Vol 466 | 22 July 2010 | doi:10.

1038/nature09211

LETTERS
Atomically precise bottom-up fabrication of graphene
nanoribbons
Jinming Cai1*, Pascal Ruffieux1*, Rached Jaafar1, Marco Bieri1, Thomas Braun1, Stephan Blankenburg1,
Matthias Muoth2, Ari P. Seitsonen3,4, Moussa Saleh5, Xinliang Feng5, Klaus Müllen5 & Roman Fasel1,6

Graphene nanoribbons—narrow and straight-edged stripes of temperature the dehalogenated intermediates have enough thermal
graphene, or single-layer graphite—are predicted to exhibit elec- energy to diffuse along the surface and form single covalent C–C
tronic properties that make them attractive for the fabrication of bonds between each monomer to give polymer chains. Scanning
nanoscale electronic devices1–3. In particular, although the two- tunnelling microscopy (STM) images of the colligated monomers
dimensional parent material graphene4,5 exhibits semimetallic show protrusions that appear alternately on both sides of the chain
behaviour, quantum confinement and edge effects2,6 should render axis and with a periodicity of 0.86 nm (Fig. 2b), in excellent agree-
all graphene nanoribbons with widths smaller than 10 nm semi- ment with the periodicity of the bianthryl core of 0.85 nm. Steric
conducting. But exploring the potential of graphene nanoribbons hindrance between the hydrogen atoms of adjacent anthracene units
is hampered by their limited availability: although they have rotates the latter around the s-bonds connecting them, resulting in
been made using chemical7–9, sonochemical10 and lithographic11,12 opposite tilts of successive anthracene units with respect to the metal
methods as well as through the unzipping of carbon nanotubes13–16, surface. This deviation from planarity explains the large apparent
the reliable production of graphene nanoribbons smaller than height of the polyanthrylenes of about 0.4 nm (Fig. 2b), with the
10 nm with chemical precision remains a significant challenge. finite size of the scanning probe tip moreover imaging the polymer
Here we report a simple method for the production of atomically with a width much larger (1.5 nm) than expected from the structural
precise graphene nanoribbons of different topologies and widths,
which uses surface-assisted coupling17,18 of molecular precursors Precursor monomer ‘Biradical’ intermediate
into linear polyphenylenes and their subsequent cyclodehydro-
genation19,20. The topology, width and edge periphery of the gra-
phene nanoribbon products are defined by the structure of the Br Br
precursor monomers, which can be designed to give access to a
wide range of different graphene nanoribbons. We expect that 1
our bottom-up approach to the atomically precise fabrication of Dehalogenation C–C coupling
graphene nanoribbons will finally enable detailed experimental
investigations of the properties of this exciting class of materials. Linear polymer
It should even provide a route to graphene nanoribbon structures
with engineered chemical and electronic properties, including the
theoretically predicted intraribbon quantum dots21, superlattice
structures22 and magnetic devices based on specific graphene
nanoribbon edge states3.
Figure 1 sketches the basic graphene nanoribbon (GNR) fabrica- Cyclodehydrogenation
tion steps for the prototypical armchair ribbon6 of width N 5 7
obtained from 10,109-dibromo-9,99-bianthryl precursor monomers. Graphene nanoribbon
Thermal sublimation of the monomers onto a solid surface removes
their halogen substituents, yielding the molecular building blocks of
the targeted graphene ribbon in the form of surface-stabilized bira-
dical species. During a first thermal activation step, the biradical
species diffuse across the surface and undergo radical addition reac-
tions17 to form linear polymer chains as imprinted by the specific
chemical functionality pattern of the monomers. In a second thermal Figure 1 | Bottom-up fabrication of atomically precise GNRs. Basic steps for
activation step a surface-assisted cyclodehydrogenation establishes surface-supported GNR synthesis, illustrated with a ball-and-stick model of
the example of 10,109-dibromo-9,99-bianthryl monomers (1). Grey, carbon;
an extended fully aromatic system. white, hydrogen; red, halogens; underlying surface atoms shown by large
Figure 2 shows GNRs obtained according to the scheme in Fig. 1, spheres. Top, dehalogenation during adsorption of the di-halogen
using precursor monomers 1 and a Au(111) surface. The first step functionalized precursor monomers. Middle, formation of linear polymers
to GNR fabrication—intermolecular colligation through radical by covalent interlinking of the dehalogenated intermediates. Bottom,
addition—is thermally activated by annealing at 200 uC, at which formation of fully aromatic GNRs by cyclodehydrogenation.
1
Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 3602 Thun and 8600 Dübendorf, Switzerland. 2ETH Zurich, Department of
Mechanical and Process Engineering, Micro and Nanosystems, 8092 Zurich, Switzerland. 3University of Zurich, Physical Chemistry Institute, Winterthurerstrasse 190, 8057 Zurich,
Switzerland. 4IMPMC, CNRS and Université Pierre et Marie Curie, 4 place Jussieu, case 115, F-75252 Paris, France. 5Max Planck Institute for Polymer Research, Ackermannweg 10,
55124 Mainz, Germany. 6Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
*These authors contributed equally to this work.

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©2010 Macmillan Publishers Limited. All rights reserved
NATURE | Vol 466 | 22 July 2010 LETTERS

a d a c
Br
1,600 Br Br
200 ºC 400 ºC 80

Number
60
1,341
1,260 2 40
Br
1 396
20
250 ºC 0
1,220 440 ºC 0 20 40 60
b 953
Length (nm)
Experiment

Calculation
400 600 800 1,000 1,200 1,400 1,600
0 3.8 Å 1 nm
Wavenumber (cm–1) b
c 0 2Å e
20 nm

d XPS
hν = 1486.7 eV

C 1s Au 4f
Au 4d
288 286 284 282
Au 5p
Au 4s Au 4p
0 1.8 Å Au 5s
C 1s VB

1 nm 15 nm 700 600 500 400 300 200 100 0

Binding energy (eV)
20 nm 3 nm 1 nm
Figure 3 | Chevron-type GNRs from tetraphenyl-triphenylene monomers.
a, Reaction scheme from 6,11-dibromo-1,2,3,4-tetraphenyltriphenylene
Figure 2 | Straight GNRs from bianthryl monomers. a, Reaction scheme monomer 2 to chevron-type GNRs. b, Overview STM image of chevron-type
from precursor 1 to straight N 5 7 GNRs. b, STM image taken after surface- GNRs fabricated on a Au(111) surface (T 5 35 K, U 5 22 V, I 5 0.02 nA).
assisted C–C coupling at 200 uC but before the final cyclodehydrogenation The inset shows a high-resolution STM image (T 5 77 K, U 5 22 V,
step, showing a polyanthrylene chain (left, temperature T 5 5 K, voltage I 5 0.5 nA) and a DFT-based simulation of the STM image (greyscale) with
U 5 1.9 V, current I 5 0.08 nA), and DFT-based simulation of the STM partly overlaid molecular model of the ribbon (blue, carbon; white,
image (right) with partially overlaid model of the polymer (blue, carbon; hydrogen). c, Monolayer sample of chevron GNRs on Au(111): STM image
white, hydrogen). c, Overview STM image after cyclodehydrogenation at and corresponding ribbon length distribution. d, XPS survey of a monolayer
400 uC, showing straight N 5 7 GNRs (T 5 300 K, U 5 23 V, I 5 0.03 nA). sample of chevron-type GNRs with core levels and valence band (VB)
The inset shows a higher-resolution STM image taken at 35 K (U 5 21.5 V, labelled. The C1s core level spectrum (inset) consists of a single component
I 5 0.5 nA). d, Raman spectrum (532 nm) of straight N 5 7 GNRs. The peak located at 284.5 eV binding energy (full-width at half-maximum, FWHM
at 396 cm21 is characteristic for the 0.74 nm width of the N 5 7 ribbons. The 0.87 eV). The absence of oxygen-related spectral features proves the
inset shows the atomic displacements characteristic for the radial-breathing- chemical inertness of the GNRs with respect to ambient conditions: blue bars
like mode at 396 cm21. e, High-resolution STM image with partly overlaid indicate the energy position for C–O, C 5 O and COOH (with increasing
molecular model (blue) of the ribbon (T 5 5 K, U 5 20.1 V, I 5 0.2 nA). At chemical shift); see text.
the bottom left is a DFT-based STM simulation of the N 5 7 ribbon shown as
a greyscale image.
to the polymer main axis (Supplementary Fig. 2). The fully aromatic
model (1.0 nm). STM simulations (Fig. 2b, right side, greyscale) that GNR is then produced during a second annealing step at 440 uC,
account for the finite tip radius perfectly reproduce the apparent which causes intramolecular cyclodehydrogenation of the polymer
height and width of the polyanthrylenes. The fully aromatic system chain as is shown by a reduction of the apparent height from 0.25 nm
is obtained by annealing the sample in a second step at 400 uC, which to 0.18 nm (Supplementary Fig. 3). The resultant chevron-type GNRs
induces intramolecular cyclodehydrogenation of the polymer chain have a periodicity of 1.70 nm and a pure armchair edge structure
and hence the formation of an N 5 7 armchair ribbon (Fig. 2c) with (Fig. 3b, c). Comparisons with the model structure and with density
half the periodicity of the polymeric chain (0.42 nm) and a markedly function theory (DFT) -based STM simulations (Fig. 3b) confirm
reduced apparent height of 0.18 nm (Supplementary Fig. 3). STM that the structure of the chevron-type ribbon has been imposed by
simulations are in perfect agreement with experimental images the colligated and cyclodehydrogenated monomer 2.
(Fig. 2e), confirming that the reaction products are atomically precise Figure 3c shows a monolayer thin film of N 5 6/N 5 9 chevron-
N 5 7 GNRs with fully hydrogen-terminated armchair edges. type armchair GNRs, with the degree of alignment between neigh-
The Raman spectrum in Fig. 2d of a densely packed layer of N 5 7 bouring GNRs improved over that seen in low-coverage samples. The
armchair GNRs grown on a 200-nm Au(111) film on a mica substrate preferred growth direction of the GNRs is given by the herringbone
further attests to the uniform width of the ribbons: besides the D and G reconstruction of the Au(111) substrate. The substrate-controlled
peaks23 and several other peaks appearing due to the finite width and growth direction also limits the ribbon length: The length histogram
low symmetry of the ribbons, the spectrum exhibits the width-specific (inset in Fig. 3c) drops significantly above ,30 nm, which corre-
radial-breathing-like mode24 as a sharp peak at 396 cm21 (in excellent sponds to the typical length of the straight segments of the herring-
agreement with our calculated value of 394 cm21). This implies that bone reconstruction of the Au(111) sample used. A significant
the radial-breathing-like mode is indeed a sensitive probe of GNR increase in ribbon length can thus be expected for template surfaces
width (N 5 6 and N 5 8 GNRs have radial-breathing-like mode fre- favouring unidirectional ribbon growth25,26.
quencies about 50 cm21 higher and lower, respectively24). An X-ray photoelectron spectroscopy (XPS) analysis of a mono-
In our method the topology of the GNRs produced is determined layer thin film of N 5 6/N 5 9 chevron-type armchair GNRs grown
by the functionality pattern of the precursor monomers, allowing the on a Au(111)/mica surface was performed after sample transfer
fabrication of ribbons with complex shapes. As an example, Fig. 3a through air and subsequent annealing to 450 uC under ultrahigh-
illustrates the strategy for fabricating chevron-type GNRs with vacuum conditions to desorb volatile contaminants accumulated
alternating widths of N 5 6 and N 5 9 using 6,11-dibromo-1,2,3,4- during air exposure. The overview XPS spectrum shown in Fig. 3d
tetraphenyltriphenylene precursor monomers 2. Initial colligation of exhibits only core level peaks owing to the gold substrate and the
the dehalogenated intermediates on Au(111) at 250 uC yields chains, GNRs. The enlarged view of the C1s core level region in the inset
in which adjacent monomers have opposite orientation with respect shows that the C 1s peak consists of a single sharp component at
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©2010 Macmillan Publishers Limited. All rights reserved
LETTERS NATURE | Vol 466 | 22 July 2010

284.5 eV binding energy characteristic of sp2 bonded carbon. There fabrication even holds promise for the growth of chemically doped
are no signs of carbon in other chemical environments, and in par- GNRs from precursor monomers with phenyl rings substituted by
ticular no C–O, C5O or COOH components27. We conclude that the heterocycles (with heteroatoms at positions that do not interfere with
GNRs are chemically pure, and inert under ambient conditions. XPS cyclodehydrogenation), leading to isostructural GNRs but with
also shows that the halogens desorb from the surface before the final heteroatoms at strictly defined positions along the ribbon edges.
cyclodehydrogenation step. The present bottom-up route to atomically precise GNRs involves
Suitably designed halogen-functionalized molecular precursors will modest temperatures (,450 uC) compatible with current comple-
provide access to a wide range of other GNR shapes and widths and mentary metal–oxide–semiconductor (CMOS) technology, and all
thus enable the engineering of electronic properties. For example, the fabrication steps are performed in situ so that the intrinsic properties
N 5 7 armchair GNR obtained from precursor 1 (Fig. 2) exhibits a of the GNRs can be probed on clean and well-defined substrates.
bandgap of 1.6 eV (Supplementary Fig. 4), whereas the related N 5 9 However, the technological use of this fabrication method faces some
and N 5 11 ribbons are predicted to exhibit much smaller bandgaps of challenges, such as its extension to substrates that are technologically
about 0.7 eV and 0.2 eV, respectively (Supplementary Fig. 6)2,6,28. The relevant while still being able to induce the dehalogenation, C–C
chevron-like GNR consisting of alternating N 5 6 and N 5 9 segments coupling and cyclodehydrogenation steps. An alternative might be
(Fig. 3) exhibits the same bandgap of 1.6 eV (Supplementary Fig. 4) offered by the adaptation of transfer methods developed for epitaxial
despite its different topology. However, its conduction bands are graphene29,30, with preliminary results using a simple ‘chip-to-chip
much less strongly dispersing, indicating a significant degree of charge press’ method indicating that intact GNRs can be successfully trans-
carrier localization owing to the peculiar ‘zigzag’ shape of the ribbon ferred from gold films onto a SiO2 substrate (Supplementary Fig. 7).
(Supplementary Fig. 5). This suggests that the rational design of GNR
width and shape (topology) allows not only for a detailed engineering METHODS SUMMARY
of the bandgap, but also of the band curvature and thus the effective Preparation of GNRs. Au(111) and Ag(111) single crystals (Surface Preparation
Laboratory, Netherlands) as well as 200 nm Au(111) thin films epitaxially grown on
mass (mobility) of charge carriers.
mica (Phasis, Switzerland) were used as substrates for GNR growth. Substrate
Our bottom-up GNR fabrication process is not limited to Au(111) surfaces were cleaned by repeated cycles of argon ion bombardment and annealing
templates, with Ag(111) equally suitable for the fabrication of the two to 470 uC. Precursor monomers (for details on the synthesis, see the Supplementary
types of GNRs discussed above. This is illustrated by the sample in Information) were deposited onto the clean substrate surfaces by sublimation from
Fig. 4a, with the straight N 5 7 GNRs and the chevron-type a sixfold evaporator (Knudsen-cell type) at rates of ,1 Å min21. Owing to a large
N 5 6/N 5 9 GNRs having been grown sequentially on a Ag(111) distance between substrate and evaporator in our ultrahigh-vacuum set-up, only
surface. Incidentally, a sample containing both GNRs is also obtained ,2% of the sublimated material reaches the sample. For the fabrication of straight
if both precursor monomers are deposited together on the substrate N 5 7 armchair GNRs, the substrate was maintained at 200 uC during monomer
deposition to induce dehalogenation and radical addition. After deposition, the
surface and the thermal activation sequence is then applied to the
sample was post-annealed at 400 uC for 10 min to cyclodehydrogenate the poly-
mixed sample. The intermolecular coupling reaction is thus highly mers and form GNRs. For the chevron-type GNRs, the preparation process was
selective: the design of the two monomers allows only homomolecular identical, except that slightly higher substrate temperatures of 250 uC and 440 uC
reactions, whereas heteromolecular coupling is sterically hindered. were used during monomer deposition and for post-annealing, respectively. In
But monomers can also be specifically designed for heteromole- both cases, essentially all deposited monomers are transformed into the desired
cular coupling. This is illustrated in Fig. 4b–d with the tri-halogen- GNR structures.
functionalized monomer 1,3,5-tris(499-iodo-29-biphenyl)benzene STM characterization of GNRs. A variable-temperature STM and a low-
(monomer 3), which has C3 symmetry and provides no steric hind- temperature STM, both from Omicron Nanotechnology, were used to characterize
rance against radical addition to monomer 2 to yield the threefold the morphology of the GNR samples. Images were taken in the constant current
mode under ultrahigh-vacuum conditions at sample temperatures of 298 K (room
GNR junction seen in the STM image in Fig. 4b. The strategy of using
temperature), 115 K (liquid N2 cooling) or 35 K (liquid He cooling) in the variable-
two different precursor monomers designed for facile heteromole- temperature STM and 77 K or 5 K in the low-temperature STM.
cular coupling and cyclodehydrogenation should also enable the Monomer synthesis, spectroscopic characterization, DFT calculations.
controlled growth of GNR heterojunctions. Our bottom-up GNR Details regarding the synthesis of the precursor monomers, the Raman and
XPS experiments, DFT calculations and STM simulations are given in the
Supplementary Information.
a b
Received 14 January; accepted 24 May 2010.

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