Method of synthesis of water soluble fullerene polyacids using a macrocyclic malonate reactant

• US 6,538,153 B1
• Filed: 09/25/2001
• Issued: 03/25/2003
• Est. Priority Date: 09/25/2001
• Status: Expired due to Term

• Current Assignee: Luna Labs USA LLC
• Original Assignee: C Sixty Incorporated
• Inventors: Reuther, Uwe, Hirsch, Andreas
• Primary Examiner(s): Lambkin, Deborah C.
• Application Number:
  US09/962,492
• Time in Patent Office: 546 Days
• Field of Search: 560/82, 562/405, 549/263
• US Class Current: 560/82
• CPC Class Codes: C07C 51/09 from carboxylic acid esters or lactones
• CPC Class Codes: C07C 61/39 containing six-membered aromatic rings
• CPC Class Codes: Y10S 977/734 Fullerenes, i.e. graphene-based structures, such as nanohorns, nanococoons, nanoscrolls or fullerene-like structures, e.g. WS2 or MoS2 chalcogenide nanotubes, planar C3N4, etc.
• CPC Class Codes: Y10S 977/788 Of specified organic or carbon-based composition
• CPC Class Codes: Y10S 977/89 Deposition of materials, e.g. coating, cvd, or ald
• CPC Class Codes: Y10S 977/896 Chemical synthesis, e.g. chemical bonding or breaking

Abstract

A method for synthesizing compounds of the formula

where C₆₀ is a C₆₀ fullerene. The method comprises the steps of forming a macrocyclic malonate compound of the formula

where each Z is the same or different and is a straight-chain or branched-chain aliphatic radical having from 1-30 carbon atoms which may be unsubstituted or monosubstituted or polysubstituted by identical or different substitutents, in which radicals up to every third CH₂ unit can be replaced by O or NR where R is alkyl having 1-20 carbon atoms or a chain containing unsubstituted or substituted aryl or other cyclic groups and n is an integer from 2 to 10; reacting said macrocyclic malonate compound with C₆₀ to form an adduct of the formula

where the Z radicals are linked together to form said macrocycle adduct; and hydrolyzing said macrocycle adduct to form a compound of the formula

Claims

1. A method for synthesizing compounds of the formula

where C₆₀ is a C₆₀ fullerene, comprising the steps of:

(a) forming a macrocyclic malonate compound of the formula

 

where each Z is the same or different and is a straight-chain or branched-chain aliphatic radical having from 1-30 carbon atoms which may be unsubstituted or monosubstituted or polysubstituted by identical or different substitutents, in which radicals up to every third CH₂ unit can be replaced by O or NR where R is alkyl having 1-20 carbon atoms or a chain containing unsubstituted or substituted aryl or other cyclic groups and n is an integer from 2 to 10;

(b) reacting said macrocyclic malonate compound with C₆₀ to form a macrocycle adduct of the formula

 

where the Z radicals are linked together to form said macrocycle adduct; and

(c) hydrolyzing said macrocycle adduct to form a compound of the formula

2. A method as recited in claim 1 wherein n is 2.

3. A method as recited in claim 1 wherein n is 3.

4. A method as recited in claim 1 wherein Z is a diol.

5. A method as recited in claim 1 wherein each Z is an alkanediol containing 8-10 carbon atoms.

6. A method as recited in claim 1 wherein Z is octanediol.

7. A method for synthesizing compounds of the formula

where C₆₀ is a C₆₀ fullerene, comprising the steps of:

(a) reacting a macrocyclic malonate compound of the formula

 

where each Z is the same or different and is a straight-chain or branched-chain, aliphatic radical having from 1-30 carbon atoms which may be unsubstituted or monosubstituted or polysubstituted by identical or different substitutents, in which radicals up to every third CH₂ unit can be replaced by O or NR where R is alkyl having 1-20 carbon atoms or a chain containing unsubstituted or substituted aryl or other cyclic groups and n is an integer from 2 to 10 with C₆₀ to form a macrocycle adduct of the formula

 

where the Z radicals are linked together to form said macrocycle adduct; and

(b) hydrolyzing said macrocycle adduct to form a compound of the formula

8. A method as recited in claim 7 wherein n is 2.

9. A method as recited in claim 7 wherein n is 3.

10. A method as recited in claim 7 wherein Z is a diol.

11. A method as recited in claim 7 wherein each Z is an alkanediol containing 8-10 carbon a toms.

12. A method as recited in claim 7 wherein Z is octanediol.

13. A method for synthesizing compounds of the formula

where C₆₀ is a C₆₀ fullerene, comprising the step of hydrolyzing a macrocycle adduct of the formula

where the Z radicals are linked together to form said macrocycle adduct to form a compound of the formula

14. A method as recited in claim 13 wherein n is 2.

15. A method as recited in claim 13 wherein n is 3.

16. A method as recited in claim 13 wherein Z is a diol.

17. A method as recited in claim 13 wherein each Z is an alkanediol containing 8-10 carbon atoms.

18. A method as recited in claim 13 wherein Z is octanediol.