Fullerene oxides and ozonides

Heymann, D.; Weisman, R. Bruce

doi:10.1016/j.crci.2006.02.003

Cited by 47 publications

(25 citation statements)

References 103 publications

(243 reference statements)

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“…Oxygen may thus form a long list of oxides with C 60 , including hetero C 59 O, possibly O@C 60 , and many somewhat unstable exohedral mono-or poly-oxides (see e.g. Heymann & Weisman 2006). Christian et al (1992a) have reported that C 59 O + significantly forms in collisions of O + with C 60 and is amazingly stable for collision energies up to at least ∼30 eV.…”

Section: Oxygen Compoundsmentioning

confidence: 99%

See 1 more Smart Citation

Interstellar fullerene compounds and diffuse interstellar bands

Omont

2016

A&A

100

103

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Recently, the presence of fullerenes in the interstellar medium (ISM) has been confirmed and new findings suggest that these fullerenes may possibly form from polycyclic aromatic hydrocarbons (PAHs) in the ISM. Moreover, the first confirmed identification of two strong diffuse interstellar bands (DIBs) with the fullerene, C + 60 , connects the long standing suggestion that various fullerenes could be DIB carriers. These new discoveries justify reassessing the overall importance of interstellar fullerene compounds, including fullerenes of various sizes with endohedral or exohedral inclusions and heterofullerenes (EEHFs). The phenomenology of fullerene compounds is complex. In addition to fullerene formation in grain shattering, fullerene formation from fully dehydrogenated PAHs in diffuse interstellar clouds could perhaps transform a significant percentage of the tail of low-mass PAH distribution into fullerenes including EEHFs. But many uncertain processes make it extremely difficult to assess their expected abundance, composition and size distribution, except for the substantial abundance measured for C + 60 . EEHFs share many properties with pure fullerenes, such as C 60 , as regards stability, formation/destruction and chemical processes, as well as many basic spectral features. Because DIBs are ubiquitous in all lines of sight in the ISM, we address several questions about the interstellar importance of various EEHFs, especially as possible carriers of diffuse interstellar bands. Specifically, we discuss basic interstellar properties and the likely contributions of fullerenes of various sizes and their charged counterparts such as C + 60 , and then in turn: 1) metallofullerenes; 2) heterofullerenes; 3) fulleranes; 4) fullerene-PAH compounds; 5) H 2 @C 60 . From this reassessment of the literature and from combining it with known DIB line identifications, we conclude that the general landscape of interstellar fullerene compounds is probably much richer than heretofore realized. EEHFs, together with pure fullerenes of various sizes, have many properties necessary to be suitably carriers of DIBs: carbonaceous nature; stability and resilience in the harsh conditions of the ISM; existing with various heteroatoms and ionization states; relatively easy formation; few stable isomers; spectral lines in the right spectral range; various and complex energy internal conversion; rich Jahn-Teller fine structure. This is supported by the first identification of a DIB carrier as C + 60 . Unfortunately, the lack of any precise information about the complex optical spectra of EEHFs and most pure fullerenes other than C 60 and about their interstellar abundances still precludes definitive assessment of the importance of fullerene compounds as DIB carriers. Their compounds could significantly contribute to DIBs, but it still seems difficult that they are the only important DIB carriers. Regardless, DIBs appear as the most promising way of tracing the interstellar abundances of various fullerene compounds if the breakthr...

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Section: Oxygen Compoundsmentioning

confidence: 99%

“…The most stable exohedral oxide is the epoxy C 60 O with a bridging bond of O on one double bond C=C of C 60 (Heymann & Weisman 2006); however, it is very unstable (Christian et al 1992a). It should therefore be rapidly photolyzed by the interstellar UV radiation.…”

Section: Oxygen Compoundsmentioning

confidence: 99%

Interstellar fullerene compounds and diffuse interstellar bands

Omont

2016

A&A

100

103

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“…It gives a wide range of stable oxidation products comprising epoxy, keto, and ester moieties, as well as peroxy moieties. Two reviews in this field should be noted 15,281 . Although various conditions of O 3 reaction with fullerenes and fullerenecontaining composites were used 280, 282 -291 , the majority of studies consider fullerene ozonides as the primary molecular intermediates of ozonolysis, whose subsequent reactions give the observed range of products and cause CL 283,288 .…”

Section: Reaction Of Fullerenes With Ozonementioning

confidence: 99%

Peroxide intermediates of oxidation processes: Organic trioxides

Khursan

2014

Patai's Chemistry of Functional Groups

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The review discusses the results of studies on the chemistry of organic trioxides ROOOR (R = H or an organic radical) carried out in the past years. The spectral identification, structure, thermal stability and chemical properties of HOOOH, HOOO ⋅ , hydrotrioxides, open‐chain and cyclic trioxides (including fullerene ozonides) are described. The significance of trioxides for biochemistry, environmental chemistry, and organic synthesis is much higher than it was believed previously. The chemical reactions that these compounds undergo resemble those of peroxides. However, the temperature range in which trioxide reactions occur is shifted considerably towards low temperatures. Homolytic decomposition at one of the OO bonds is the most typical reaction of trioxides. Trioxides are liable to induced and catalytic decomposition. Hydrotrioxides demonstrate high oxidative activity. Decomposition of some trioxides is accompanied by efficient generation of singlet oxygen.

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“…The infrared spectra of such derivatives show a series of surprising analogies with the spectra of ozonized fullerenes (3)(4)(5)(6). The subject of fullerene oxides derived from the ozonation of C 60 and C 70 fullerenes has been reviewed a few times (6)(7)(8)(9). In general the early stages of reaction with ozone with C 60 and C 70 involve the formation of molozonides which decompose into epoxide groups, leading to fullerene polyoxides (10).…”

Section: Introductionmentioning

confidence: 96%

Thermal Decomposition of Ozonized C₇₀Fullerene and Its Reducing Properties Toward Silver Ions

Cataldo

Hafez

Iglesias‐Groth

2015

Fullerenes, Nanotubes and Carbon Nanostructures

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Ozonized C 70 fullerene known as C 70 ozopolymer or C 70 fullerene polyoxide was thermally decomposed in a DSC (Differential Scanning Calorimeter). The exothermal decomposition enthalpy was measured together with the activation energy for the thermal decomposition. The decomposition of C 70 ozopolymer was also studied with FT-IR spectroscopy showing that the thermal treatment at 350°C under N 2 causes the disappearance of the secondary ozonide groups and a series of the rearrangements of the oxygenated groups present in the compound. The Downloaded by [New York University] at 22:08 17 June 2015 ACCEPTED MANUSCRIPT ACCEPTED MANUSCRIPT 2 reduction properties of C 70 ozopolymer were successfully assessed in the formation of silver nanoparticles from an acqueous solution of Ag + ions.

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Fullerene oxides and ozonides

Cited by 47 publications

References 103 publications

Interstellar fullerene compounds and diffuse interstellar bands

Interstellar fullerene compounds and diffuse interstellar bands

Peroxide intermediates of oxidation processes: Organic trioxides

Thermal Decomposition of Ozonized C₇₀Fullerene and Its Reducing Properties Toward Silver Ions

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Fullerene oxides and ozonides

Cited by 47 publications

References 103 publications

Interstellar fullerene compounds and diffuse interstellar bands

Interstellar fullerene compounds and diffuse interstellar bands

Peroxide intermediates of oxidation processes: Organic trioxides

Thermal Decomposition of Ozonized C70Fullerene and Its Reducing Properties Toward Silver Ions

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Thermal Decomposition of Ozonized C₇₀Fullerene and Its Reducing Properties Toward Silver Ions