Graphene nanoribbons with controlled zig-zag edge and cove edge configuration

Patent metadata

Field	Value
Publication number	US-10329378-B2
Application number	US-201515118796-A
Country	US
Kind code	B2
Filing date	Feb 9, 2015
Priority date	Feb 13, 2014
Publication date	Jun 25, 2019
Grant date	Jun 25, 2019

Abstract

Provided are graphene nanoribbons with controlled zig-zag edge and cove edge configuration and methods for preparing such graphene nanoribbons. The nanoribbons are selected from the following formulae.

First claim

The invention claimed is:

1. A graphene nanoribbon, represented by structure (i), structure (ii), structure (iii), structure (iv), structure (v), structure (vi), structure (vii), structure (viii), or structure (ix):

wherein:
X independently from each other, are a leaving group, hydrogen, or a free radical;
R b independently from each other are hydrogen, a linear C 1 -C 30 alkyl, a branched C 1 -C 30 , alkyl, OR 3 or NR 1 R 2 ;
wherein:
R 1 and R 2 are, independently of each other, hydrogen, a linear C 1 -C 6 alkyl, a 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 represented by

and
R 3 is selected from hydrogen, C 1 -C 30 alkyl and phenyl, which may be unsubstituted or substituted by one or more C 1 -C 4 alkyl, phenyl, halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkylthiol; or
R b is alpha-hydrogen substituted aryl that may form a 5-membered carbocyclic ring with a neighboring hydrogen substituted edge carbon by cycloannelation; or
one of two direct neighboring groups R b is an alpha-hydrogen substituted aryl and the other is hydrogen, and the two carbon atoms substituted with hydrogen may form a 5-membered carbocyclic ring by cycloannelation,
R c independently of each other, are hydrogen or C 1 -C 10 alkyl; or
two neighboring groups R c are hydrogen, and the two carbon atoms substituted with hydrogen may form a 5-membered carbocyclic ring by cycloannelation; and
n is an integer of from 2 to 2500.

2. The graphene nanoribbon according to claim 1 , represented by structure (i).

3. The graphene nanoribbon according to claim 1 , represented by structure (ii).

4. The graphene nanoribbon according to claim 1 , represented by structure (iii).

5. The graphene nanoribbon according to claim 1 , represented by structure (iv).

6. The graphene nanoribbon according to claim 1 , represented by structure (vi).

7. The graphene nanoribbon according to claim 1 , represented by structure (vii).

8. The graphene nanoribbon according to claim 1 , represented by structure (viii).

9. The graphene nanoribbon according to claim 1 , represented by structure (ix).

10. A process for preparing the graphene nanoribbon according to claim 1 , the process comprising:
(a) providing at least one aromatic monomer compound, which is at least one substituted or unsubstituted polycyclic aromatic monomer compound, at least one substituted or unsubstituted oligo phenylene aromatic monomer compound, or any combination thereof, on a solid substrate;
(b) polymerizing of the aromatic monomer compound so as to form at least one polymer on the surface of the solid substrate; and
(c) at least partially cyclodehydrogenating the one or more polymers of said (b) polymerization to obtain the graphene nanoribbon having structure (i), structure (ii), structure (iii), structure (iv), structure (v), structure (vi), structure (vii), structure (viii), or structure (ix).

11. A process for preparing the graphene nanoribbon according to claim 1 , the process comprising:
(a) providing at least one aromatic monomer compound which is at least one substituted or unsubstituted polycyclic aromatic monomer compound, at least one substituted or unsubstituted oligo phenylene aromatic monomer compound, or any combination thereof, in solution;
(b) polymerizing of the aromatic monomer compound so as to form at least one polymer; and
(c) at least partially cyclodehydrogenating the one or more polymers of said (b) polymerization to obtain the graphene nanoribbon having structure (i), structure (ii), structure (iii), structure (iv), structure (v), structure (vi), structure (vii), structure (viii), or structure (ix).

Assignees

• Basf Se
• Empa Eidgenoessische Mat & Forschungsanstalt
• Max Planck Gesellschaft

Inventors

• Schwab Matthias Georg
• Muellen Klaus
• Feng Xinliang
• Yang Bo
• Dumslaff Tim
• Fasel Roman
• Ruffieux Pascal
• Liu Jia
• Cai Jinming
• Sanchez-Sanchez Carlos
• Liu Junzhi

Classifications

• C08G2261/72

  Derivatisation · CPC title

• C08G2261/314

  Condensed aromatic systems, e.g. perylene, anthracene or pyrene · CPC title

• C08G61/10 Primary

  only aromatic carbon atoms, e.g. polyphenylenes · CPC title

• C07C25/22

  with condensed rings · CPC title

• C07C15/20

  Polycyclic condensed hydrocarbons · CPC title