Functionalized nanostructures and related devices

Patent metadata

Field	Value
Publication number	US-9755150-B2
Application number	US-201313785476-A
Country	US
Kind code	B2
Filing date	Mar 5, 2013
Priority date	Oct 17, 2012
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

Embodiments described herein provide functionalized carbon nanostructures for use in various devices, including photovoltaic devices (e.g., solar cells). In some embodiments, carbon nanostructures substituted with at least one cyclobutyl and/or cyclobutenyl group are provided. Devices including such materials may exhibit increased efficiency, increased open circuit potential, high electron/hole mobility, and/or low electrical resistance.

First claim

What is claimed:

1. A device, comprising:
a composition comprising a carbon nanostructure comprising at least one cyclobutyl and/or at least one cyclobutenyl group, any of which is optionally substituted; and
at least one electrode in electrochemical communication with the composition,
wherein the composition exhibits an increase in LUMO energy level of about 50 meV relative to the LUMO energy level of ([6,6]-phenyl-C61-butyric acid methyl ester) (PCBM).

2. A device as in claim 1 , wherein the carbon nanostructure comprises a fused network of aromatic rings, optionally comprising a border at which the fused network terminates, wherein the at least one cyclobutyl and/or at least one cyclobutenyl group is attached to the network via at least one ring atom of the network.

3. A device as in claim 2 , wherein two ring atoms of the at least one cyclobutyl and/or at least one cyclobutenyl group form covalent bonds with two ring atoms of the network of aromatic rings.

4. A device as in claim 1 , wherein the carbon nanostructure comprises two cyclobutenyl groups, optionally substituted.

5. A device as in claim 1 , wherein the carbon nanostructure comprises three cyclobutenyl groups, optionally substituted.

6. A device as in claim 1 , wherein the carbon nanostructure is a fullerene, a nanotube, graphene, or graphite.

7. A device as in claim 1 , wherein the carbon nanostructure comprises the following structure,

wherein:
A is a carbon nanostructure; and
R 1 -R 4 can be the same or different and hydrogen, hydroxyl, halo, alkyl, heteroalkyl, alkenyl, heteroalkenyl, aryl, heteroaryl, or heterocycle, any of which is optionally substituted.

8. A device as in claim 7 , wherein R 1 -R 4 are alkyl.

9. A device as in claim 1 , wherein the carbon nanostructure comprises the following structure,

wherein:
A is a carbon nanostructure; and
R 1 -R 6 can be the same or different and are hydrogen, hydroxyl, halo, alkyl, heteroalkyl, alkenyl, heteroalkenyl, aryl, heteroaryl, or heterocycle, any of which is optionally substituted, or any two of R 1 -R 6 are joined to form an optionally substituted ring.

10. A device as in claim 9 , wherein R 5 and R 6 are joined to form an epoxide ring.

11. A device as in claim 9 , wherein at least one of R 1 -R 4 is not hydrogen.

12. A device as in claim 9 , wherein at least one of R 1 -R 6 is not hydrogen.

13. A device as in claim 1 , wherein the device is a battery, capacitor, transistor, catalyst system, solar cell, or chemical or biological sensor.

14. A photovoltaic device, comprising:
a photoactive material comprising an electron donor material and an electron acceptor material comprising a carbon nanostructure and a cyclobutyl-containing group and/or a cyclobutenyl-containing group in contact with the electron donor material; and
at least two electrodes in electrical communication with the photoactive material,
the electron acceptor material exhibits an increase in LUMO energy level of about 50 meV relative to the LUMO energy level of ([6,6]-phenyl-C61-butyric acid methyl ester) (PCBM).

15. A photovoltaic device as in claim 14 , wherein electron acceptor material comprises a carbon nanostructure comprising the cyclobutyl-containing group and/or a cyclobutenyl-containing group, and wherein the carbon nanostructure comprises a fused network of aromatic rings, optionally comprising a border at which the fused network terminates, wherein the cyclobutyl and/or cyclobutenyl group is attached to the network via at least one ring atom of the network.

16. A photovoltaic device as in claim 15 , wherein the carbon nanostructure is a fullerene, a nanotube, graphene, or graphite.

17. A photovoltaic device as in claim 15 , wherein the carbon nano structure comprises the following structure,

wherein:
A is a carbon nanostructure; and
R 1 -R 4 can be the same or different and hydrogen, hydroxyl, halo, alkyl, heteroalkyl, alkenyl, heteroalkenyl, aryl, heteroaryl, or heterocycle, any of which is optionally substituted.

18. A photovoltaic device as in claim 17 , wherein R 1 -R 4 are alkyl.

19. A photovoltaic device as in claim 15 , wherein the carbon nano structure comprises the following structure,

wherein:
A is a carbon nanostructure; and
R 1 -R 6 can be the same or different and are hydrogen, hydroxyl, halo, alkyl, heteroalkyl, alkenyl, heteroalkenyl, aryl, heteroaryl, or heterocycle, any of which is optionally substituted, or any two of R 1 -R 6 are joined to form an optionally substituted ring.

20. A photovoltaic device as in claim 19 , wherein R 5 and R 6 are joined to form an epoxide ring.

21. A photovoltaic device as in claim 14 , wherein the electron donor material comprises a conducting polymer.

22. A photovoltaic device as in claim 14 , wherein the photovoltaic device is a solar cell.

Assignees

• Massachusetts Inst Technology
• Massachussets Inst Of Tech

Inventors

• Swager Timothy M
• Bulovic Vladimir
• Han Ggoch Ddeul
• Andrew Trisha L

Classifications

• Y10S977/948

  Energy storage/generating using nanostructure, e.g. fuel cell, battery · CPC title

• Y10S977/746

  Modified with biological, organic, or hydrocarbon material · CPC title

• Y10S977/738

  Modified with biological, organic, or hydrocarbon material · CPC title

• B82Y30/00

  Nanotechnology for materials or surface science, e.g. nanocomposites · CPC title

• Y02E10/549

  Organic PV cells · CPC title