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Angewandte
Eine Zeitschrift der Gesellschaft Deutscher Chemiker
Chemie
www.angewandte.de
Akzeptierter Artikel
Titel: Highly Crystalline Mesoporous C60 with Ordered Pores: A New
Class of Nanomaterials for Energy Applications
Autoren: Mercy Benzigar, Stalin Joseph, Hamid Ilbeygi, Dae-Hwan
Park, Sujoy Sarkar, Goutam Chandra, Siva Umapathy,
Sampath Srinivasan, Siddulu Talapaneni, and Ajayan Vinu
Dieser Beitrag wurde nach Begutachtung und Überarbeitung sofort als
"akzeptierter Artikel" (Accepted Article; AA) publiziert und kann unter
Angabe der unten stehenden Digitalobjekt-Identifizierungsnummer
(DOI) zitiert werden. Die deutsche Übersetzung wird gemeinsam mit der
endgültigen englischen Fassung erscheinen. Die endgültige englische
Fassung (Version of Record) wird ehestmöglich nach dem Redigieren
und einem Korrekturgang als Early-View-Beitrag erscheinen und kann
sich naturgemäß von der AA-Fassung unterscheiden. Leser sollten
daher die endgültige Fassung, sobald sie veröffentlicht ist, verwenden.
Für die AA-Fassung trägt der Autor die alleinige Verantwortung.
Zitierweise: Angew. Chem. Int. Ed. 10.1002/anie.201710888
Angew. Chem. 10.1002/ange.201710888
Link zur VoR: http://dx.doi.org/10.1002/anie.201710888
http://dx.doi.org/10.1002/ange.201710888
10.1002/ange.201710888
Angewandte Chemie
COMMUNICATION
Highly Crystalline Mesoporous C60 with Ordered Pores: A New
Class of Nanomaterials for Energy Applications
Abstract: Highly ordered mesoporous C60 with well-ordered porous
structure and a high crystallinity is prepared through the nanohard
templating method using saturated solution of C60 in 1chloronaphthalene (51 mg mL1) as a C60 precursor and SBA-15 as a
hard template. The high solubility of C60 in 1-chloronaphthalene helps
not only to encapsulate a huge amount of the C60 into the mesopores
of the template but also supports the oligomerization of C60 and the
formation of crystalline walls made of C60. The obtained mesoporous
C60 exhibits a rod shaped morphology, a high specific surface area
(680 m2 g1), tuneable pores, and a highly crystalline wall structure.
This exciting ordered mesoporous C60 offers high supercapacitive
performance and a high selectivity to H2O2 production and methanol
tolerance for ORR. We expect that this simple strategy could be
adopted to make a series of mesoporous fullerenes with different
structures and carbon atoms as a new class of energy materials.
Since the discovery of buckminsterfullerene (C60)1 by Kroto, Curl,
and Smalley, this new allotrope of carbon has been extensively
studied owing to its unique molecular structure and high
mechanical and photochemical stability2, 3. Fullerene materials
with organic or inorganic nanostructures offer much better
properties including unique semiconducting properties which
make them available for applications including electronics, solar
cells, and non-linear optics and also in medicinal chemistry4-9.
However, the poor textural properties due to the lack of porosity
and structural order of the fullerene nanostructures, limit their
applications in energy storage and conversion, adsorption and
separation and catalysis. Although there have been extensive
reports on the fabrication of other 2D materials such as graphene,
C3N4, h-BN, metals, metal oxides and MXenes mainly for energy
applications,10,11 the research on the preparation of 2D fullerene
based materials is quite limited. Researchers tried to use different
techniques including self-assembly to introduce porosity in the
fullerene nanostructures. Although they have succeeded in
[a]
[b]
[c]
M. Benzigar, S. Joseph, H. Ilbeygi, Dr. D.-H. Park, Dr. S. N.
Talapaneni and Prof. A. Vinu*
Future Industries Institute (FII), Division of Information
Technology Energy and Environment (DivITEE), University of
South Australia, Adelaide, SA 5095, Australia.
E-mail: Ajayan.Vinu@newcastle.edu.au
Dr. D.-H. Park, Dr. S. N. Talapaneni and Prof. A. Vinu
Global Innovative Center for Advanced Nanomaterials (GICAN),
Faculty of Natural Built Environment and Engineering, University
of Newcastle, Callaghan, NSW 2308, Australia.
Dr. S. Sarkar, Dr. G. Chandra, Prof. S. Umapathy, Prof. S.
Srinivasan
Department of Inorganic and Physical Chemistry and Department
of Instrumentation and Applied Physics
Indian Institute of Science.Bangalore 560 012, Karnataka, India.
creating porosity, they failed to obtain ordered porosity and
crystalline framework in fullerene based materials12-17. It is
expected that, highly crystalline mesoporous fullerene materials
can promise to even wider range of practical applications
including energy storage, sensing and is further considered as the
key factors that determine the final performance of the fullerene
nanostructures in energy storage, adsorption or separation and
drug delivery. Until now, no reports are available in the open
literature on the preparation of highly crystalline highly ordered
mesoporous fullerene materials.
Nanotemplating methods are widely known to create porosity
in carbons or metals or metal oxides18-23. Unfortunately, this
technique was not successful in creating ordered nanoporosity in
C60 due to the poor solubility of the C60 in most of the solvents24,
25
, which does not help to completely fill the void space of the
inorganic template used in the nanotemplating approaches. This
factor is the key as it helps to cross-link the C60 precursors and
finally obtain ordered porous structure after the removal of the
template. Another drawback of this technique is that the final
porous carbon products derived from this technique are often
amorphous in nature26, 27 which may not be attractive for practical
applications.
To overcome these issues, herein we present a new strategy to
create highly ordered mesoporous C60 with highly crystalline wall
structure by using highly solubilized C60 in chlorinated aromatic
solvent, 1-chloronaphthalene wherein the solubility of the C60 is
very high (51 mg mL1), through nanotemplating method in which
mesoporous silica SBA-15 was used as a template. The solvent
used here not only helps to completely fill the pores of the
templates but also support the easy polymerization through crosslinking the C60 which delivers the formation of highly crystalline
fullerene framework. These prepared mesoporous C60 exhibit
well-ordered porous structure with highly crystalline walls made of
C60 and a high specific surface area. We further demonstrate their
superior performance in energy storage with a high specific
capacitance and a high stability, and in oxygen reduction reaction
(ORR) as metal free catalysts, which is mainly due to their
polymerized and crystalline C60 network in the walls and
outstanding textural parameters including high specific surface
area and uniform pore size distribution. This unique and simplified
methodology can be extended for the formation of series of
mesoporous fullerenes with different carbon atoms and structure.
1-chloronaphthalene is a polar molecule with a dense aromatic
structure of polycyclic hydrocarbons. Fullerene is also a heavy
carbon molecule with complete aromaticity, it is anticipated that,
1-chloronaphthalene can solubilize the C60 molecule via aromaticaromatic interactions. As expected, fullerene C60 has high
solubility of 51 mg mL-1 in 1-chloronaphthalene solvent. The
interaction of 1-chloronaphthalene with the fullerene C60, primarily
makes the pentagon-pentagon fusion. This adjustment in the
pentagons is majorly attributed by the electrophilic aromatic
substitution reaction caused by 1-chloronaphthalene. In a typical
This article is protected by copyright. All rights reserved.
Accepted Manuscript
Mercy Benzigar,[a] Stalin Joseph,[a] Hamid Ilbeygi,[a] Dae-Hwan Park,[a,b] Sujoy Sarkar,[c] Goutam
Chandra,[c] Siva Umapathy,[c] Sampath Srinivasan,[c] Siddulu Naidu Talapaneni,[a,b] and Ajayan Vinu[a,b]*
10.1002/ange.201710888
Angewandte Chemie
synthesis, highly ordered mesoporous silica SBA-15 with different
pore diameters was mixed thoroughly with the fullerene C60
dissolved in the nonpolar organochlorine solvent, 1chloronaphthalene. The resultant mixture was carbonized directly
at 900 °C without any pre-heat treatment under the nitrogen
atmosphere to cross-link the C60. The template was finally
removed by washing with HF. As MFC60 materials are prepared
at 900 ̊C, they possess excellent thermal stability. Different
mesoporous C60 with different pore diameters were prepared by
using SBA-15 prepared at different temperature as the synthesis
temperature controls the pore diameter of the templates. The final
samples are denoted MFC60-T where T is the synthesis
temperature of the SBA-15.
Figure 1. a) Schematic illustration for the synthesis of polymerised mesoporous
C60 (MFC60). A) low angle and B) high angle XRD patterns of (a) MFC60-100 (b)
MFC60-130 (c) MFC60-150 and (d) MFC60-200 indicating highly ordered 2D
hexagonal mesoporous structure (P6mm symmetry) and polymerized C60
crystal structure through hard templating approach. C) and D) HR-TEM image
of MFC60-130 material at lower and higher magnification showing uniform rod
shaped morphology and super highly ordered mesostructure with clear lattice
fringes and pore walls.
The mesostructural order and the purity of the MFC60-100,
MFC60-130, and MFC60-150 prepared using SBA-15-100, SBA15-130, SBA-15-150, and SBA-15-200 respectively, was
confirmed by powder X-ray diffraction (XRD) patterns which show
a sharp peak at a lower angle and two additional minor higher
order peaks that can be indexed to (100), (110), (200) reflections
of a two-dimensional lattice (p6mm) symmetry (Fig. 1A and
Supplementary Fig. S1, A and B). These results indicate that the
C60 molecules are strongly interconnected by C60 rods and the
structural order of the SBA-15 template was replicated into the
MFC60-100, MFC60-130 and MFC60-150. But, the MFC60
synthesised at 200 ̊C exhibits only a broad peak denoting the
clear structural degradation. The presence of higher angle Bragg
reflections at the wide angle XRD patterns (Fig. 1B) reveals the
highly crystalline fullerene polymeric network along the walls of
the MFC60.
It is an interesting result as the mesoporous carbons prepared
by nanohard templating techniques reported so far show only a
broad (002) reflection which is linked to the amorphous nature of
the sample. However, the wide angle XRD patterns of the MFC60T clearly display three high intensity peaks centered at d = 0.829,
0.504, and 0.430 nm which correspond to the characteristic (111),
(220), and (002) reflections of polymerized and highly crystalline
C60 molecules28. The polymerization of the fullerene molecules is
promoted by the chlorinated aromatic solvent which not only
enhances the solubility of the C60 but also supports the fusion of
pentagon-pentagon rings of the C60 molecules. This is confirmed
by the fact that only partially crystalline or amorphous
mesoporous C60 was obtained when other solvents such as
trimethyl benzene are used (supplementary Fig. S2A and B).
When the templates with large pore diameters (supplementary
Fig. S1C and D) are used, only disordered mesoporous C60 with
crystalline walls is obtained. However, an increase in the pore
diameter of the samples is observed as the pore diameter of the
templates is increased. The d-spacing is increased from 9.69 nm
to 10.84 nm with increasing the synthesis temperature of the
template which dictates the pore diameter of the template. These
results indicate that proper choice of the template with optimized
pore diameter is critical to obtain highly crystalline MFC60 with
ordered porous structure as the pore diameter of the template
facilitates the density of the packing of C60 molecules, which are
critical for the interconnection between C60 in the micro channels.
HRTEM image of MFC60-130 clearly shows the presence of
highly ordered mesopores with the size of 4.5 nm that are created
by the dissolution of mesoporous silica template after washing
with HF (Fig. 1C and D). This result also reveals the ordered
porous structure separated by the polymerised thick C60 walls. All
the samples exhibit a type IV isotherm with a large hysteresis loop
associated with cylindrical pores, revealed from the capillary
condensation step, which is the typical characteristic of
mesoporous materials (Fig. S3A and B). It can also be clearly
seen that the capillary condensation step moves to the higher
relative pressure with the concomitant reduction in the amount of
adsorption at the monolayer as the pore diameter of the template
is increased. The specific surface area decreases from 680 m2
g1 to 480 m2 g1 with the concomitant increase of the pore
diameter from 4.5 to 10.6 nm, and specific pore volume from 0.60
to 0.85 cm3 g1 when the synthesis temperature of the template is
increased from 100 to 200 °C (Table 1S). The pore diameter
calculated from the nitrogen adsorption is quite consistent with the
data obtained from the HRTEM. The large pore volume of MFC60200 may be attributed to the large textural mesopores that are
originated from the incomplete polymerization or broken C60 walls
that form the large cavities. However, MFC60-200 registered the
lowest surface area which could be related to the structural
disorder in the sample. On the other hand, the high specific
surface area of the MFC60 prepared using the templates
synthesized at lower temperature could be linked with the small
pore diameter and the cylindrical pore system (pore diameter =
4V/A where V is the volume and A is the surface area). Among
This article is protected by copyright. All rights reserved.
Accepted Manuscript
COMMUNICATION
10.1002/ange.201710888
Angewandte Chemie
the samples studied, MFC60-130 registered the highest specific
surface area (680 m2 g1) and reasonable specific pore volume
(0.75 cm3 g1).
The scanning electron microscopy image shows that MFC60130 has a uniform rod shaped morphology with the width of 0.4
m and a length of 1.38 m (supplementary Fig. S4 a and b)
which is similar to that of the template prepared under static
condition, confirming the successful replication of the structure of
the template into C60. It should be noted that the surface
morphology of MFC60-130 is much better than that of other
samples. For example, MFC60-100 shows the non-uniform
clumped rods that are shorter in length and have craggy surface
whereas MFC60-150 exhibits the particles with different size and
shape. These results reveal that the hydrothermal temperature of
the template plays a vital role in fabricating highly uniform nanorods (Supplementary Fig. S4 c and d).
Figure 2. A) Synchrotron-based C 1s NEXFAS data of (a) C60 precursor (b)
MFC60-130 and (c) graphite confirming sp2 bonded structure. B) High resolution
XPS spectrum of MFC60-130 (inset - XPS survey spectrum). C and D) Raman
spectrum of (black curve) C60 precursor (a) MFC60-100 (b) MFC60-130 and (c)
MFC60-150.
The bonding on the wall structure of the MFC60-130 was
observed by NEXAFS and the results are compared with pure C60
(Fig. 2A). Pristine C60 displays four definite peaks at 284.2 (C1),
285.8 (C2), 286.2 (C3) and 288.3 (C4) eV which represent the
transition from 1s to the lowest unoccupied molecular orbitals
(LUMO), contributing to the 1s orbital excitation to final states of
π* resonant feature29. Likewise, the higher energy resonance
above 290 eV represents the excitation to final states of
photoexcited σ* character30. Interestingly, NEXAFS spectrum of
MFC60-130 shows broader π* resonance (C1 and C4) peaks with
a huge reduction in the intensity, confirming the polymerization of
C60 molecules along the wall structure. Similar result has been
also observed for the photopolymerised C60 polymers with nonporous structure31. The disappearance and convergence of C2
and C3 peaks into a broad single peak falling at 286 eV for MFC60130 also reveals that the carbon atoms are finally covalently
linked to a sequence of C60 cages, similar to the graphene shown
in Fig. 2A(c). Nature and coordination of C atoms in the MFC60130 was also analysed by a high resolution XPS and the results
are shown in Fig. 2B. As it can be seen from the deconvoluted
XPS C 1s spectrum, a significant fraction of sp2 C=C bonding at
284.1 eV (62.29 area %) and shake up satellite peak π-π* at
290.3 eV (10.10 area %) is observed for MFC60-130, whereas the
sp2 C-C bonding with the symmetric shape is observed at 284.8
eV (27.61 area %), confirming the bonding between the C60
molecules. These results of C1s spectrum from XPS are in
agreement with the published results of XPS studies on C60
molecules except the presence of C=C, that resulted from the
polymerised C6032. The similar trend was also observed for other
MFC60 materials (Supplementary Fig. S5). The survey spectrum
of MFC60-130 confirms the purity of the sample with nearly 98%
carbon and a small amount of oxygen which might have been
originated from the solvent used for washing the samples during
HF treatment.
The Raman spectra of Pristine C60, MFC60-100, MFC60-130,
and MFC60-150 are obtained using 514 nm laser as excitation
wavelength and the results are shown in Fig. 2C. The intense and
sharp peak at 1466 cm−1 is observed for pristine C60, which is the
characteristic of a monomer. On the other hand, a drastic
decrease in the intensity of this characteristic peak occurs after
polymerisation, and the peak has shifted to 1464 cm−1 (Fig. 2D),
corresponding to the pentagonal pinch Ag2 band of the C60.33
Moreover, the peak at 495.5 cm1 corresponding to Ag1 band was
completely disappeared after polymerisation and two broad peaks
at 1350 cm1 (E1g) and 1590 cm1 (B1g) vibrational modes
corresponding to D and G band could be observed. From these
vibrational modes, the defect site in graphitic carbon is calculated
from the D and G lines (ID/IG) where MFC60-130 had the ratio 0.82.
Therefore, the reduction in the ID/IG ratio confirmed that the
covalent bonds were let to resonance that converted the sp3
bonding to sp2 form. Multi-peak fitting of the Raman spectrum on
polymerised C60 was performed with Lorentzian function (Fig. S6).
The Raman spectrum of pristine C60 contains one peak around
1466 cm1 (monomer) whereas MFC60-130 exhibits two peaks at
around 1464 (dimer) and 1460 cm−1 (linear chains), confirming the
polymerization and the cross-linking of C60 in the wall structure.
Figure 3. A) CV of MFC60-130 at the oxygen and nitrogen saturated solution. B)
Linear sweep measurements of MFC60-130 at 5 mV s1 at different rotation rates
ranging from 100 to 2000 rpm. C) CV curves of MFC60-130 at different applied
current densities. D) Charge-discharge curves of MFC60-130 at different applied
current densities.
This article is protected by copyright. All rights reserved.
Accepted Manuscript
COMMUNICATION
10.1002/ange.201710888
Angewandte Chemie
The ORR activity of MFC60-130 was determined from the
three electrode cyclic voltammetry (CV) in N2 -saturated and O2 saturated 0.5 M KOH aqueous solutions at a scan rate of 10 mV
s1 (Fig. 3A). The voltammogram without any significant peak was
obtained in N2 saturated solution where O2 was absent. On the
other hand, the characteristic oxygen reduction peak at 0.75 V vs
reversible hydrogen electrode (RHE) was observed for the
sample when oxygen was in to the solution, suggesting that this
catalyst enables to reduce the oxygen. To assess the ORR
kinetics, rotating disc electrode (RDE) measurements were
carried out using linear sweep voltammetry (LSV) (Fig. 3B) at
different rotation speed and at constant scan rate 5 mV s1. It is
found that the limiting current density is increased with increasing
the rotation speed. Moreover, the ORR catalytic performance of
MFC60-130 is commenced at an onset potential of 0.82 and a half
wave potential of 0.76 V at 1600 rpm. To understand the ORR
kinetics further in detail, Koutecky–Levich (K-L) plots were drawn
and the number of electrons transferred per oxygen molecule was
determined to be ~2.5 at different potentials (Supplementary Fig.
S7 a), suggesting 2 electron pathway for ORR where oxygen was
reduced to form H2O2. In addition, the MFC60-130 achieved a
kinetic limiting current density of 10.3 mA cm2 at 0.57 V vs RHE.
The Tafel slopes of the MFC60-130 are at 73.9 mV dec1 at a
lower current density region and 229 mV dec1 at a higher current
density region (Supplementary Fig. S7d). The change in slope at
different current densities was attributed by the different type
(Temkin to Langmuir) of adsorbed oxygen species on the catalyst
surface. This also indicates that the overall ORR speed is
controlled by the surface reaction rate of the catalyst and the
obtained value is also in agreement with the electron transfer
numbers (Fig. S7b). It is worth to assume that this better ORR
activity is through the mass transfer in mesopores and the
exchange current density was 1.1x1011 A cm2 at lower current
density region. The current density of MFC60-130 showed no
significant shift after the addition of methanol, which suggested a
high selectivity against the methanol (Fig. S7 d).
MFC60-T
were
also
applied
as
electrodes
for
supercapacitance applications (Figure. 3 C-D and Supplementary
Fig. S8, S9). All the samples except the MFC60-200 show an
increase in the area of the rectangular curve with increasing the
scan rate up to 100 mV. This speculates that the ions from the
electrolyte is reversibly adsorbed by the fullerene walls, resulting
an exemplary capacitive performance. Moreover, the lowest
capacitance seen for MFC60-200 (Supplementary Fig. S8 B, curve
d) also signifies that the low surface area of the material having
large mesopores fails to support the adsorption and exchange of
ions from the electrolyte. Noticeably, the area of the CV and the
charge-discharge curve of the MFC60-130 increase with the
increasing scan rate from 3mV to 100 mV s1 (Fig. 3 C), and the
same sample shows a very less resistance at a high current
density of 10 A g1, revealing a good rate capability and less
polarisation (Fig. 3D). The specific capacitance achieved from the
discharge curve for MFC60-T samples ranges from 63 to 116 F g1
at the current density of 2 A g1 (Supplementary Fig. S8B). Among
the MFC60-T samples studied, MFC60-130 showed the highest
specific capacitance of 93 to 141 F g1 at the different current
densities ranging from 10 A g1 to 0.5 A g1. This high capacitance
can be attributed to the highly ordered porous structure and large
specific surface area with conducting fullerene wall. The cycle test
of the MFC60-130 at 50 mV s1 (Supplementary Fig. S9 A) did not
show any noticeable degradation even after 1000 cycles,
revealing that the mesoporous C60 has a good rate capability and
a high stability. This can be attributed to the presence of highly
conducting C60 polymeric walls with ordered and robust porous
structure. Finally, the specific capacitance of MFC60-130 was
compared with that of multiwalled carbon nanotube (MWCNT)
and activated carbon (AC) (Supplementary Fig. S9B). It has been
found that the performance of MFC60-130 is much better than
MWCNT and AC.
In conclusion, we have elegantly demonstrated on the
fabrication of mesoporous C60 with well-ordered structure, high
surface area and highly crystalline C60 wherein mesoporous SBA15 was used as the template and 1-chloronaphthalene as the
solvent for optimized thermal polymerization of C60 at 900 ºC. The
solvent used in the synthesis was the key not only for the
polymerization but also the crystallization of C60 molecules. The
final material was found to be an attractive metal free electrode
for dual purpose applications in supercapacitor and direct
methanol fuel cell, which could be due to the high surface area
together with the highly stable and conducting wall structure. The
specific capacitance of the prepared material is much higher than
that of commercial carbons and carbon nanotubes. We surmise
that the strategy presented here can be extended for the
fabrication of new series of porous fullerenes with different carbon
atoms and will make a revolution in the field of fullerene materials
and energy.
Keywords: Mesoporous • nanotemplating • SBA-15 • fullerene
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Angewandte Chemie
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COMMUNICATION
10.1002/ange.201710888
Angewandte Chemie
COMMUNICATION
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COMMUNICATION
Well-ordered mesoporous fullerene
with highly crystalline C60 walls
prepared through a combined strategy
of nano-templating and unique
polymerisation approach and its high
performance in energy storage and
conversion is demonstrated.
M. Benzigar, S. Joseph, H. Ilbeygi, D.-H.
Park, S. Sarkar, G. Chandra, S.
Umapathy, S. Srinivasan, S. N.
Talapaneni, A. Vinu*
Page No. – Page No.
Highly Crystalline Mesoporous C60
with Ordered Pores: A New Class of
Nanomaterials for Energy
Applications
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