Small molecules based free-standing films and hybrid materials

Patent metadata

Field	Value
Publication number	US-11897884-B2
Application number	US-201816621278-A
Country	US
Kind code	B2
Filing date	Jun 13, 2018
Priority date	Jun 13, 2017
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

This invention is directed to an aromatic material based free-standing film, a hybrid of organic crystalline materials and inorganic carbon nanomaterials, process of preparation and uses thereof. The film, which comprises a fibrous organic nanocrystals of an aromatic material, is mechanically and thermally stable. This film is optionally reinforced by hybridization with a reinforcement material, such as carbon nanotube, carbon material, a polysaccharide, a nanoclay a metal, metal alloy, or an organic polymer. The hybrid film of organic nanocrystals and carbon nanotubes (ONC/CNT) has high conductivity and high thermal stability. The films or hybrids of this invention are used as microfiltration membranes for various materials, in electrodes or perovskite solar cells.

First claim

What is claimed is:

1. A hybrid composition comprising a carbon nanotube (CNT) and organic nanocrystals (ONC), wherein the organic nanocrystal comprises a perylene diimide derivative, represented by the structure of formula IA, B3, II or III:

wherein,
X is —NR 3 ;
Y is —NR 4 ;
R 1 is H, R 5 , (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 3 -C 8 )cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted; or R 1 is joined together with R 7 to form a substituted or unsubstituted five or six membered ring, or a substituted or unsubstituted five or six membered fused ring;
R 2 is H, R 5 , (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 3 -C 8 )cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted; or R 2 is joined together with R 8 to form a substituted or unsubstituted five or six membered ring, or a substituted or unsubstituted five or six membered fused ring;
R 3 and R 4 are each independently H, (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 3 -C 8 )cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted;
R 5 is OR 6 , OCH 3 , CF 3 , halide, COR 6 , COCl, COOCOR 6 , COOR 6 , OCOR 6 , OCONHR 6 , NHCOOR 6 , NHCONHR 6 , OCOOR 6 , CON(R 6 ) 2 , SR 6 , SO 2 R 6 , SO 2 M, SOR 6 , SO 3 H, SO 3 M, SO 2 NH 2 , SO 2 NH(R 6 ), SO 2 N(R 6 )2, NH 2 , NH(R 6 ), N(R 6 )2, CONH 2 , CONH(R 6 ), CON(R 6 )2, CO(N-heterocycle) NO 2 , OH, CN, cyanate, isocyanate, thiocyanate, isothiocyanate, mesylate, tosylate, triflate, PO(OH) 2 or OPO(OH) 2 ; wherein M is a monovalent cation;
R 6 is H, (C 1 -C 10 )haloalkyl, (C 3 -C 8 )cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted;
R 7 is H or is joined together with R 1 to form a substituted or unsubstituted five or six membered ring, or a substituted or unsubstituted five or six membered fused ring; and
R 8 is H or is joined together with R 2 to form a substituted or unsubstituted five or six membered ring, or a substituted or unsubstituted five or six membered fused ring.

2. The hybrid composition of claim 1 , further comprising an organic polymer.

3. The hybrid composition of claim 2 , wherein said organic polymer is selected from the group consisting of: polyvinyl alcohol, polyethylene glycol (PEG), polyethylene, polypropylene, polystyrene, polyacrylonitrile, polyamide, polyimide, polyester and any combination thereof.

4. The hybrid composition of claim 3 , wherein said organic polymer is polystyrene.

5. The hybrid composition according to claim 1 , wherein the carbon nanotubes are single walled carbon nanotubes (SWCNTs) or a multi walled carbon nanotubes (MWCNTs).

6. The hybrid composition of claim 1 , wherein the composition comprises one or more different perylene diimides derivatives.

7. The hybrid composition of claim 1 , wherein the perylene diimide derivative is represented by the structure of formula 1-3, 4a, 4b or 5:

8. The hybrid composition of claim 7 wherein the perylenediimide derivative is a mixture of 4a and 4b.

9. The hybrid composition according to claim 1 , wherein the composition comprises between 3 wt % to 85 wt % of CNT.

10. An electrode comprising a hybrid composition according to claim 1 .

11. The electrode of claim 10 , wherein said electrode is a cathode or an anode.

12. The electrode of claim 10 , further comprising a binder, an additive, a current collector or any combination thereof.

13. The electrode of claim 10 , wherein said hybrid composition is used as a binder, an additive, a current collector or any combination thereof.

14. A process for the preparation of the hybrid composition of claim 1 , the process comprises:
mixing a hydrophobic organic compound and a carbon nanotube (CNT) in a first organic solvent;
optionally drying the mixture;
adding to the mixture a second organic solvent and water to obtain an aqueous medium and mixing for a period of time to obtain the hybrid; wherein if the first organic solvent and the second organic solvent are the same, only water is added to the mixture.

15. A process for the preparation of the hybrid composition of claim 1 , the process comprises:
mixing a hydrophobic organic compound and a carbon nanotube (CNT) in a first organic solvent;
optionally drying the mixture;
optionally, adding to the mixture a second organic solvent to obtain an organic medium and mixing for a period of time to obtain the hybrid.

16. The process of claim 14 , wherein the hybrid is further purified by centrifugation, or precipitation to yield a homogenous dispersion of ONC/CNT hybrid composition.

17. The process of claim 15 , wherein the hybrid is further purified by centrifugation, or precipitation to yield a homogenous dispersion of ONC/CNT hybrid composition.

18. The process according to claim 14 , wherein the CNT is (6,5)-SWCNT, (7,6)-SWCNT, MWCNT or combination thereof.

19. The process according to claim 15 , wherein the CNT is (6,5)-SWCNT, (7,6)-SWCNT, MWCNT or combination thereof.

20. The process according to claim 14 , wherein the hydrophobic organic compound is perylenediimide (PDI) derivative, represented by the structure of formula IA, IB II or III:

wherein,
X is —NR 3 ;
Y is —NR 4 ;
R 1 is H, R 5 , (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 3 -C 8 )cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted; or R 1 is joined together with R 7 to form a substituted or unsubstituted five or six membered ring, or a substituted or unsubstituted five or six membered fused ring;
R 2 is H, R 5 , (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 3 -C 8 )cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted; or R 2 is joined together with R 8 to form a substituted or unsubstituted five or six membered ring, or a substituted or unsubstituted five or six membered fused ring;
R 3 and R 4 are each independently H, (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 3 -C 8 )cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted;
R 5 is OR 6 , OCH 3 , CF 3 , halide, CORE, COCl, COOCOR 6 , COOR 6 , OCOR 6 , OCONHR 6 , NHCOOR 6 , NHCONHR 6 , OCOOR 6 , CON(R 6 )2, SR 6 , SO 2 R 6 , SO 2 M, SOR 6 , SO 3 H, SO 3 M, SO 2 NH 2 , SO 2 NH(R 6 ), SO 2 N(R 6 ) 2 , NH 2 , NH(R 6 ), N(R 6 ) 2 , CONH 2 , CONH(R 6 ), CON(R 6 ) 2 , CO(N-heterocycle), NO 2 , OH, CN, cyanate, isocyanate, thiocyanate, isothiocyanate, mesylate, tosylate, triflate, PO(OH) 2 or OPO(OH) 2 ; wherein M is a monovalent cation;
R 6 is H, (C 1 -C 10 )haloalkyl, (C 3 -C 8 )cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted;
R 7 is H or is joined toget

Assignees

• Yeda Res & Dev

Inventors

• Rybtchinski Boris
• Weissman Haim
• Wolf Tamar
• ELKAN Angelica
• Dutta Sounak
• Bhaskar Kanth Siram Raja

Classifications

• H10K30/10

  comprising heterojunctions between organic semiconductors and inorganic semiconductors · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• C07D471/22 Primary

  in which the condensed systems contains four or more hetero rings · CPC title

• C09B5/62 Primary

  Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series · CPC title

• B01D2325/0283

  Pore size · CPC title