Patent ID: 6448412
Filing Date: 2002-09-10
Classification: B82Y,C07C,C07D,C40B,G11C,Y10S

Abstract:
A method for the simultaneous synthesis of a multiplicity of different multiply-substituted fullerenes having the formula: wherein:Z1, Z2 and Z3 are absent or present, provided that at least one is present, and are independently selected from the group consisting of â€”CR1R2â€”, â€”CR1R2â€”CR3R4â€”, â€”NR1â€”, â€”Oâ€”CR1R2â€”, â€”Sâ€”CR1R2â€”, â€”NR1â€”CR2R3â€”, â€”R1R2Câ€”NR3â€”CR4R5â€”, â€”R1C&boxH;Nâ€”CR2R3â€”, â€”R1R2Câ€”NR3â€”NR4â€”, â€”R1R2Câ€”NR3â€”Oâ€”, â€”N&boxH;NR1â€”, â€”N&boxH;Nâ€”NR1â€”, â€”N&boxH;Nâ€”CR1R2â€”, â€”Oâ€”NR1â€”Oâ€”, â€”R1R2Câ€”Oâ€”CR3R4â€”, â€”R1R2Câ€”Oâ€”NR3â€”, â€”R1C&boxH;Nâ€”NR2â€”, â€”R1C&boxH;Nâ€”Oâ€”, â€”R1Nâ€”NR2â€”NR3â€”, â€”R1Nâ€”NR2â€”Oâ€”, â€”CR1R2â€”CR3R4â€”CR5R6â€”, â€”CR1R2â€”CR3&boxH;CR4â€”, â€”CR1R2â€”CR3R4â€”CR5CR6â€”CR7R8â€”, â€”CR1&boxH;R2â€”CR3R4â€”CR5R6â€”, â€”CR1R2â€”CR3&boxH;CR4â€”CR5R6â€”, â€”CR1&boxH;CR2â€”CR3&boxH;CR4â€” and â€”CR1R2â€”CR3&boxH;C&boxH;CR4â€” such that Z1, Z2 and Z3 are each attached to the carbon skeleton of the fullerene structure by two single bonds selected from the group consisting of a carbonâ€”carbon bond, a carbon-oxygen bond, a carbon-sulfur bond, and a carbon-nitrogen bond, the unsatisfied valences of each Z moiety being the location of those bonds; R1, R2, R3, R4, R5, R6, R7 and R8 are the same or different and are selected from the group consisting of hydrogen, oxygen lower alkyl, higher alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, carboxylic acids, carboxylic esters, alkylthio, thioalkyl, aryl, aryloxy, aralkyl, primary amine, secondary amine, amino acid side chains, and heterocycles, such that C together with any two R groups bonded thereto forms an oxo or thioxo group, hydrocarbon ring or heterocycle; Y1 and Y2 are absent or present, providing that at least one is present, and are selected from the group consisting of hydrogen, lower alkyl, higher alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, thioalkyl, aryl, aryloxy, aralkyl, primary amine, secondary amine, amino acid side chains, and heterocycles; 20(k1+k2) is 1 to n; and (m1+m2+m3) is 1 to n/2, with the limitation that 2(m1+m2+m3)+(k1+k2)&lE;n; or a salt or addition compound thereof;said method comprising the steps of: (a) reacting fullerenes of the formula Cn, wherein 201 or (ii) moieties selected from the group consisting of Y1, Y2, and Y1 and Y2, and (b) reacting said fullerene monoadducts with a plurality of second compounds selected from compounds which react with the fullerene monoadducts to form a plurality of fullerene diadducts, wherein the reaction adds to the fullerene monoadducts the other of (i) moieties Z1 or (ii) moieties selected from the group consisting of Y1, Y2, and Y1 and Y2 than was added in step (a), and (c) reacting said fullerene diadducts with plurality of third compounds is selected from compounds which react with the fullerene diadducts to form a plurality of fullerene triadducts, wherein the reaction adds to the fullerene diadducts moieties Z2.