Composite of organic compound and copper nanoparticles, composite of organic compound and copper(i) oxide nanoparticles, and methods for producing the composites

A composite of an organic compound and copper nanoparticles, the composite comprising a thioether-containing organic compound (A) represented by a general formula (1) below and copper nanoparticles (B)

• X—(OCH2CHR1)n—O—CH2—CH(OH)—CH2—S—Z (1)
• [in the formula (1), X represents a C1 to C8 alkyl group;
• R1 represents a hydrogen atom or a methyl group;
• n represents a repeating number, an integer of 2 to 100;
• R1 is independent between repeating units and may be the same or different;
• and Z represents a C2 to C12 alkyl group, an allyl group, an aryl group, an arylalkyl group, —R2—OH, —R2—NHR3, or —R2—(COR4)m (where R2 represents a C1 to C4 saturated hydrocarbon group;
• R3 represents a hydrogen atom, a C2 to C4 acyl group, a C2 to C4 alkoxycarbonyl group, or a benzyloxycarbonyl group that may optionally have, as a substituent on the aromatic ring, a C1 to C4 alkyl group or a C1 to C8 alkoxy group;
• R4 represents a hydroxy group, a C1 to C4 alkyl group, or a C1 to C8 alkoxy group;
• and m represents 1 to 3)].

A composite of an organic compound and copper(I) oxide nanoparticles, the composite comprising a thioether-containing organic compound (A) represented by a general formula (1) below and copper(I) oxide nanoparticles (C)

• X—(OCH2CHR1)n—O—CH2—CH(OH)—CH2—S—Z (1)
• [in the formula (1), X represents a C1 to C8 alkyl group;
• R1 represents a hydrogen atom or a methyl group;
• n represents a repeating number, an integer of 2 to 100;
• R1 is independent between repeating units and may be the same or different;
• and Z represents a C2 to C12 alkyl group, an allyl group, an aryl group, an arylalkyl group, —R2—OH, —R2—NHR3, or —R2—(COR4)m (where R2 represents a C1 to C4 saturated hydrocarbon group;
• R3 represents a hydrogen atom, a C2 to C4 acyl group, a C2 to C4 alkoxycarbonyl group, or a benzyloxycarbonyl group that may optionally have, as a substituent on the aromatic ring, a C1 to C4 alkyl group or a C1 to C8 alkoxy group;
• R4 represents a hydroxy group, a C1 to C4 alkyl group, or a C1 to C8 alkoxy group;
• and m represents 1 to 3)].

A method for producing a composite of an organic compound and copper nanoparticles, the method comprising:

• in the presence of a thioether-containing organic compound (A) represented by a general formula (1) below
• X—(OCH2CHR1)n—O—CH2—CH(OH)—CH2—S—Z (1)
• [in the formula (1), X represents a C1 to C8 alkyl group;
• R1 represents a hydrogen atom or a methyl group;
• n represents a repeating number, an integer of 2 to 100;
• R1 is independent between repeating units and may be the same or different;
• and Z represents a C2 to C12 alkyl group, an allyl group, an aryl group, an arylalkyl group, —R2—OH, —R2—NHR3, or —R2—(COR4)m (where R2 represents a C1 to C4 saturated hydrocarbon group;
• R3 represents a hydrogen atom, a C2 to C4 acyl group, a C2 to C4 alkoxycarbonyl group, or a benzyloxycarbonyl group that may optionally have, as a substituent on the aromatic ring, a C1 to C4 alkyl group or a C1 to C8 alkoxy group;
• R4 represents a hydroxy group, a C1 to C4 alkyl group, or a C1 to C8 alkoxy group;
• and m represents 1 to 3)]
• (i) a step of mixing a divalent copper-ion compound with a solvent;
• and
• (ii) a step of reducing the copper ions to zero-valent copper nanoparticles (B).

A method for producing a composite of an organic compound and copper(I) oxide nanoparticles, the method comprising:

• in the presence of a thioether-containing organic compound (A) represented by a general formula (1) below
• X—(OCH2CHR1)n—O—CH2—CH(OH)—CH2—S—Z (1)
• [in the formula (1), X represents a C1 to C8 alkyl group;
• R1 represents a hydrogen atom or a methyl group;
• n represents a repeating number, an integer of 2 to 100;
• R1 is independent between repeating units and may be the same or different;
• and Z represents a C2 to C12 alkyl group, an allyl group, an aryl group, an arylalkyl group, —R2—OH, —R2—NHR3, or —R2—(COR4)m (where R2 represents a C1 to C4 saturated hydrocarbon group;
• R3 represents a hydrogen atom, a C2 to C4 acyl group, a C2 to C4 alkoxycarbonyl group, or a benzyloxycarbonyl group that may optionally have, as a substituent on the aromatic ring, a C1 to C4 alkyl group or a C1 to C8 alkoxy group;
• R4 represents a hydroxy group, a C1 to C4 alkyl group, or a C1 to C8 alkoxy group;
• and m represents 1 to 3)]
• (i) a step of mixing a divalent copper-ion compound with a solvent;
• and
• (ii′) a step of reducing the copper ions to monovalent copper(I) oxide nanoparticles (C).