Synthesis of metal cyanines

• US 7,550,585 B2
• Filed: 08/09/2004
• Issued: 06/23/2009
• Est. Priority Date: 08/09/2004
• Status: Expired due to Fees

• 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
• Primary Examiner(s): Wilson; James O.
• Assistant Examiner(s): Ward; Paul V.
• Application Number:
  US10/913,376
• Publication Number:
  US 20060030702A1
• Time in Patent Office: 1,779 Days
• Field of Search: 540/145
• US Class Current: 540/145
• 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 for preparing a macrocyclic metal cyanine, comprising the step of providing a macrocyclic metal-free cyanine precursor and inserting a metal therein using a metal reagent, wherein said metal reagent comprises at least one organic ligand.

Claims

1. A method for preparing a macrocyclic metal cyanine, comprising the step of providing a macrocyclic metal-free cyanine compound and inserting a metal therein using a metal reagent, wherein said metal reagent comprises at least one organic ligand, wherein said organic ligand is acetylacetonate (acac), acetate or C_1-8 alkoxide, and 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 the metal is vanadium.

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

5. The method of claim 1, wherein Q¹, Q², Q³ and Q⁴ are selected from an arylene or heteroarylene group of the formula:

6. The method of claim 5, wherein R¹ and R² are selected from hydrogen or C_1-8 alkoxy.

7. The method of claim 5, wherein W is selected from a substituent comprising a PEG chain;

a substituent comprising an ammonium group;

a substituent comprising an acid group, including salts thereof or a substituent comprising a sulfonamide group.

8. The method of claim 5, wherein W is —

SO₃H or a water-soluble salt thereof.

9. The method of claim 5, wherein M is Ti(A¹)(A²), Zr(A¹)(A²), V(A¹)(A²), Si(A¹)(A²), Ge(A¹)(A²), Ga(A¹), Al(A¹), Mn(A¹), Fe(A¹), Sn(A¹)(A²), or Pb(A¹)(A²).