IP Library Granted Patent US 9,908,901
Granted Patent B2
US 9,908,901 · App. 15/183,730 · Granted Mar 6, 2018

Articles and methods comprising persistent carbenes and related compositions

Inventors: Jeremiah A. Johnson (Boston, MA); Aleksandr V. Zhukhovitskiy (El Cerrito, CA)
Assignee: Massachusetts Institute of Technology
C07F7/0827C07F7/0814C07F7/0818
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Quick Facts
Patent No.
US 9,908,901
App. No.
15/183,730
Granted
Mar 6, 2018
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 (18)

1. A method, comprising:

associating a persistent carbene with a portion of a substrate,

wherein the persistent carbene is a cyclicaminocarbene or a diaminocarbene or other persistent carbene,

wherein the substrate comprises a silicon surface comprising a plurality of Si—H bonds, and wherein the association comprises insertion of the carbene into an Si—H bond.

2. The method of claim 1 , wherein the persistent carbene comprises the structure:

wherein R 5 is optionally substituted alkyl, optionally substituted heteroalkyl, optionally substituted aryl, or optionally substituted heteroalkyl; and each R 6 , R 7 , and R 8 is independently hydrogen, optionally substituted alkyl or optionally substituted heteroaryl, or optionally, two R 6 , two R 7 or two R 8 are joined together to form optionally substituted cycloalkylene or optionally substituted cycloheteroalkylene.

3. The method of claim 2 , wherein R 5 is optionally substituted aryl.

4. The method of claim 2 , wherein each R 6 is optionally substituted alkyl.

5. The method of claim 2 , wherein each R 7 is hydrogen.

6. The method of claim 2 , wherein the two R 8 are joined together to form an optionally substituted cycloalkylene.

7. The method of claim 1 , wherein the persistent carbene comprises the structure:

wherein each R 9 is the same or different and is optionally substituted alkyl, optionally substituted heteroalkyl, optionally substituted aryl, or optionally substituted heteroaryl.

8. The method of claim 7 , wherein each R 9 is optionally substituted alkyl.

9. The method of claim 1 , wherein the persistent carbene comprises the structure:

10. The method of claim 1 , wherein the substrate comprises a silicon wafer.

11. The method of claim 1 , wherein the substrate comprises a plurality of silicon nanoparticles.

12. An article formed using the method of claim 1 .

13. The article of claim 12 , wherein the article is a solar cell or a microelectronic device.

Assignments (2)
CONFIRMATORY LICENSE Recorded Jan 25, 2018
From: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 045153/0799 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2017
From: JOHNSON, JEREMIAH A.; ZHUKHOVITSKIY, ALEKSANDR V.
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 041371/0965 →
Continuity (7)
Continuation In Part 15171998 · Jun 2, 2016
Division 14210187 · Mar 13, 2014
Division 15183730
Continuation In Part 14210187 · Mar 13, 2014
Provisional Application 61817529 · Apr 30, 2013
Provisional Application 61779251 · Mar 13, 2013
Related Publication 20160289248A1 · Oct 6, 2016