Photochemical methods and photoactive compounds for modifying surfaces

• US 8,957,225 B2
• Filed: 03/09/2012
• Issued: 02/17/2015
• Est. Priority Date: 11/09/2005
• Status: Expired due to Fees

• Current Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Original Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Inventors: Carroll, Gregory T., Koberstein, Jeffrey T., Wang, Denong, Turro, Nicholas J.
• Primary Examiner(s): Jackson, Shawquia
• Application Number:
  US13/416,968
• Publication Number:
  US 20120178650A1
• Time in Patent Office: 1,075 Days
• Field of Search: 548/485
• US Class Current: 548/485
• CPC Class Codes: B05D 3/06 by exposure to radiation B05D3/02 takes precedence ; plasma treatment B05D3/141
• CPC Class Codes: B05D 3/067 Curing or cross-linking the coating
• CPC Class Codes: B05D 5/00 Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
• CPC Class Codes: B05D 7/02 to macromolecular substances, e.g. rubber treatment or coating of shaped articles made of macromolecular substances C08J7/00
• CPC Class Codes: B05D 7/14 to metal, e.g. car bodies involving a chemical reaction between the metal and the coating C23
• CPC Class Codes: C07C 49/303 to a six-membered ring
• CPC Class Codes: C07C 69/76 Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07D 209/48 with oxygen atoms in positions 1 and 3, e.g. phthalimide
• CPC Class Codes: C23C 18/1612 through irradiation means
• CPC Class Codes: C23C 18/1641 Organic substrates, e.g. resin, plastic
• CPC Class Codes: C23C 18/30 Activating or accelerating or sensitising with palladium or other noble metal
• CPC Class Codes: C23C 18/32 Coating with nickel, cobalt or mixtures thereof with phosphorus or boron C23C18/50 takes precedence
• CPC Class Codes: G03F 7/0045 with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
• CPC Class Codes: G03F 7/20 Exposure; Apparatus therefor photographic printing apparatus for making copies G03B27/00

Abstract

Compounds and methods for controlling the surface properties are described. Compounds of the invention can form radicals upon exposure to irradiation, which can then react with nearby molecules to alter the surface properties of various substrates. The invention can provide surfaces that are resistant to dewetting, surfaces that have immobilized molecules such as carbohydrates and polymers immobilized, and surfaces that have metals deposited on the surface. The invention can be utilized in a wide range of application, such as sensors, microreactors, microarrays, electroless deposition of metals, and the like.

Claims

1. A compound of the formula

2. An array comprising:

a surface;

a compound of formula (IV)

3. The array of claim 2, wherein n is from 1 to 20.

4. The array of claim 2, wherein the at least one molecule comprises at least one carbohydrate.

5. The array of claim 4, wherein the at least one carbohydrate comprises one or more of a monosaccharide, an oligosaccharide, or a polysaccharide.

6. The array of claim 2, wherein the at least one molecule comprises at least one DNA, at least one RNA, at least one peptide, or at least one protein.

7. The array of claim 2, wherein the at least one molecule comprises at least one polymer.

8. The array of claim 7, wherein the at least one polymer comprises a hydrophilic polymer, a hydrophobic polymer, or combinations thereof.

9. The array of claim 2, further comprising a second compound immobilized on at least a part of the surface, wherein the second compound is capable of improving an affinity of the at least one molecule to the compound of formula (IV).

10. The array of claim 2, wherein the second compound comprises an amine group.

11. The array of claim 10, wherein the compound of formula (IV) and the second compound are immobilized on at least a part of the surface as a self-assembled monolayer.

12. The array of claim 11, wherein a ratio of the compound of formula (IV) and the second compound is from about 1:

1 to about 1;

100.

13. The array of claim 12, wherein a ratio of the compound of formula (IV) and the second compound is from about 1:

5 to about 1;

20.