science 2005 , 309 , 278-281
DESCRIPTION
Science 2005 , 309 , 278-281. 1996 Nobel Prize. " for their discovery of fullerenes ". Robert F. Curl, Jr., Sir Harold W. Kroto , and Richard E. Smalley. Definition: A class of cage-like carbon compounds composed of fused, pentagonal and/or hexagonal sp 2 carbon rings. - PowerPoint PPT PresentationTRANSCRIPT
![Page 1: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/1.jpg)
Science 2005, 309, 278-281.
![Page 2: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/2.jpg)
" for their discovery of fullerenes"
1996 Nobel Prize
Robert F. Curl, Jr., Sir Harold W. Kroto, and Richard E. Smalley
Definition: A class of cage-like carbon compounds composed of fused, pentagonal and/or hexagonal sp2 carbon rings
![Page 3: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/3.jpg)
Nobel Laureate Richard Smalley Dead At 62
Richard E. Smalley, who was a winner of the 1996 Nobel Pri
ze in Chemistry for the discovery of fullerenes, died on Oct. 28 after a long battle with leukemia. Smalley, 62, was a professor of chemistry and physics at Rice University and founding director of the university’s Center for Nanoscale Science & Technology.Carlos Garcia, one of his colleagues at Rice, says, “We will miss Rick’s brilliance, commitment, energy, enthusiasm, and humanity. He epitomized what we value at Rice: path-breaking research, commitment to teaching, and contribution to the betterment of our world.”Another colleague at Rice, chemistry professor James M. Tour, who says Smalley was “my close friend and my hero,” notes that “a Leonardo da Vinci has passed.”—Ron Dagani
![Page 4: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/4.jpg)
C60
Fullerenes and Their derivatives
C70 C76
C78 C82C84
12 + 20
![Page 5: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/5.jpg)
S.-Y. Xie et al., Science 304, 699 (2004).
Chem. Soc. Perkin Trans. 2, 2001, 487 (2001).
C50Cl10
C36
![Page 6: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/6.jpg)
Phys. Chem. Chem. Phys. 6, 5213 (2004).
nanogram
![Page 7: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/7.jpg)
R. Taylor, Chem. Eur. J. 7, 4074 (2001).
C60
MnF3 , CeF4 ,K2PtF6
F2
![Page 8: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/8.jpg)
Oxyfluorides :CsxPbOyFz [x equals 2, 3, or 4; y from 0.2 to 0.5; and z = (4 + x) – 2y], prepared by partial fluorination (1:9 F2/N2, 500oC, 2 to 4 hours) of appropriate molar ratios of CsCl and PbO2.
fluorinating reagents6.5 g
+ C60
300 mg550 oC, 7h extraction
CCl4/ Hex = 1:1
chromatography
CCl4/ Tol= 1:1
15 mg of fluorinated C58 sprcies
HPLC
1 mg C58F18 (2) C60F18O4 mg C58F17CF3 (1)
![Page 9: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/9.jpg)
-CF3(69 amu)
-CF3-8*F2
-CF3-8*F2-F
EI mass spectrum (70 eV) of C58F17CF3 (1, 1088 amu). (Inset) A spectrum of a second sample.
C60F18O
C58
C58F5CF3
![Page 10: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/10.jpg)
19F NMR spectrum (376MHz) of C58F17CF3 (1).
![Page 11: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/11.jpg)
nine-peak 19F NMR spectrumSee ref 19
![Page 12: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/12.jpg)
C60F17CF3
R. Taylor, J. Chem. Soc. Perkin Trans. 2 2000, 2410 (2000).
![Page 13: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/13.jpg)
![Page 14: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/14.jpg)
Mechanism of formation of perfluoroalkyl derivatives
J. Chem. Soc., Perkin Trans. 2, 2000, 2410–2414
![Page 15: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/15.jpg)
Fig. 5. (Left) Comparison of the chemical shifts for C58F17CF3 (top) and C58F18 (bottom).
![Page 16: Science 2005 , 309 , 278-281](https://reader031.vdocuments.mx/reader031/viewer/2022013103/56813845550346895d9ff0f6/html5/thumbnails/16.jpg)
Conclusion
1. both 1 and 2 appear to be as stable as their C60 counterparts, suggesting that further chemistry of C58 ([58]quasi-fullerene) is in prospect.
2. The HPLC retention times of these C58 compounds are ca. twice those for the corresponding C60 compounds (under conditions detailed above), which may help in identifying further C58 derivatives.