Articles and methods comprising persistent carbenes and related compositions

Patent metadata

Field	Value
Publication number	US-9382210-B2
Application number	US-201414210187-A
Country	US
Kind code	B2
Filing date	Mar 13, 2014
Priority date	Mar 13, 2013
Publication date	Jul 5, 2016
Grant date	Jul 5, 2016

Abstract

Articles and methods comprising persistent carbenes are provided, as well as related compositions. In some embodiments, a persistent carbene may be associated with a portion of a substrate (e.g., at least a portion of a surface on the substrate). In certain embodiments, the association of persistent carbene with the substrate may be used to affect certain properties of substrate (e.g., surface chemistry, stability). In some cases, a persistent carbene may be functionalized after association with a portion of a substrate. In some embodiments, a persistent carbene and at least one secondary compound may be associated with a portion of a substrate. Articles and methods of the present invention may be useful for applications involving electronics, sensing, microfabrication, nanotechnology, biomimetic, and drug delivery, amongst others.

First claim

What is claimed is:

1. A method, comprising:
associating a persistent carbene with a portion of a substrate, wherein the persistent carbene comprises at least one functionalizable group; and
functionalizing the at least one functionalizable group of the persistent carbene associated with the substrate.

2. The method of claim 1 , further comprising associating a secondary compound with a portion of the substrate.

3. The method of claim 2 , wherein the secondary compound comprises a thiol, thioether, selenol, dithiocarbamate, dithioate, dithiophosphinate, phosphonate, carboxylic acid and carboxylate group, amino, aminoacyl, pyridine, phosphine, alcohol, alkoxy, nitrile, isocyanide, alkyl, alkenyl, aryl, or alkynyl group.

4. The method of claim 2 , further comprising functionalizing the secondary compound.

5. The method of claim 1 , wherein a plurality of persistent carbenes are and/or a plurality of secondary compounds are associated with a portion of the substrate.

6. The method of claim 1 , wherein a portion of the plurality of persistent carbenes and/or a portion of the plurality of secondary compounds are functionalized.

7. The method of claim 6 , wherein the functionalizing comprises reacting the at least one functionalizable group of the persistent carbene via a chemical reaction with a compound comprising a functional group.

8. The method of claim 7 , wherein the chemical reaction is a cross-coupling reaction.

9. The method of claim 7 , wherein the chemical reaction is a polymerization reaction.

10. The method of claim 7 , wherein the chemical reaction is a click chemistry reaction.

11. The method of claim 7 , wherein the chemical reaction is not a click chemistry reaction.

12. The method of claim 7 , wherein the chemical reaction is an addition reaction.

13. The method of claim 7 , wherein the chemical reaction is an cycloaddition reaction.

14. The method of claim 7 , wherein the chemical reaction is an oxidation reaction.

15. The method of claim 7 , wherein the chemical reaction is a reduction reaction.

16. The method of claim 7 , wherein the chemical reaction is olefin metathesis.

17. The method of claim 7 , wherein the chemical reaction is an elimination reaction.

Assignees

• Massachusetts Inst Technology

Inventors

• Johnson Jeremiah A
• Zhukhovitskiy Aleksandr V

Classifications

• C07D233/06

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title

• C08F292/00

  Macromolecular compounds obtained by polymerising monomers on to inorganic materials · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D233/20 Primary

  with substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title