Graphene nanoribbons with controlled modifications

Patent metadata

Field	Value
Publication number	US-9676755-B2
Application number	US-201314402560-A
Country	US
Kind code	B2
Filing date	May 13, 2013
Priority date	May 24, 2012
Publication date	Jun 13, 2017
Grant date	Jun 13, 2017

Abstract

The present invention relates to a graphene nanoribbon, comprising a repeating unit which comprises at least one modification, wherein the modification is selected from a heteroatomic substitution, a vacancy, a sp 3 hybridization, a Stone-Wales defect, an inverse Stone-Wales defect, a hexagonal sp 2 hybridized carbon network ring size modification, and any combination thereof.

First claim

The invention claimed is:

1. A graphene nanoribbon, comprising:
a repeating unit RU1 which comprises at least one modification,
wherein the modification is selected from the group consisting of a heteroatomic substitution, a vacancy, a sp a hybridization, a Stone-Wales defect, an inverse Stone-Wales defect, a hexagonal sp 2 hybridized carbon network ring size modification, and any combination thereof.

2. The graphene nanoribbon according to claim 1 , wherein the at least one heteroatomic substitution modification of the repeating unit RU1 comprises a heteroatom or a heteroatomic group selected from nitrogen, boron, phosphor and oxides thereof, silicon, oxygen, sulphur and oxides thereof, hydrogen, and any combination thereof.

3. The graphene nanoribbon according to claim 1 , wherein the repeating unit RU1 is derived from at least one aromatic monomer compound which is selected from the group consisting of at least one substituted or unsubstituted polycyclic aromatic monomer compound, at least one substituted or unsubstituted oligo phenylene aromatic monomer compound, and any combination thereof.

4. The graphene nanoribbon according to claim 3 , wherein the aromatic monomer compound comprises at least one aromatic or non-aromatic heterocyclic ring.

5. The graphene nanoribbon according to claim 3 , wherein the polycyclic aromatic monomer compound comprises two or more annelated aromatic rings and at least one of the annelated aromatic rings comprises one or more heteroatoms.

6. The graphene nanoribbon according to claim 3 , wherein the polycyclic aromatic monomer compound comprises two or more annelated aromatic rings and at least one non-annelated heterocyclic residue is attached to at least one of the annelated aromatic rings; and/or the oligo phenylene aromatic monomer compound comprises at least one heterocyclic residue being attached to the phenylene group.

7. The graphene nanoribbon according to claim 3 , wherein the aromatic monomer compound has one of the following formulas 2 to 4:

wherein:
X is each independently a leaving group;
Y is alkyl, aryl, or hydrogen; and
R is each independently selected from the group consisting of hydrogen; linear or branched or cyclic C 1 -C 12 alkyl which is unsubstituted or substituted by one or more OH, C 1 -C 4 alkoxy, phenyl, or CN; C 2 -C 12 alkyl which is interrupted by one or more non-consecutive O; halogen; OH; OR 3 ; SR 3 ; CN; NO 2 ; NR 1 R 2 ; (CO)R 3 ; (CO)OR 3 ; O(CO)OR 3 ; O(CO)NR 1 R 2 ; O(CO)R 3 ; C 1 -C 12 alkoxy; C 1 -C 12 alkylthio; (C 1 -C 6 alkyl)-NR 7 R 8 ; —O—(C 1 -C 6 alkyl)NR 1 R 2 ; aryl or heteroaryl which is unsubstituted or substituted by one or more C 1 -C 4 -alkyl, CN, OR 3 , SR 3 , CH 2 OR 3 , (CO)OR 3 , (CO)NR 1 R 2 or halogen); or two R's together with the carbon atoms they are attached to form a 5-8-membered cycle or heterocycle;
wherein:
R 1 and R 2 independently of each other are hydrogen, linear or branched C 1 -C 6 alkyl or phenyl, or R 1 and R 2 together with the nitrogen atom to which they are bonded form a group selected from the group consisting of

R 3 is selected from the group consisting of H, C 1 -C 12 alkyl, phenyl which is unsubstituted or is substituted by one or more C 1 -C 4 alkyl, phenyl, halogen, C 1 -C 4 alkoxy and C 1 -C 4 alkylthio.

8. The graphene nanoribbon according to claim 3 , wherein the aromatic monomer compound has the following formula 1:

wherein
X is each independently a leaving group.

9. The graphene nanoribbon according to claim 7 , wherein the graphene nanoribbon comprises one of the following structures:

wherein:
X, Y, and R are as defined in claim 7 , and
n≦2500.

10. A process for preparing the graphene nanoribbon according to claim 1 , which comprises:
(a) providing at least one aromatic monomer compound which is selected from the group consisting of at least one substituted or unsubstituted polycyclic aromatic monomer compound, at least one substituted or unsubstituted oligo phenylene aromatic monomer compound, and combinations thereof, on a solid substrate,
(b) polymerizing the aromatic monomer compound and forming at least one polymer on the surface of the solid substrate, and
(c) at least partially cyclodehydrogenating the at least one polymer of (b).

11. The process according to claim 10 , wherein the polymerizing in (b) is induced by thermal activation.

12. The process according to claim 10 , wherein the aromatic monomer compound is a polycyclic aromatic monomer compound and/or an oligo phenylene aromatic monomer compound.

Assignees

• Basf Se
• Empa—Eidgenoessische Materialpruefungs- Und Forschungsanstalt
• Max-Planck-Gesellschaft Zur Foerderung Der Wss E V
• Empa-Eidgenoessische Materialpruefungs-Und Forschungsanstalt
• Max-Planck-Gesellschaft Zur Foerderung Der Wss E V

Inventors

• Fasel Roman
• Ruffieux Pascal
• Muellen Klaus
• Cai Jinming
• Feng Xinliang
• Berger Reinhard

Classifications

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• B82Y30/00

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

• C07D215/18

  Halogen atoms or nitro radicals · CPC title

• C07D239/72

  Quinazolines; Hydrogenated quinazolines · CPC title

• C01B31/0438

  Chemistry & Metallurgy · mapped topic