Arylation of [60]fullerene via electrophilic aromatic substitution involving the electrophile C60Cl6: frontside nucleophilic substitution of fullerenes

Electrophilic Aromatic Substitution by the Fluorofullerene C60F18

“…For example, previously no reaction was observed between mesitylene and C 60 Cl 6 . [8] However, the smaller size of fluorine reduces this problem and ortho substitution occurs here in reaction with toluene, biphenyl, diphenyl ether, and surprisingly, at the 1-position of naphthalene. Interactions between aryl groups and fluorine atoms on the cage: The mono-substitution product obtained from reaction at the 1-position of naphthalene showed in the 1 H NMR spectrum, a 2.8 Hz coupling of the H-8 peri-hydrogen atom to the adjacent fluorine atom on the cage.…”

“…The structure of C 60 F 17 (1-naphthyl) ( Figure 5) was confirmed by EI mass, 1 H, and 19 F NMR spectra (see Experimental Section). The mass spectrum (see Figure 10) differs from that of the 2-naphthyl isomer, in the presence of the 1150 amu peak due to HF elimination of H 8 Fluoranthene: This gave both mono-(1244 amu) and bis-(1426 amu) substitution products. The NMR spectra were in each case very complicated as expected since there are two sites each more reactive than the 1-position of naphthalene, and two each more reactive than the 2-position of naphthalene.…”

“…[6] This led to isolation and characterisation of compounds such as, C 60 Ar 5 Cl and C 60 Ph 5 H, [7,8] C 60 Ph 4 and C 60 Ph 2 , [9] a phenylated isoquinolino [3,4:1,2][60]fullerene, [10] benzo [b]furano[60]-and [70]fullerenes, [11] C 70 Ph 10 and C 70 Ph 8 , [12] C 70 Ph 9 OH, [13] and two [70]fullerendiol isomers, C 70 Ph 8 (OH) 2 . [14] The use of a fluorofullerene as an electrophile has been reported in one study only, involving the FeCl 3 -catalysed reaction of C 60 F 18 with benzene, which produced the triphenyl derivative ("triumphene") (1, Ar= Ph).…”

Convenient Fullerene Derivatization: A Solvothermal Method for the Acquisition of Polyarylated Fullerenes with Aryl Group Number Above Five

“…There are many approaches for fullerene multiple modifications [4,5], among them it is an efficient way by using chlorofullerene C 60 Cl 6 as precursor to get useful fullerene derivatives [6][7][8][9][10]. Friedel-Crafts reaction of fullerene or chlorofullerenes is a facile method for bulk production of multi-functional fullerenes because of simplicity and low cost [6,11,12]. But C 60 Ar n (n > 5, Ar = aryl group) are always minor products either the substrate is C 60 or C 60 Cl 6 , which blocks their application investigation.…”

“…Richly functionalized fullerenes not only furnish aesthetically appealing molecular entities, but also show even better promising applications than pure parents or mono-functionalized ones for improved biological compatibility and photoelectric properties [1][2][3]. There are many approaches for fullerene multiple modifications [4,5], among them it is an efficient way by using chlorofullerene C 60 Cl 6 as precursor to get useful fullerene derivatives [6][7][8][9][10]. Friedel-Crafts reaction of fullerene or chlorofullerenes is a facile method for bulk production of multi-functional fullerenes because of simplicity and low cost [6,11,12].…”