Extending supramolecular fullerene-porphyrin chemistry to pillared metal-organic frameworks

Sun, Duixiong; Tham, Fook S.; Reed, Christopher A.; Boyd, Peter D. W.

doi:10.1073/pnas.072602399

Cited by 138 publications

(129 citation statements)

References 39 publications

(44 reference statements)

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“…7 Almost any free-base porphyrin or metalloporphyrin (or like macrocycle) can be cocrystallized with almost any fullerene (or derivatized fullerene) from comixed solutions. [8][9][10][11][12][13] Representative examples are illustrated by H 2 TPP‚ C 60 ‚3toluene (H 2 TPP ) tetraphenylporphyrin) and 2Co-(OEP)‚C 60 ‚CHCl 3 (OEP ) dianion of octaethylporphyrin). As shown in Figures 2 and 3, the structures often adopt an alternating zigzag motif.…”

Section: Fullerene-porphyrin and Fullerene-metalloporphyrin Cocrystalmentioning

confidence: 99%

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Fullerene−Porphyrin Constructs

2004

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Porphyrins and fullerenes are spontaneously attracted to each other. This new supramolecular recognition element can be used to construct discrete host-guest complexes, as well as ordered arrays of interleaved porphyrins and fullerenes. The fullereneporphyrin interaction underlies successful chromatographic separations of fullerenes, and there are promising applications in the areas of porous framework solids and photovoltaic devices.

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Section: Fullerene-porphyrin and Fullerene-metalloporphyrin Cocrystalmentioning

confidence: 99%

“…8 As illustrated in Figure 11, the fullerenes are sandwiched between porphyrinic layers. The interlayer separation has increased to 12.1 Å, accommodating the 10 Å van der Waals diameter of C 60 plus some tetrachloroethane solvate molecules.…”

Section: Fullerene-pillared Metalloporphyrin Frameworkmentioning

confidence: 99%

Fullerene−Porphyrin Constructs

2004

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“…The crystals of [(CoTPP)2‚BPy]‚(C6H5CN)4 (9) and [(ZnTPP)2‚ BPE]‚BPE‚(C6H5CN)3‚C6H5Me (10) were obtained by the evaporation of a toluene/benzonitrile (10:1 v/v) solution (22 mL) containing cobalt(II) tetraphenylporphyrin (CoTPP, 36 mg, 0.054 mmol), BPy (44 mg, 0.27 mmol), and C60 (20 mg, 0.027 mmol) at a 2:10:1 molar ratio (9) or ZnTPP (36 mg, 0.054 mmol), 1,2-bi-(pyridyl)ethylene (BPE, 46 mg, 0.27 mmol), and C60 (20 mg, 0.027 mmol) at a 2:10:1 molar ratio (10). Dark red parallelepipeds of 9 and 10 crystallized without C60 according to the IR spectra and X-ray diffraction data on a single crystal.…”

Section: Methodsmentioning

confidence: 99%

“…Synthesis, crystal structures of 1-4 and 6, and optical properties of 1-7 are described. Crystal structures of three metalloporphyrin dimers of ZnTPP and CoTPP with BPy (8 and 9) and ZnTPP with 1,4-bi-(4,4′-pyridyl)ethylene (10) without fullerenes are also presented, and the geometry of 8 is compared with that of a porphyrin dimer in a complex with C 60 (2).…”

Section: Introductionmentioning

confidence: 99%

“…9 Metal-bridged pyridyl-substituted porphyrins formed another family of fullerene/porphyrin complexes. 10 Another interesting approach is a supramolecular one suggesting that different N-containing ligands, which form porphyrin assemblies in solution can effectively cocrystallize with fullerenes. A large amount of accumulated experience has allowed the preparation of such assemblies in solution and in the solid state without fullerenes.…”

Section: Introductionmentioning

confidence: 99%

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[60]Fullerene Complexes with Supramolecular Zinc Tetraphenylporphyrin Assemblies: Synthesis, Crystal Structures, and Optical Properties

Litvinov

Konarev

Kovalevsky

et al. 2005

Crystal Growth & Design

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Different mono-, bi-, and tetradentate N-and O-containing ligands (L) were used in the design of monomer, dimer, and pentamer zinc tetraphenylporphyrin (ZnTPP) assemblies, which then cocrystallized with fullerene C 60 . Those were pyrazine (1); 4,4′-bipyridyl (2, 8, 9 (with CoTPP)); tetra(4-pyridyl)porphyrin (3); tetrahydrofuran (4); N, N,N′,N′-tetramethyldiaminomethane (5); N,N,N′,N′-tetramethyldiaminoethane (6); N,N,N′,N′-tetramethyldiaminobutene (7); and 1,4-bi-(4,4′-pyridyl)ethylene (10). Molecular structures of new ZnTPP oligomers were described. ZnTPP units, concaved as a result of ligand coordination, effectively cocrystallized with nearly spherical fullerene molecules to produce a variety of packing motifs of fullerenes, namely, three-dimensional (3D) packing in 4, one-dimensional (1D) zigzag chains in 6, a pair arrangement in 1 and 3, and isolated packing in 2. The Zn‚‚‚N(L) bonds were either arranged nearly parallel to the planes of the ligand or bent up to 33°relative to this plane. The characteristic Zn‚‚‚N(L) bond lengths were 2.13-2.21 Å, whereas the Zn‚‚‚C(C 60 ) distances were essentially longer (3.10-3.29 Å). Coordination with ligands and C 60 noticeably shifted the Soret band of ZnTPP to the red side (up to 12 nm) and two Q-bands (up to 26 nm). According to visible-NIR and IR spectra, the complexes had a neutral ground state with charge-transfer bands at 760-820 nm depending on a ZnTPP‚L assembly.

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Porphyrins and Expanded Porphyrins as Receptors

Sessler

Karnas

Sedenberg

2012

Supramolecular Chemistry

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This chapter summarizes recent efforts to use porphyrins and expanded porphyrins as receptors. These unique macrocycles bear resemblance to naturally occurring tetrapyrrolic pigments and have been studied extensively as building blocks for a variety of functional molecular receptors. The introduction discusses the inherent characteristics of porphyrins and their analogs from the perspective of receptor design and is designed to highlight key features. These features include ease of synthesis and functionalization, the hydrogen‐bonding ability of the constituent pyrrolic NH protons, and the fact that the systems in question are often highly colored. This latter feature has afforded an extremely useful means of analyzing host–guest interactions. Because of space limitations, not all of the literature on this topic could be covered in a comprehensive manner. The definition of “receptor” is also limited to species that are thought to be operated via strictly noncovalent‐ or supramolecular‐type interactions. However, this definition is expanded in a few special cases. The goal of this article is not to cite every published article on this topic, but to highlight interesting examples of porphyrin and expanded porphyrins and their utility as receptors. An effort has also been made to describe the analytical techniques used to characterize the resulting host–guest ensembles. This chapter is organized according to the type of guest. One section covers the relatively new area of supramolecular π–π interactions involving porphyrins and nanomaterials, such as fullerenes and nanotubes. Another section discusses porphyrins as receptors for biological entities, including saccharides, peptides, and proteins, as well as DNA. The next section covers porphyrins and expanded porphyrins as anion receptors. This latter treatment includes a discussion of supramolecular electron‐transfer dyads. The use of porphyrins in sensing applications is also presented in summary form. Finally, a perspective on this rapidly growing field of supramolecular chemistry is included in the final remarks. It is hoped that the combination of cited references and listed further readings will allow the interested reader to learn more about this fast‐evolving and fascinating topic.

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Extending supramolecular fullerene-porphyrin chemistry to pillared metal-organic frameworks

Cited by 138 publications

References 39 publications

Fullerene−Porphyrin Constructs

Fullerene−Porphyrin Constructs

[60]Fullerene Complexes with Supramolecular Zinc Tetraphenylporphyrin Assemblies: Synthesis, Crystal Structures, and Optical Properties

Porphyrins and Expanded Porphyrins as Receptors

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