Conjugated polymers provided with at least one molecular imprinted polymer and a method for their preparation via conjugated macro-iniferters

• US 7,649,048 B2
• Filed: 10/11/2005
• Issued: 01/19/2010
• Est. Priority Date: 10/13/2004
• Status: Expired due to Fees

• Current Assignee: Universiteit Hasselt
• Original Assignee: IMEC International, Universiteit Hasselt
• Inventors: Lutsen, Laurence, Vanderzande, Dirk
• Primary Examiner(s): ZEMEL, IRINA SOPJIA
• Application Number:
  US11/247,397
• Publication Number:
  US 20060079648A1
• Time in Patent Office: 1,561 Days
• Field of Search: 525 67- 69, 525/64, 528/390, 528/391
• US Class Current: 525/69
• CPC Class Codes: B01J 20/268 Polymers created by use of a template, e.g. molecularly imprinted polymers
• CPC Class Codes: C08F 289/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
• CPC Class Codes: C08F 291/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 51/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds

Abstract

The present invention provides a conjugated polymer with provided thereon at least one molecular imprinted polymer (MIP) and a method for preparing such a polymer. The conjugate polymer provided with at least one MIP according to the invention combines both transducer properties and selectivity properties in one single material. Therefore, it is particularly suitable for use in chemo- or bio-sensors. Furthermore, the conjugate polymer provided with at least one MIP may be used in electronic devices and in chromatography, molecular recognition, selective sample enrichment or in catalysis.

Claims

1. A molecularly imprinted conjugated polymer comprising:

a conjugated polymer backbone; and

at least one molecularly imprinted polymer grafted on the conjugated polymer backbone, the molecularly imprinted polymer comprising cavities, wherein the cavities have a shape, a size, and functional groups dependent on a template molecule used during a polymerization reaction for forming the molecularly imprinted conjugated polymer,

wherein the molecularly imprinted conjugated polymer exhibits predetermined selective molecular recognition in combination with signal transducing properties achieved by electrical conductivity and fluorescence properties of the conjugated polymer backbone.

2. The molecularly imprinted conjugated polymer according to claim 1, having a selectivity functionality and a transducer functionality.

3. The molecularly imprinted conjugated polymer according to claim 1, wherein the molecularly imprinted conjugated polymer is a poly(p-phenylene vinylene) derivative.

4. The molecularly imprinted conjugated polymer according to claim 1, wherein the molecularly imprinted conjugated polymer is an OC1C10-PPV derivative.

5. The molecularly imprinted conjugated polymer according to claim 1, wherein the molecularly imprinted conjugated polymer is a derivative of a conjugated polymer which comprises at least one unit selected from the group consisting of thiophene, fluorene, arylene, heteroarylene, vinylene, and combinations thereof.

6. The molecularly imprinted conjugated polymer according to claim 1, wherein the molecularly imprinted conjugated polymer is a poly-(3-hexylthiophene) derivative.

7. The molecularly imprinted conjugated polymer according to claim 1, wherein the conjugated polymer backbone is derived from a dithiocarbamate functionalized monomer of general formula (1):

8. The molecularly imprinted conjugated polymer according to claim 7, wherein R₁ and R₂ are independently selected from the group consisting of methyl, ethyl, and isopropyl.

9. The molecularly imprinted conjugated polymer according to claim 7, wherein Ar is selected from the group consisting of 2,6-naphthalenediyl;

1,4-naphthalenediyl;

1,4-anthracenediyl;

2,6-anthracenediyl; and

9,10-anthracenediyl.

10. The molecularly imprinted conjugated polymer according to claim 7, wherein Ar is 1,4-phenylene.

11. The molecularly imprinted conjugated polymer according to claim 7, wherein Ar is 2,5-thienylene.

12. The molecularly imprinted conjugated polymer according to claim 1, having an average molecular weight of not higher than about 1000 kD.

13. The molecularly imprinted conjugated polymer according to claim 1, having an average molecular weight of from about 40 kD to about 1000 kD.

14. The molecularly imprinted conjugated polymer according to claim 1, having an average molecular weight of not higher than about 300 kD.

15. The molecularly imprinted conjugated polymer according to claim 1, having an average molecular weight of from about 40 kD to about 300 kD.

16. The molecularly imprinted conjugated polymer according to claim 1, wherein a ratio between the conjugated polymer backbone and the molecularly imprinted polymer is about 50/50.

17. The molecularly imprinted conjugated polymer according to claim 1, wherein an amount of initiator groups remaining in the molecularly imprinted conjugated polymer is less than about 10%.

18. The molecularly imprinted conjugated polymer according to claim 1, wherein an amount of initiator groups remaining in the molecularly imprinted conjugated polymer is less than about 5%.

19. The molecularly imprinted conjugated polymer according to claim 1, wherein an amount of initiator groups remaining in the molecularly imprinted conjugated polymer is less than about 1%.

20. The molecularly imprinted conjugated polymer according to claim 1, wherein the conjugated polymer backbone is of general formula:

21. The molecularly imprinted conjugated polymer according to claim 1, of general formula: