Attachment chemistry for organic molecules to silicon

• US 6,403,382 B1
• Filed: 12/08/1999
• Issued: 06/11/2002
• Est. Priority Date: 12/08/1998
• Status: Expired due to Term

• Current Assignee: Regents of The University of Minnesota (University of Minnesota)
• Original Assignee: Regents of The University of Minnesota (University of Minnesota)
• Inventors: Zhu, Xiaoyang, Yang, Hongjun
• Primary Examiner(s): Beck, Shrive P.
• Assistant Examiner(s): CLEVELAND, MICHAEL B
• Application Number:
  US09/456,556
• Time in Patent Office: 916 Days
• Field of Search: 427/212, 427/414, 435/174, 435/176, 436/86, 436/176
• US Class Current: 436/176
• CPC Class Codes: B05D 1/185 applying monomolecular layers B05D1/204 takes precedence
• CPC Class Codes: B05D 1/60 Deposition of organic layers from vapour phase vapour phase deposition in general C23C14/00, C23C16/00
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: B82Y 40/00 Manufacture or treatment of nanostructures
• CPC Class Codes: C07B 61/00 Other general methods
• CPC Class Codes: G01N 33/552 Glass or silica
• CPC Class Codes: Y10T 436/2525 Stabilizing or preserving

Abstract

A simple chemical approach for the covalent assembly of organic molecules on silicon surfaces via robust linkages is provided. This is achieved by the efficient reaction between a nucleophilic functional group and a halogenated Si surface. The nucleophile anchor is the bridge between two surface Si atoms. The resulting organic layer is thermally stable. The method demonstrated herein is generally applicable for the assembly of a variety of functional organic molecules under vacuum environment or in solution phase.

Claims

1. A method for attaching organic molecules to a silicon surface comprising reacting a nucleophilic organic molecule with a halogenated silicon surface, wherein said nucleophilic organic molecule contains a nucleophilic functionality selected from the group consisting of amines, ═

NH, —

OH, —

SH, —

SeH, —

TeH, and —

PH₂.

2. A method according to claim 1, wherein said silicon surface comprises a silicon selected from the group consisting of crystalline silicon, amorphous silicon, flat silicon, and porous silicon.

3. A method according to claim 1, wherein the reaction of said nucleophilic organic compound with said halogenated silicon surface is performed in solution phase or gas phase.

4. A method according to claim 1, wherein said halogenated silicon surface is prepared by reacting a silicon surface with a halogen source to form a halogenated silicon surface.

5. A method according to claim 4, wherein said silicon surface is prepared by heating a silicon surface to a temperature sufficient to remove impurities from the silicon surface.

6. A method according to claim 4, wherein said halogen source is a chlorine source and said halogenated silicon surface is a chlorinated silicon surface.

7. A method according to claim 6 wherein said chlorine source is selected from the group consisting of Cl₂, SO₂Cl₂, phosgene and oxalyl chloride.

8. A method according to claim 1, wherein said halogenated silicon surface is prepared by reacting a hydrogen terminated silicon surface with a halogen source in gas phase or in solution to form a halogenated silicon surface.

9. A method according to claim 8 wherein said halogen source is a chlorine source and said halogenated silicon surface is a chlorinated silicon surface.

10. A method according to claim 9 wherein said chlorine source is selected from the group consisting of Cl₂, SO₂Cl₂, Cl₃CSO₂Cl, n-chlorosuccinimide, C₆H₅Cl₂, t-C₄H₉OCl, PCl₅, phosgene and oxalyl chloride.

11. A method according to claim 8 wherein said silicon is reacted with said halogen source in the presence of a radical initiator catalyst, and said reaction is carried out in solution.

12. A method according to claim 11, wherein said catalyst is selected from the group consisting of azocompounds, peroxides, photons, and Bu₃SnH.

13. A method according to claim 12, wherein said catalyst is benzoyl peroxide.

14. A method of producing an improved device for detecting multiple binding reactions, comprising reacting an organic molecule containing a nucleophilic functionality with a halogenated silicon surface of said device, wherein said organic molecule is a bifunctional molecule having at least a first functional group and a second functional group, and wherein said first functional group is selected from the group consisting of amines, ═

NH, —

OH, —

SH, —

SeH, —

TeH, and —

PH₂.

15. The method according to claim 14 wherein said first and second functional groups are selected from —

OH and —

SH.

16. The method according to claim 14 further comprising linking said bifunctional molecule to a binding reagent selected from the group consisting of DNA, proteins, ligands, and oligonucleotide probes.

17. The method according to claim 16 wherein said bifunctional molecule is linked directly to said binding reagent.

18. The method according to claim 16, wherein said bifunctional molecule is linked to said binding reagent via a second bifunctional spacer molecule.

19. The method according to claim 16 wherein the binding reagents are oligonucleotide probes.

20. The method according to claim 16 wherein the binding reagents are attached within channels in a solid substrate.