IP Library Granted Patent US 9,382,210
Granted Patent B2
US 9,382,210 · App. 14/210,187 · Granted Jul 5, 2016

Articles and methods comprising persistent carbenes and related compositions

Inventors: Jeremiah A. Johnson (Boston, MA); Aleksandr V. Zhukhovitskiy (Cambridge, MA)
Assignee: Massachusetts Institute of Technology
C07D233/20C07D403/10C07D403/14
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Quick Facts
Patent No.
US 9,382,210
App. No.
14/210,187
Granted
Jul 5, 2016
Kind
B2
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.

Claims (19)

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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2014
From: JOHNSON, JEREMIAH A.; ZHUKHOVITSKIY, ALEKSANDR V.
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 033493/0728 →
Continuity (3)
Provisional Application 61817529 · Apr 30, 2013
Provisional Application 61779251 · Mar 13, 2013
Related Publication 20140275555A1 · Sep 18, 2014