Method for functionalizing a solid substrate, other than a substrate made of gold, via specific chemical compounds

Patent metadata

Field	Value
Publication number	US-10002769-B2
Application number	US-201214349853-A
Country	US
Kind code	B2
Filing date	Oct 5, 2012
Priority date	Oct 6, 2011
Publication date	Jun 19, 2018
Grant date	Jun 19, 2018

Abstract

The invention relates to a method for functionalizing an electrically conductive substrate, which is not a substrate made of gold, via a layer of chemical compounds, said method comprising the following steps:
a step in which the electrically conductive substrate is placed in contact with chemical compounds comprising at least a disulfide terminal group; a step in which the disulfide terminal group of said chemical compounds is electro-oxidized, causing said chemical compounds to form a layer at the surface of the electrically conductive substrate.

First claim

The invention claimed is:

1. A method for functionalizing an electrically conductive substrate via a layer comprising a chemical compound, the substrate being a substrate made of a material selected from the group consisting of carbon, platinum, an indium-tin oxide and nickel, comprising:
contacting the electrically conductive substrate with a chemical compound comprising at least a disulfide terminal group, said chemical compound satisfies formula (I):

wherein:
X is a charge storage group, which is a polyazacycloalkane group complexed with at least a metal element, said polyazacycloalkane group being a tetrazacycloalkane group selected from the group consisting of formula (II), formula (III) and formula (IV):

wherein:
R 1 , R 2 , R 3 and R 4 represent, independently of each other, an alkyl, aryl, alkylaryl group, a halogen atom, an (alkyl)metallocene group, wherein the alkyl, aryl, alkylaryl, (alkyl)metallocene group may be perfluorinated;
M is a metal element having at least two degrees of oxidation;
braces indicating the spot through which said tetraazacycloalkane group is bound to the disulfide group via a spacer group;
L is a single bond or an organic spacer group;
Z is a cyclic disulfide group; and
n is a whole number ranging from 1 to 6; and
electro-oxidizing the cyclic disulfide terminal group of said chemical compounds, causing said chemical compounds to form a layer at the surface of the electrically conductive substrate.

2. The method of claim 1 , wherein the tetraazacycloalkane group is of formula (II).

3. The method of claim 1 , wherein the tetraazacycloalkane group satisfies one of formula (V) and formula (VI):

wherein: M is a metal element having at least two degrees of oxidation; and
T represents a ferrocene group.

4. The method of claim 1 , wherein the metal element is a transition metal element.

5. The method of claim 4 , wherein the transition metal element is selected from the group consisting of Cr, Mn, Fe, Co, Ni, and Cu.

6. The method of claim 1 , wherein the metal element is copper.

7. The method of claim 1 , wherein said charge storage group and said disulfide terminal group are separated by an organic spacer group which is a hydrocarbon group, being in the form of a linear or branched chain, in which one or more bonding groups can be inserted.

8. The method of claim 7 , wherein the hydrocarbon group is an alkylene group, in which one or more bonding groups can be inserted.

9. The method of claim 7 , wherein the one or more bonding groups are selected from the group consisting of a —(C═O)— group, a —(C═O)O group, a —SO 2 group, and an amide group.

10. The method of claim 1 , wherein said charge storage group and said disulfide terminal group are separated by an organic spacer group satisfying the following fomula (VII):
—(CH 2 ) 4 —NH—CO—(CH 2 ) 4 —  (VII).

11. The method of claim 1 , wherein the disulfide group is a group of following formula (VIII):

12. The method of claim 1 , wherein the chemical compounds satisfy one of formula (IX) and formula (X):

wherein T represents a ferrocene group.

13. The method of claim 1 , wherein the tetraazacycloalkane group is of formula (III).

14. The method of claim 1 , wherein the tetraazacycloalkane group is of formula (IV).

Assignees

• Commissariat Energie Atomique
• Commissariat Energie Atomique

Inventors

• Jalaguier Eric
• Buckley Julien
• Chevalier Xavier
• Royal Guy

Classifications

• H10P95/50

  Alloying conductive materials with semiconductor bodies · CPC title

• H10P14/46 Primary

  using a liquid · CPC title

• H01L21/288 Primary

  Electricity · mapped topic

• C07D339/04

  having the hetero atoms in positions 1 and 2, e.g. lipoic acid · CPC title

• H01L21/244

  Electricity · mapped topic