Novel Open-Cage Fullerenes Having a 12-Membered-Ring Orifice:  Removal of the Organic Addends from the Rim of the Orifice

Vougioukalakis, Georgios C.; Prassides, Kosmas; Orfanopoulos, Michael

doi:10.1021/ol049843b

Cited by 40 publications

(119 citation statements)

References 15 publications

Supporting

Mentioning

116

Contrasting

Unclassified

Order By: Relevance

“…However, recently, the research group of Orfanopoulos claimed the structure of 17 on the basis of 1 H coupled and selective decoupled 13 C NMR studies. 49,50 Their conclusion about the cleavage position differs from ours as shown in Scheme 13. However, assignment of the fullerene carbon was not given clearly.…”

Section: Expansion Of the Orifice Of The Open-cage Ketolactam C 60mentioning

confidence: 58%

Open-Cage Fullerenes: Synthesis, Structure, and Molecular Encapsulation

Iwamatsu¹,

Murata²

2005

Synlett

View full text Add to dashboard Cite

The carbon-carbon bond scission of the fullerene cage offers an open-cage fullerene derivative having an opening on the fullerene surface. This account summarizes our recent studies on the syntheses of open-cage C 60 derivatives as well as their properties of molecular encapsulation. The photochemical rearrangement of the cyclohexadiene derivative of C 60 gives bis(fulleroid), the precursor for the cage scission. The photooxygenative carbon-carbon bond cleavage of bis(fulleroid) affords an open-cage diketone derivative having a 12-membered ring. The reaction of the diketone derivative with aromatic hydrazine or hydrazone allows the ring expansion of the orifice by regioselective cage scission to yield a product bearing a 16-membered ring. The orifice in the product is large enough to pass a hydrogen molecule, producing an endohedral hydrogen complex. In the case of the reaction with ortho-phenylenediamine, two carbon-carbon bonds are sequentially cleaved to afford a product having a 20-membered ring orifice. This product spontaneously encapsulates one water molecule to form an endohedral water complex. Hydrogen (H 2 ) 4.2 Water 5Conclusion and Future Aspects

show abstract

Section: Expansion Of the Orifice Of The Open-cage Ketolactam C 60mentioning

confidence: 58%

Open-Cage Fullerenes: Synthesis, Structure, and Molecular Encapsulation

Iwamatsu¹,

Murata²

2005

Synlett

View full text Add to dashboard Cite

show abstract

“…However, the number of new lines is considerably less than would be expected if the cage opened. 15 In contrast, the change in the cubane lines is striking. The original lines disappear completely, only a weak IR line at 2948 cm −1 indicates that there are still hydrocarbon groups in the sample.…”

Section: Poly(cmentioning

confidence: 95%

Vibrational Spectra of C₆₀·C₈H₈ and C₇₀·C₈H₈ in the Rotor-stator and Polymer Phases

et al. 2007

View full text Add to dashboard Cite

C60·C8H8 and C70·C8H8 are prototypes of rotor-stator cocrystals. We present infrared and Raman spectra of these materials and show how the rotor-stator nature is reflected in their vibrational properties. We measured the vibrational spectra of the polymer phases poly(C60C8H8) and poly(C70C8H8) resulting from a solid state reaction occurring on heating. Based on the spectra we propose a connection pattern for the fullerene in poly(C60C8H8), where the symmetry of the C60 molecule is D 2h . On illuminating the C60·C8H8 cocrystal with green or blue light a photochemical reaction was observed leading to a similar product to that of the thermal polymerization.

show abstract

“…The method is also applicable to Wudl's open-cage compound ketolactam 25, yielding 42, as reported by Orfanopoulos and coworkers. [51] Compound 31 was isolated as a minor product in the reaction of 5 with singlet oxygen.…”

Section: Hole-enlargement Reactionsmentioning

confidence: 99%

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Gan¹,

Yang²,

Zhang³

et al. 2010

Advanced Materials

View full text Add to dashboard Cite

Open-cage fullerenes can act as hosts for small molecules such as water, nitrogen, or hydrogen, forming endohedral fullerenes. Following a brief summary of carbon, nitrogen, and oxygen insertion in the fullerene framework to form homofullerenes, methods of creating a hole in the fullerene surface are surveyed. Techniques of hole enlargement and the insertion of atoms or molecules through the orifice to form endohedral fullerenes are described. Finally, the possibility of subsequent closure of the hole is considered.

show abstract

Novel Open-Cage Fullerenes Having a 12-Membered-Ring Orifice: Removal of the Organic Addends from the Rim of the Orifice

Abstract: Two novel open-cage fullerene derivatives bearing a 12-membered-ring orifice on the fullerene cage have been isolated. Removal of the N-MEM protective group leads to the first open-cage [60]fullerene derivative without organic addends on the rim of the orifice. [structure: see text]

Cited by 40 publications

References 15 publications

Open-Cage Fullerenes: Synthesis, Structure, and Molecular Encapsulation

Open-Cage Fullerenes: Synthesis, Structure, and Molecular Encapsulation

Vibrational Spectra of C₆₀·C₈H₈ and C₇₀·C₈H₈ in the Rotor-stator and Polymer Phases

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Contact Info

Product

Resources

About

Novel Open-Cage Fullerenes Having a 12-Membered-Ring Orifice: Removal of the Organic Addends from the Rim of the Orifice

Abstract: Two novel open-cage fullerene derivatives bearing a 12-membered-ring orifice on the fullerene cage have been isolated. Removal of the N-MEM protective group leads to the first open-cage [60]fullerene derivative without organic addends on the rim of the orifice. [structure: see text]

Cited by 40 publications

References 15 publications

Open-Cage Fullerenes: Synthesis, Structure, and Molecular Encapsulation

Open-Cage Fullerenes: Synthesis, Structure, and Molecular Encapsulation

Vibrational Spectra of C60·C8H8 and C70·C8H8 in the Rotor-stator and Polymer Phases

Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices

Contact Info

Product

Resources

About

Vibrational Spectra of C₆₀·C₈H₈ and C₇₀·C₈H₈ in the Rotor-stator and Polymer Phases