Fullerenol

Chiang L Y, Wang L Y, Tseng S M, Wu J S and Heieh K H 1994 Fullerenol derived urethane-oonneoted polyether dendritio polymers J. Chem. Soc., Chem. Commun. 2675-6... 

Chiang L Y, Lu F-J and Lin J-T 1995 Free radioal soavenging aotivity of water-soluble fullerenols J. Chem. See., Chem. Commun. 1283-4... 

H. Kato, A. Yashiro, A. Mizuno, Y. Nishida, K. Kobayashi, and H. Shinohara, Syntheses and biological evaluations of a-D-mannosyl [60]fullerenols, Bioorg. Med. Chem. Lett., 11 (2001) 2935-2939. 

A characteristic reaction of the alkylated C60 chlorides thus prepared is clean hydrolysis to give fullerenols in the presence of silica gel. Most simply this could be carried out by passing a solution of the chloride through a column of silica gel. This can be explained via a silica gel-assisted ionization of the chloride and trapping of the intermediate cation by water present in the reaction system. In all cases, the product was the 1,4 isomer (Figure 5). 

Chiang LY, Lu F-J, Lin J-T (1995) Free radical scavenging activity of water-soluble fullerenols. Chem. Commun. 1 1283-1284. 

Chiang LY, Bhonsle JB, Wang L, Shu SF, Chang TM, Hwu JR (1996) Efficient one-flask synthesis of water-soluble [60]fullerenols. Tetrahedron 52 4963 1972. 

Lai HS, Chen WJ, Chiang LY (2000a) Free radical scavenging activity of fullerenol on the ischemia-reperfusion intestine in dogs. World J. Surg. 24 450 154. 

Mirkov SM, Djordjevic AN, Andric NL, Andric SA, Kostic TS, Bogdanovic GM, Vojinovic-Miloradov MB, Kovacevic RZ (2004) Nitric oxide-scavenging activity of polyhydroxylated fullerenol, C60(OH)24. Nitric Oxide 11 201-207. 

Anderson SA, Lee KK, Frank JA (2006) Gadolinium-fullerenol as a paramagnetic contrast agent for cellular imaging. Invest. Radiol. 41 332-338. 

Cgg reacts with sulfuric/nitric acid, and subsequent hydrolysis of the intermediates with aqueous base affords fullerenols (Scheme 8.10) [81-84]. Either nitric acid itself or nitric acid produced in situ from potassium nitrate and fuming sulfuric acid can be used. 

Flectrophilic addition of polychloroalkanes such as, e.g., chloroform or 1,1,2,2-tetrachloroethane to Cjq with AICI3 in a 100-fold excess gives the monoadduct with a 1,4-addition pattern (Scheme 8.12) [93, 94], The reaction proceeds via a CjqR cation (19, Scheme 8.12) that is stabilized by the coordination of a chlorine atom to the cationic center. The cation is trapped by Cl to give the product 20. The chloroalkyl fullerenes can be readily hydrolyzed to form the corresponding fullerenol 21. This fullerenol can be utilized as a proper precursor for the cation, which is easily obtained by adding triflic acid. The stability of CjqR is similar to tertiary alkyl cations such as the tert-butyl-cation [95],... 

Figure 14. UV-vis-NIR absorption spectra of CI2CH-C70 generatedfrom the corresponding fullerenols in CFsSOsH at room temperature. Cell length 1 cm. (a) 1017 xlO M. (b) 5.90 x 10 M. (Reproduced with permission from reference 15. Copyright 2005 Wiley-VCH.)...

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