Nitrogen-containing aromatic compounds and metal complexes

Patent metadata

Field	Value
Publication number	US-10392395-B2
Application number	US-201013504820-A
Country	US
Kind code	B2
Filing date	Oct 29, 2010
Priority date	Oct 30, 2009
Publication date	Aug 27, 2019
Grant date	Aug 27, 2019

Abstract

To provide nitrogen-containing aromatic compounds with excellent oxygen reduction activity, metal complexes containing them, and catalysts and electrodes employing the same, the present invention provides an aromatic compound satisfying the following conditions (a) and (b):
(a) It has 2 or more structures surrounded by at least 4 coordinatable nitrogen atoms (which structures may be the same or different), (b) At least one of the nitrogen atoms composing the structure is a nitrogen atom in a 6-membered nitrogen-containing heterocyclic ring.

First claim

The invention claimed is:

1. An aromatic compound comprising 2 or more covalently-bound sections, the aromatic compound containing no metal atoms, satisfying the following conditions (a) and (b):
(a) individually, each of the 2 or more sections, which may be the same or different, includes at least 4 coordinatable nitrogen atoms, and the at least 4 coordinatable nitrogen atoms in each individual section are coordinatable with a single metal atom within each individual section,
(b) at least one of the nitrogen atoms in each individual section is a nitrogen atom in a 6-membered nitrogen-containing heterocyclic ring,
wherein the sections are selected from the group consisting of sections represented by the following formulae:

wherein

 represents a bond in an aromatic ring;
wherein each P 1A , P 1B and P 1C is part of a first polycyclic aromatic heterocyclic ring comprising two 6-membered aromatic rings, at least one of which is a heterocyclic ring; each P 2A , P 2B and P 2C is part of a second polycyclic aromatic heterocyclic ring comprising two 6-membered aromatic rings, at least one of which is a heterocyclic ring; each W 1A and W 1B is part of a first 5-membered heterocyclic ring; and each W 2A and W 2B is part of a second 5-membered heterocyclic ring; and wherein hydrogens therein may be substituted with halogeno, hydroxy, carboxyl, mercapto, sulfonic acid, nitro, amino, cyano, phosphonic acid, silyl substituted with C 1-4 alkyl, C 1-50 straight-chain or branched alkyl, C 3-50 cyclic alkyl, alkenyl, alkynyl, alkoxy, C 6-60 aryl, C 7-50 aralkyl, or monovalent heterocyclic groups, and
wherein:
W 1A and W 1B can form a 5-membered ring with each other;
W 2A and W 2B can form a 5-membered ring with each other;
P 1A and P 1B can form a 6-membered ring with each other;
P 1B and P 1C can form a 6-membered ring with each other;
P 2A and P 2B can form a 6-membered ring with each other;
P 2B and P 2C can form a 6-membered ring with each other; and
P 1C and P 2A can form a 6-membered ring with each other.

2. The aromatic compound according to claim 1 , wherein the ratio of the total mass of nitrogen atoms with respect to the total mass of carbon atoms in the aromatic compound is greater than 0 and no greater than 1.1.

3. A metal complex having a metal atom or metal ion, and a ligand comprising the aromatic compound according claim 1 .

4. The metal complex according to claim 3 , wherein the metal atom or metal ion is a transition metal atom or its ion, from between period 4 and period 6 of the Periodic Table.

5. A composition comprising the aromatic compound according to claim 1 , and a carbon particle, a C 60 fullerene, a C 70 fullerene, a carbon nanotube, a carbon nanohorn, or a carbon fiber, and/or polymer material.

6. A catalyst comprising the aromatic compound according to claim 1 .

7. An electrode comprising the aromatic compound according to claim 1 .

8. An electrode catalysts for fuel cell comprising the aromatic compound according to claim 1 .

9. A polymer electrolyte fuel cell using the electrode catalysts for fuel cell according to claim 8 .

10. The polymer electrolyte fuel cell according to claim 9 , wherein a polymer electrolyte membrane of the polymer electrolyte fuel cell is the one having proton conductivity.

11. The polymer electrolyte fuel cell according to claim 9 , wherein a polymer electrolyte membrane of the polymer electrolyte fuel cell is the one having anion conductivity.

Assignees

• Koshino Nobuyoshi
• Higashimura Hideyuki
• Muellen Klaus
• Von Malotki Christian
• Su Qi
• Baumgarten Martin
• Norouzi Arasi Hassan
• Arnold Lena
• Liu Ruili
• Sumitomo Chemical Co
• Max Planck Gesellschaft

Inventors

• Koshino Nobuyoshi
• Higashimura Hideyuki
• Muellen Klaus
• Von Malotki Christian
• Su Qi
• Baumgarten Martin
• Norouzi-Arasi Hassan
• Arnold Lena
• Liu Ruili

Classifications

• H01M8/1007

  with both reactants being gaseous or vaporised (H01M8/12 takes precedence) · CPC title

• H01M4/9008

  Organic or organo-metallic compounds · CPC title

• C07D471/22

  in which the condensed systems contains four or more hetero rings · CPC title

• B01J2531/72

  Manganese · CPC title

• B01J2231/62

  Reductions in general of inorganic substrates, e.g. formal hydrogenation, e.g. of N2 · CPC title