A Cyclic Dimer of Metalloporphyrin Forms a Highly Stable Inclusion Complex with C<sub>60</sub>

Tashiro, Kentaro; Aida, Takuzo; Zheng, Jiping; Kinbara, Kazushi; Saigo, Kazuhiko; Sakamoto, Shigeru; Yamaguchi, Kentaro

doi:10.1021/ja992416m

Cited by 325 publications

(200 citation statements)

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“…The unexpectedly close approach of a curved surface to the center of a flat surface was originally recognized in the x-ray crystal structure of a fullerene-porphyrin conjugate (23). Subsequent cocrystallization studies of fullerenes with porphyrins (or metalloporphyrins) established the generality of the phenomenon (24,25), and discrete complexes of fullerenes in bisporphyrin (26) or ''jaws porphyrin'' hosts (27,28) have illustrated the supramolecular chemistry principles involved. The interaction is primarily van der Waals in nature (24) but is influenced by a summation of other weak forces.…”

mentioning

confidence: 96%

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

Sun

Tham

Reed

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

138

121

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Porphyrins and fullerenes are spontaneously attracted to each other. This supramolecular recognition element can be exploited to produce ordered arrays of interleaved porphyrins and fullerenes. C 60⅐H2TpyP⅐Pb(NO3)2⅐1.5TCE (H2TpyP ‫؍‬ tetra-4-pyridylporphyrin; TCE ‫؍‬ 1,1,2,2-tetrachloroethane) crystallizes in the tetragonal P4͞n space group and the structure has been solved to high resolution. The Pb 2؉ ions connect the pyridylporphyrins in infinite sheets with an interlayer spacing of 12.1 Å. The fullerenes are intercalated between these layers, acting as pillars. The 6:6 ring juncture bonds of C 60 are centered over the porphyrins, bringing the layers into strict tetragonal register. This arranagement identifies the fullerene-porphyrin interaction as a structure-defining element. The same motif is seen in a related ribbon structure having C 70 intercalated into HgI 2-linked H2TpyTP. The supramolecular design principles involved in assembling these chromophores may have applications in materials science.

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mentioning

confidence: 96%

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

Sun

Tham

Reed

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

138

121

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“…It suggests a new target for a tri-porphyrin supramolecular host for fullerenes. Cyclic 23 and acyclic ("Jaws") bis-porphyrins 24 are currently used to complex fullerenes in solution. Despite tri-porphyrin complexation of C 60 , the familiar zigzag alternation of fullerenes and porphyrins seen in most tetraarylporphyrin structures can be observed in 4.…”

Section: Resultsmentioning

confidence: 99%

Tapes, Sheets, and Prisms. Identification of the Weak C−F Interactions that Steer Fullerene−Porphyrin Cocrystallization

Hosseini

Hodgson

Tham

et al. 2005

Crystal Growth & Design

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Tetra(pentafluorophenyl)porphyrin (H 2 TPFPP) has been cocrystallized with C 60 from arene solvents to give H 2 TPFPP‚ C 60 , 1, H 2 TPFPP‚C 60 ‚8Benzene, 3, and 3H 2 TPFPP‚2C 60 ‚6Toluene, 4. Their X-ray structures have been determined to identify the supramolecular interactions that lead to tape, sheet, and prismatic packing motifs. In addition to close fullerene-porphyrin π-π interactions, attractive C-F‚‚‚H-C interactions are important in connecting the C 6 F 5 groups of one porphyrin to the pyrrole positions of a neighbor. This interaction is also seen in the structure of the free-base porphyrin H 2 TPFPP‚3p-Xylene, 2.

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“…[48] The inclusion complex 66-67 based on Ru porphyrin dimer 66 [49] and nanocluster 67 composed of two C 60 fullerenes [50] was formed via 66+67 self-assembly in toluene. The host-guest structure is characterized by the association constant of 8.4•10 6 M -1 and was shown to be formed at 66 to 67 ratio < 1.…”

Section: Porphyrin-fullerene Based Molecular Constructsmentioning

confidence: 99%

Synthesis, Properties, and Potential Applications of Porphyrin-Fullerenes

Mironov¹

2011

MHC

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The review focuses current research in the rapidly developing chemistry of porphyrin-fullerene complexes, and highlights recent advances in the synthesis, properties, and potential applications of this family. An overview of the most popular methods to prepare porphyrin complexes with C 60 fullerene exhibiting various types of linkage is given with the main focus on the Prato reaction and its modifications. The discussion of porphyrin-fullerene complexes will include the structures of noncovalently linked porphyrin-fullerenes along with the covalently linked complexes; the chemistry and design of supramolecular ensembles will be covered rather comprehensively. Finally, the potential applications for porphyrin-fullerene conjugates will be discussed.

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A Cyclic Dimer of Metalloporphyrin Forms a Highly Stable Inclusion Complex with C₆₀

Cited by 325 publications

References 1 publication

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

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

Tapes, Sheets, and Prisms. Identification of the Weak C−F Interactions that Steer Fullerene−Porphyrin Cocrystallization

Synthesis, Properties, and Potential Applications of Porphyrin-Fullerenes

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A Cyclic Dimer of Metalloporphyrin Forms a Highly Stable Inclusion Complex with C60

Cited by 325 publications

References 1 publication

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

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

Tapes, Sheets, and Prisms. Identification of the Weak C−F Interactions that Steer Fullerene−Porphyrin Cocrystallization

Synthesis, Properties, and Potential Applications of Porphyrin-Fullerenes

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A Cyclic Dimer of Metalloporphyrin Forms a Highly Stable Inclusion Complex with C₆₀