Fullerene, chlorinated

The only reported X-ray structure of a it-bonded diiodine exists in the 12/coronene associate [75], which shows the I2 to be located symmetrically between the aromatic planes and to form infinite donor/acceptor chains. -Coordination of diiodine over the outer ring in this associate is similar to that observed in the bromine/arene complexes (vide supra), and the I - C separation of 3.20 A is also significantly contracted relative to the stun of their van der Waals radii [75]. For the highly reactive dichlorine, only X-ray structures of its associates are observed with the n-type coordination to oxygen of 1,4-dioxane [76], and to the chlorinated fullerene [77]. 

Treatment of chlorinated fullerenes, such as 12a-d, 14, and 19, with AICI3 or FeCh in the presence of an aromatic compound gave the substitution products, as a result of the abstraction of a chloride ion and the subsequent electrophilic attack of the intermediate cation to the aromatic ring (Scheme 9.13) [21, 31]. The chloride... 

Another exciting developing field is in material science. Chlorination and bromination of fullerenes (refs. 18,19) and solid state bromination of polyacetylenes (refs. 20,21) and of polybutadienes (ref. 22) are typical examples. 

Chlorine (Cl), 6 130-211 9 280. See also Inorganic chlorine XeCl laser addition to fullerene, 12 240-241 analytical methods, 6 202 bleaching agent, 4 50 capacities of facilities, 6 193-198t catalyst poison, 5 257t chemical properties, 6 133-138 diffusion coefficient for dilute gas in water at 20° C, l 67t diffusion coefficient in air at 0° C, l 70t for disinfection, 8 605 economic aspects, 6 188-202 electrolytic preparation/production of, 12 759 16 40 end uses, 6 134-135 in fused quartz manufacture, 22 413 generating from hydrogen chloride, 13 833... 

Prakash, Chlorination and bromination of fullerenes. Nucleophilic methoxylation of polychlorofullerenes and their aluminum trichloride catalyzed friedel-crafts reaction with aromatics to polyarylfullerenes, Journal of American Chemical Society, vol. 113, pp. 9385-9387,1991. 

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],... 

Chlorofullerenes are sensitive to hydrolysis and readily react with nucleophiles [73]. A mixture of polychlorofullerenes reacts with potassium mefhanolate or benzene to form polymethoxylated or polyphenylated fullerenes in which aU of the chlorine atoms are replaced [74]. So far, only CjoClg has been prepared in high... 

Gravimetric and elemental analysis lead to the following bruto-formula for the products of fullerene chlorination C6oCln (n=2 8). The broad bands in IR spectra (Fig. 2) close to characteristic vibrations for C-Cl bonds (frequencies 885, 850 and 808 cm"1) evidenced the presence of the mixture different isomers in the sample... 

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