Coordination-Driven Self-Assembly of Metallodendrimers Possessing Well-Defined and Controllable Cavities as Cores

Yang, Hai Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J.

doi:10.1021/ja066804h

Cited by 130 publications

(77 citation statements)

References 66 publications

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“…2l,5a,11c,12 As shown in Scheme 4a, a non-functional scaffold ( 9 ) can be obtained from starting assembly 3 by the addition of 1,3-dicarboxylate ligand 8 and Pt(II) acceptor 1 . The 5-position of the phenyl ring of 8 can be further functionalized by standard synthesis and then used to modify 3 .…”

Section: Resultsmentioning

confidence: 99%

Designed Post-Self-Assembly Structural and Functional Modifications of a Truncated Tetrahedron

et al. 2011

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Post-self-assembly modifications of a discrete metal-organic supramolecular structure have been developed. Such modifications allow the properties of the self-assembled supramolecular species to be changed in a simple and efficient manner (>90% yield). Initiated by the application of chemical stimuli, the post-self-assembly modifications described herein result in three distinct changes to the supramolecular system: an individual building-block component change, an overall structural modification, and a functional evolution of a [6 + 4] metal-organic supramolecular structure. The three modifications have been carefully examined by a range of characterization methods including NMR and UV-Vis spectroscopy, electrospray ionization mass spectrometry (ESI-MS), pulsed field gradient spin echo (PGSE) NMR measurements, electrochemical analysis, and computational simulations.

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Section: Resultsmentioning

confidence: 99%

Designed Post-Self-Assembly Structural and Functional Modifications of a Truncated Tetrahedron

et al. 2011

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“…In this way, numerous functional moieties including porphyrin,7 diaza-crown ether,8 cavitand,9 carborane,10 and chiral metallocorners 7b,11 have been introduced into the supramolecular architectures. Furthermore, covalently grafting a functional moiety on the exterior surface of an angle-directed building block has resulted in a large number of discrete supramolecular metal-organic assemblies peripherally functionalized with dendrimers, 12 ferrocene,3d,13 crown ethers, and pseudorotaxanes 14. Lastly, the interior surface of self-assembled suprastructures can also be decorated via covalent attachment of a functional moiety on the concave side of a directional building block.…”

Section: Introductionmentioning

confidence: 99%

Construction of Endo-Functionalized Two Dimensional Metallacycles via Coordination-Driven Self-Assembly

et al. 2009

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The synthesis of three endofunctionalized two-dimensional supramolecular metallacycles including two [2 + 2] rhomboids (5 and 6) and a [3 + 3] hexagon (7) is reported. The resulting self-assembled supramolecular structures, containing several nitrobenzyl moieties at their interior surface, have been fully characterized by multinuclear NMR ( 31 P and 1 H) and electrospray ionization mass spectrometry. A significant C-H…O hydrogen bonding between the nitrobenzyl acceptor and the edge molecules of the supramolecular architecture is observed in the small rhomboid 5 and this interaction gradually decreases upon the enlargement of the resulting polygonal structures from a small rhomboid 5 through a large rhomboid 6 to a hexagon 7. Molecular modeling with the MMFF force field gives a possible conformation of each self-assembly in different solvents and shows that the hydrophilic nitrobenzyl moiety prefers to be buried in the cavity of the resulting polygonal structures in nonpolar solvents, thus forming hydrogen bonds with the peripheral component building units.

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“…These difficulties produce complex synthetic routes, low yields, or restrictions in the structures that can be formed. Methods to overcome this ring/chain equilibrium include pre‐organization and dynamic supramolecular assembly 6, 7, 8…”

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Ferrocene‐ and Biferrocene‐Containing Macrocycles towards Single‐Molecule Electronics

et al. 2017

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Cyclic multiredox centered systems are currently of great interest, with new compounds being reported and developments made in understanding their behavior. Efficient, elegant, and high‐yielding (for macrocyclic species) synthetic routes to two novel alkynyl‐conjugated multiple ferrocene‐ and biferrocene‐containing cyclic compounds are presented. The electronic interactions between the individual ferrocene units have been investigated through electrochemistry, spectroelectrochemistry, density functional theory (DFT), and crystallography to understand the effect of cyclization on the electronic properties and structure.

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Coordination-Driven Self-Assembly of Metallodendrimers Possessing Well-Defined and Controllable Cavities as Cores

Cited by 130 publications

References 66 publications

Designed Post-Self-Assembly Structural and Functional Modifications of a Truncated Tetrahedron

Designed Post-Self-Assembly Structural and Functional Modifications of a Truncated Tetrahedron

Construction of Endo-Functionalized Two Dimensional Metallacycles via Coordination-Driven Self-Assembly

Ferrocene‐ and Biferrocene‐Containing Macrocycles towards Single‐Molecule Electronics

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