1. Science 2005, 309, 278-281.

2. " 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 sp 2 carbon rings

3. Nobel Laureate Richard Smalley Dead At 62 Richard E. Smalley, who was a winner of the 1996 Nobel Prize 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

4. C 60 Fullerenes and Their derivatives C 70 C 76 C 78 C 82 C 84

5. S.-Y. Xie et al., Science 304, 699 (2004). Chem. Soc. Perkin Trans. 2, 2001, 487 (2001). C 50 Cl 10 C 36

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

7. R. Taylor, Chem. Eur. J. 7, 4074 (2001). C 60 MnF 3, CeF 4,K 2 PtF 6 F2F2

8. 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 F 2 /N 2, 500 o C, 2 to 4 hours) of appropriate molar ratios of CsCl and PbO 2. fluorinating reagents 6.5 g + C 60 300 mg 550 o C, 7hextraction CCl 4 / Hex = 1:1 chromatography CCl 4 / Tol= 1:1 15 mg of fluorinated C 58 sprcies HPLC 1 mg C 58 F 18 (2) C 60 F 18 O 4 mg C 58 F 17 CF 3 (1)

9. -CF 3 (69 amu) -CF 3 -8*F 2 -CF 3 -8*F 2 -F EI mass spectrum (70 eV) of C 58 F 17 CF 3 (1, 1088 amu). (Inset) A spectrum of a second sample. C 60 F 18 O C 58 C 58 F 5 CF 3

10. 19 F NMR spectrum (376MHz) of C 58 F 17 CF 3 (1).

11. nine-peak 19 F NMR spectrum See ref 19

12. C 60 F 17 CF 3 R. Taylor, J. Chem. Soc. Perkin Trans. 2 2000, 2410 (2000).

14. Mechanism of formation of perfluoroalkyl derivatives J. Chem. Soc., Perkin Trans. 2, 2000, 2410–2414

15. Fig. 5. (Left) Comparison of the chemical shifts for C 58 F 17 CF 3 (top) and C 58 F 18 (bottom).

16. Conclusion 1. both 1 and 2 appear to be as stable as their C 60 counterparts, suggesting that further chemistry of C 58 ([58]quasi-fullerene) is in prospect. 2. The HPLC retention times of these C 58 compounds are ca. twice those for the corresponding C60 compounds (under conditions detailed above), which may help in identifying further C 58 derivatives.