Stoichiometric Self-Assembly of Isomeric, Shape-Persistent, Supramacromolecular Bowtie and Butterfly Structures

Schultz, Anthony; Li, Xiaopeng; Barkakaty, Balaka; Moorefield, Charles N.; Wesdemiotis, Chrys; Newkome, George R.

doi:10.1021/ja303177v

Cited by 107 publications

(70 citation statements)

References 41 publications

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“…[13,14] Coordination-driven self-assembly using tailored 2,2':6',2''-terpyridine (tpy) building blocks has highlighted their ability to form stable linear tpy À M II À tpy complexes as the structural walls of the polygons possessing rigid organic vertices. [25][26][27] Recently, we have reported various heteroleptic materials, such as a hexagonal spoked wheel, [28] molecular bowties and butterflies, [29] and a molecular rhombus, [30] which were obtained by either multicomponent or one-step assembly. [24] Both homoleptic and heteroleptic connectivity has been used extensively in these assemblies, but heteroleptic assembly with a need for multicomponent building blocks still remains challenging owing to a tendency to produce competitive products.…”

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confidence: 99%

One‐Step Multicomponent Self‐Assembly of a First‐Generation Sierpiński Triangle: From Fractal Design to Chemical Reality

et al. 2014

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A novel terpyridine-based architecture that mimics a first-generation Sierpiński triangle has been synthesized by multicomponent assembly and features tpy-Cd(II)-tpy connectivity (tpy=terpyridine). The key terpyridine ligands were synthesized by the Suzuki cross-coupling reaction. Mixing two different terpyridine-based ligands and Cd(II) in a precise stoichiometric ratio (1:1:3) produced the desired fractal architecture in near-quantitative yield. Characterization was accomplished by NMR spectroscopy, mass spectrometry, and transmission electron microscopy.

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One‐Step Multicomponent Self‐Assembly of a First‐Generation Sierpiński Triangle: From Fractal Design to Chemical Reality

et al. 2014

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“…With these new terpyridines added to our molecular quiver, two polycyclic, macromolecular, constitutional isomers (Schultz et al, 2012a) were constructed ( Figure 21). As in the case of synthesizing large ring structures, use of the dimeric terpyridine 48 restricted the degrees-of-freedom of reaction and subsequently facilitated optimum conditions for isolation of either molecular bowtie 49 when reacted with tetrakisterpyridine 47 or the isomeric molecular butterfly motif 50 when treated with tetrakisterpyridine 46.…”

Section: Molecular Fractal Design and Uti-litymentioning

confidence: 99%

From dendrimers to fractal polymers and beyond

Moorefield

Schultz²,

Newkome

2013

Braz. J. Pharm. Sci.

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The advent of dendritic chemistry has facilitated materials research by allowing precise control of functional component placement in macromolecular architecture. The iterative synthetic protocols used for dendrimer construction were developed based on the desire to craft highly branched, high molecular weight, molecules with exact mass and tailored functionality. Arborols, inspired by trees and precursors of the utilitarian macromolecules known as dendrimers today, were the first examples to employ predesigned, 1 → 3 C-branched, building blocks; physical characteristics of the arborols, including their globular shapes, excellent solubilities, and demonstrated aggregation, combined to reveal the inherent supramolecular potential (e.g., the unimolecular micelle) of these unique species. The architecture that is a characteristic of dendritic materials also exhibits fractal qualities based on self-similar, repetitive, branched frameworks. Thus, the fractal design and supramolecular aspects of these constructs are suggestive of a larger field of fractal materials that incorporates repeating geometries and are derived by complementary building block recognition and assembly. Use of terpyridine-M2+-terpyridine (where, M = Ru, Zn, Fe, etc) connectivity in concert with mathematical algorithms, such as forms the basis for the Seirpinski gasket, has allowed the beginning exploration of fractal materials construction. The propensity of the fractal molecules to self-assemble into higher order architectures adds another dimension to this new arena of materials and composite construction.

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“…-tpy[ (tpy = [2,2 0 :6 0 ,2 00 ]terpyridine and M = Ru, Fe, Zn or Cd) connectivity to fabricate supramacromolecules has distinct advantages due to the diversity of metal coordination, unique metal-ligand physical properties, rigidity, and ability to incorporate predesigned, structured directionality. Recently, this building protocol has led to the creation of several 2D-and 3D-nano-structures, including bowtie-, butterfly-, and spoke wheel-shaped supramolecules [16][17][18][19]. As well, the porphyrin analogues of [n]cycloparaphenylenes are known [7d].…”

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confidence: 99%