Science 2005, 309, 278-281.

" 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

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

C60

Fullerenes and Their derivatives

C70 C76

C78 C82C84

12 + 20

S.-Y. Xie et al., Science 304, 699 (2004).

Chem. Soc. Perkin Trans. 2, 2001, 487 (2001).

C50Cl10

C36

Phys. Chem. Chem. Phys. 6, 5213 (2004).

nanogram

R. Taylor, Chem. Eur. J. 7, 4074 (2001).

C60

MnF3 , CeF4 ,K2PtF6

F2

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)

-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

19F NMR spectrum (376MHz) of C58F17CF3 (1).

nine-peak 19F NMR spectrumSee ref 19

C60F17CF3

R. Taylor, J. Chem. Soc. Perkin Trans. 2 2000, 2410 (2000).

Mechanism of formation of perfluoroalkyl derivatives

J. Chem. Soc., Perkin Trans. 2, 2000, 2410–2414

Fig. 5. (Left) Comparison of the chemical shifts for C58F17CF3 (top) and C58F18 (bottom).

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.