Luminescent polymer particles

• US 7,462,325 B2
• Filed: 11/30/2001
• Issued: 12/09/2008
• Est. Priority Date: 11/30/2001
• Status: Expired due to Fees

• Current Assignee: Flir Detection, Inc. (Teledyne Technologies Incorporated)
• Original Assignee: Nomadics, Inc. (Teledyne Technologies Incorporated)
• Inventors: Chen, Wei, Deans, Robert, Hancock, Lawrence F.
• Primary Examiner(s): Cain; Edward J
• Application Number:
  US09/997,999
• Publication Number:
  US 20030134959A1
• Time in Patent Office: 2,566 Days
• Field of Search: 524/80, 436/172, 526/285, 422/82.05, 422/82.08, 252/301.35
• US Class Current: 422/82.05
• CPC Class Codes: C08G 61/02 Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
• CPC Class Codes: C08G 61/10 only aromatic carbon atoms, e.g. polyphenylenes

Abstract

This invention involves a series of articles, dispersions, compositions, methods, and kits. Several aspects of the invention involve dispersed particles made from polymers having a delocalized π-orbital backbone structure, as well as methods for making and using such particles. The delocalized π-orbital backbone allows the polymer to have a high degree of luminosity, useful in many embodiments of the invention. The polymers of this invention can also have bulky substituents to prevent intermolecular π-π interactions that can decrease luminosity. The polymer may also have charged side chains immobilized relative to the backbone, which can allow the polymer to be made into stably suspended micro- or nanoparticles dispersed in solution, sometimes with very narrow size distributions. In some embodiments, depending on the conditions used to synthesize and prepare the particles, the particles each consist of a single polymer molecule. Side groups, including biological, biochemical, or chemical molecules, can be attached to the polymer to provide additional functions, such as altering the luminosity of the polymer, or allowing the polymer to bind to certain molecules, such as in a chemical sensor or in a biological assay. As the binding of a molecule to a side group on the polymer can affect the structure of the polymer or alter the luminosity of the particle, the particles of the invention may be used, in certain embodiments, to detect the presence of single molecules.

Claims

1. The polymeric article, comprising:

a luminescent polymer in particulate form, wherein the luminescent polymer comprises a plurality of triple bonds and at least one aromatic group.

21. The polymeric article of claim 1, wherein the particle comprises a moiety that is able to become to a biological, biochemical, and/or chemical molecule.

23. The polymeric article of claim 21 wherein the luminescent polymer comprises the moiety that is able to become attached to a biological, biochemical, and/or chemical molecule so as to form, upon attachment, a particle comprising the luminescent polymer attached to the biological, biochemical, and/or chemical molecule.

24. The polymeric article of claim 23 further comprising:

the biological, biochemical, and/or chemical molecule attached to the luminescent polymer.

25. The polymeric article of claim 24, wherein the biological, biochemical, and/or chemical molecule is a nucleic acid molecule.

2. A polymeric article, comprising:

a luminescent polymer particle comprising a nucleic acid covalently attached to the luminescent polymer, wherein the luminescent polymer comprises a triple bond.

3. The polymeric article of claim 2, wherein the luminescent polymer comprises an iptycene moiety.

4. The polymeric article of claim 3, wherein the iptycene moiety comprises at least three arene planes.

5. The polymeric article of claim 4, wherein the iptycene moiety comprises at least five arene planes.

6. The polymeric article of claim 3, wherein the iptycene moiety is at least a portion of a repeat unit of the luminescent polymer.

7. The polymeric article of claim 2, wherein the luminescent polymer comprises a backbone.

8. The polymeric article of claim 7, wherein the backbone comprises a delocalized π

-electron bond.

9. The polymeric article of claim 7, wherein the backbone comprises a benzene ring.

10. The polymeric article of claim 9, wherein the benzene ring is at least a portion of a repeat unit of the backbone of the luminescent polymer.

11. The polymeric article of claim 9, wherein a pendant group is attached to the backbone via the benzene ring.

12. The polymeric article of claim 7, wherein the triple bond is at least a portion of a repeat unit of the luminescent polymer.

13. The polymeric article of claim 2, wherein the luminescent polymer comprises a plurality of triple bonds.

14. The polymeric article of claim 2, wherein the luminescent polymer comprises a copolymer formed from a plurality of monomers, wherein at least one monomer comprises a structure:

15. The polymeric article of claim 2, wherein the particle is formed from the luminescent polymer, and wherein the nucleic acid is attached to the luminescent polymer.

16. The polymeric article of claim 7, wherein the luminescent polymer comprises at least one pendant group.

17. The polymeric article of claim 16, wherein the pendant group comprises an aliphatic chain.

18. The polymeric article of claim 16, wherein the pendant group comprises an ether chain.

19. The polymeric article of claim 2, wherein the luminescent polymer comprises a charged moiety.

20. The polymeric article of claim 2, wherein the particle includes a coating.

22. An article, comprising:

a luminescent polymer particle comprising a nucleic acid wherein the luminescent polymer is a copolymer and comprises a triple bond.

26. A method, comprising:

allowing a nucleic acid to become covalently attached to a luminescent polymer, wherein the luminescent polymer comprises a triple bond.

27. The method of claim 26, wherein the luminescent polymer comprises a plurality of triple bonds.

28. The method of claim 26, wherein the luminescent polymer comprises a copolymer formed from a plurality of monomers, wherein at least one monomer comprises a structure:

29. An article, comprising:

a luminescent polymer particle comprising a nucleic acid, wherein the luminescent polymer comprises a triple bond, and wherein the particle luminesces when comprising the nucleic acid.

30. A polymeric article, comprising:

a particle consisting essentially of a luminescent polymer, wherein the luminescent polymer comprises a plurality of triple bonds.