Method Of Preparing Macrocylic Metal Cyanine Compound

• US 20090240050A1
• Filed: 05/31/2009
• Published: 09/24/2009
• Est. Priority Date: 08/09/2004
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Hall, Lachlan Everett, Silverbrook, Kia, Vonwiller, Simone Charlotte, Starling, Scott Matthew, Fielder, Simon, Lapstun, Paul, Ridley, Damon Donald, Gonzaga, Graciel
• Granted Patent: US 7,834,175 B2
• Time in Patent Office: Days
• US Class Current: 540/465
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C09B 47/0675 having oxygen or sulfur linked directly to the skeleton
• CPC Class Codes: C09D 11/328 characterised by dyes

Abstract

A method of preparing a macrocyclic metal cyanine. The method comprises the step of providing a corresponding macrocyclic metal-free cyanine compound dissolved in a solvent and adding a metal reagent thereto. The metal reagent is highly soluble in the solvent and typically comprises one or more organic ligands.

Claims

1. A method of preparing a macrocyclic metal cyanine, said method comprising the step of providing a corresponding macrocyclic metal-free cyanine compound dissolved in a solvent and adding a metal reagent thereto, said metal reagent being highly soluble in said solvent, wherein the macrocyclic metal cyanine is of formula (I):

2. The method of claim 1, wherein the oxidation state of the metal in said metal reagent matches the oxidation state of the metal in said macrocyclic metal cyanine.

3. The method of claim 1, wherein said metal reagent comprises one or more ligands for providing said solubility in said solvent.

4. The method of claim 3, wherein said one or more ligands are selected from the group consisting of:

acetylacetonate (acac), acetate and C_1-8 alkoxide.

5. The method of claim 1, wherein the metal is vanadium.

6. The method of claim 1, wherein the metal reagent is VO(acac)₂.

7. The method of claim 1 comprising the further step of sulfonating said macrocylic metal cyanine of formula (I).

8. The method of claim 7, wherein Q¹, Q², Q³ and Q⁴ are selected from an arylene or heteroarylene group of the formula:

9. The method of claim 8, wherein R¹ and R² are selected from the group consisting of:

hydrogen and C_1-8 alkoxy.

10. The method of claim 8, wherein n is 0.