test Case:  Trigonal and Tetragonal Prisms

Caskey, Douglas C.; Michl, Josef

doi:10.1021/jo050409c

Cited by 39 publications

(24 citation statements)

References 29 publications

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“…42,43 Numerous chemical and biological systems 23,24,44,45,46,47,48 have been studied with this method, including our nanoscopic dodecahedra. 20 The present results are summarized in Table 1.…”

Section: Diffusion Constant Determinationmentioning

confidence: 99%

Coordination-Driven Face-Directed Self-Assembly of Trigonal Prisms. Face-Based Conformational Chirality

et al. 2008

Self Cite

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The coordination-driven self-assembly of four different trigonal prisms from three equivalents of one of four different tetrapyridyl star connectors and six equivalents of a platinum linker dication in nitromethane is presented. This face-directed approach affords high yield without template assistance. The prisms have been characterized by multinuclear and DOSY NMR and dual ESI-FT-ICR mass spectrometry. The use of a conformationally chiral star connector leads to a conformationally chiral prism when connector arm ends attached to a vertex have a strongly correlated twist sense and chirality is communicated across polyhedral faces, edges and vertices. Molecular mechanics results suggest that in the smallest prism 3d collective effects dominate and the all-P and all-M conformers are strongly favored. NMR data prove that the two edges of the pyridine rings in the triflate salts of 3a -3d are distinct. An Eyring plot of rates obtained from lineshape analysis and 1-D EXCHSY NMR yields an activation enthalpy ΔH ‡ of ∼12 kcal/mol and activation entropy ΔS ‡ of ∼-15 cal/mol.K for the edge interconversion process, compatible with pyridine rotation around the Pt-N bond. For 3c, this behavior is observed only up to ∼318 K. At higher temperatures, the Eyring plot is again linear but follows a very different straight line, with ΔH ‡ of ∼35 kcal/mol and ΔS ‡ of ∼60 cal/mol.K. This highly unusual result is further investigated and discussed in the following companion paper.

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Section: Diffusion Constant Determinationmentioning

confidence: 99%

Coordination-Driven Face-Directed Self-Assembly of Trigonal Prisms. Face-Based Conformational Chirality

et al. 2008

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“…Once adjusted, the quantitative formation of tetragonal prisms via [4+2] assembly can take place [59].…”

Section: Prismatic Metallacagesmentioning

confidence: 99%

Coordination-Driven Supramolecular Macromolecules via the Directional Bonding Approach

Cook

Stang

2013

Hierarchical Macromolecular Structures: 60 Years After the Staudinger Nobel Prize I

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Coordination-driven self-assembly is a process that generates supramolecular architectures from molecular precursors by exploiting the favorable properties of metal-ligand bonding. The discrete supramolecular coordination complexes (SCCs) thus obtained have enjoyed multiple decades of development, focused initially on the design and reactivity of rigid building blocks with specific directionalities and angularities, thereby populating a molecular library of complementary donor and acceptor subunits. More recently, efforts have broadened to encompass pre-and post-self-assembly modifications, which have lead to new routes for obtaining functionalized metallacages and metallacycles, multicomponent assemblies incorporating multiple types of ligands in a single scaffold, and supramolecular transformations that quantitatively alter the structure of a given SCC, furnishing an entirely new architecture.

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“…Michl et al proposed prismatic 3D networks consisting of linear rods and starshaped connectors linked by Pt(II) metals at the corners (Scheme 20) [106]. For example, treatment of biphenyl rods and 1,3,5-tris(4-pyridylethynyl)phenyl caps gave trigonal prism complex 57a [107]. MM calculation suggested that its framework was slightly twisted from the regular trigonal prism to form a chiral structure.…”

Section: Cage Network With Coordination Linkersmentioning

confidence: 99%

Three-Dimensional Aromatic Networks

Toyota

Iwanaga

2012

Topics in Current Chemistry

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Three-dimensional (3D) networks consisting of aromatic units and linkers are reviewed from various aspects. To understand principles for the construction of such compounds, we generalize the roles of building units, the synthetic approaches, and the classification of networks. As fundamental compounds, cyclophanes with large aromatic units and aromatic macrocycles with linear acetylene linkers are highlighted in terms of transannular interactions between aromatic units, conformational preference, and resolution of chiral derivatives. Polycyclic cage compounds are constructed from building units by linkages via covalent bonds, metal-coordination bonds, or hydrogen bonds. Large cage networks often include a wide range of guest species in their cavity to afford novel inclusion compounds. Topological isomers consisting of two or more macrocycles are formed by cyclization of preorganized species. Some complicated topological networks are constructed by self-assembly of simple building units.

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Toward Self-Assembled Surface-Mounted Prismatic Altitudinal Rotors. A Test Case: Trigonal and Tetragonal Prisms

Cited by 39 publications

References 29 publications

Coordination-Driven Face-Directed Self-Assembly of Trigonal Prisms. Face-Based Conformational Chirality

Coordination-Driven Face-Directed Self-Assembly of Trigonal Prisms. Face-Based Conformational Chirality

Coordination-Driven Supramolecular Macromolecules via the Directional Bonding Approach

Three-Dimensional Aromatic Networks

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