Method for producing fullerene derivative
This method for producing a fullerene derivative is a method for producing a fullerene derivative having a partial structure shown by formula (1) by reacting a predetermined halogenated compound and two carbon atoms adjacent to each other for forming a fullerene skeleton in a mixed solvent of an aromatic solvent and an aprotic polar solvent having a C═O or S═O bond in the presence of at least one metal selected from the group comprising manganese, iron, and zinc; (in formula (1), C* are each carbon atoms adjacent to each other for forming a fullerene skeleton, A is a linking group having 1-4 carbon atoms for forming a ring structure with two C*, in which a portion thereof may be a substituted or condensed group).
1. A method for producing a fullerene derivative having a partial structure represented by Formula (1), by reacting two carbon atoms adjacent to each other for forming a fullerene skeleton with a halogenated compound represented by Formula (2) in a mixed solvent of an aromatic solvent and an aprotic polar solvent having a C═O or S═O bond in the presence of at least one metal selected from the group consisting of manganese, iron and zinc:
(in Formula (1), C* each represent carbon atoms adjacent to each other for forming a fullerene skeleton, A represents a linking group with 1 to 4 carbon atoms for forming a ring structure or a functional group in which the linking group is partially substituted or condensed)
(in Formula (2), A represents a linking group with 1 to 4 carbon atoms or a functional group in which the linking group is partially substituted or condensed, and each X independently represents a halogen atom).
2. The method for producing a fullerene derivative according to claim 1 , wherein the linking group with 1 to 4 carbon atoms for A in Formulas (1) and (2) is partially substituted by an aromatic group, a heteroaromatic group, an alkoxycarbonyl group or an alkylidene group.
3. The method for producing a fullerene derivative according to claim 1 , wherein the linking group with 1 to 4 carbon atoms for A in Formulas (1) and (2) partially forms a condensed-ring structure or a polycyclic structure comprising an aromatic ring or a heteroaromatic ring with an aromatic ring or a heteroaromatic ring.
4. The method for producing a fullerene derivative according to claim 1 , wherein the aprotic polar solvent is one or more of the group consisting of dimethyl sulfoxide (DMSO) and dimethylformamide (DMF).
5. The method for producing a fullerene derivative according to claim 1 , wherein the aromatic solvent is o-dichlorobenzene.
6. The method for producing a fullerene derivative according to claim 1 , wherein the halogen atom (X) is Br.
7. The method for producing a fullerene derivative according to claim 1 , wherein the metal is Mn, and the aprotic polar solvent is DMF.
8. The method for producing a fullerene derivative according to claim 1 , wherein the metal is Fe, and the aprotic polar solvent is DMSO.
9. The method for producing a fullerene derivative according to claim 1 , wherein the metal is Mn or Zn, and the aprotic polar solvent is DMSO.