Ordered structures and sub-5 nm line patterns from rod-coil hybrids containing oligo(dimethylsiloxane)

Article abstract of DOI:10.1039/d0cc04377j

Sub-5 nm ordered nanostructures including lamellar, double gyroid, and columnar phases are formed by a series of oligo(dimethylsiloxane) (ODMS)-based rod-coil liquid crystals with accurate molecular weights. Films with well-oriented line patterns can be obtained by substrate-induced directed self-assembly, which may be further used as lithographic templates.

Full text of DOI:10.1039/d0cc04377j

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Ordered Structures and Sub-5 nm Line Patterns from RodCoil
Hybrid Containing Oligo(dimethylsiloxane) †
Received 00th January 20xx,
Accepted 00th January 20xx
Weilu Yang , Wei Zhang , Longfei Luo , Xiaolin Lyu , Anqi Xiao, Zhihao Shen,* and Xing-He Fan*
DOI: 10.1039/x0xx00000x
Sub-5 nm ordered nanostructures including lamellar, double gyroid (Gyr), cylinders, and spheres can be formed.23 The
gyroid, and columnar phase are formed by series of intrinsic length scale is the molecular length, between 2 and 10
a
oligo(dimethylsiloxane) (ODMS)-based rodcoil liquid crystals nm.24 LCs have been successfully used in optics, electronics,
with accurate molecular weights. Films with well-oriented line and membranes.2
patterns can be obtained by substrate-induced directed self-
5, 26
assembly, which may be futher used as lithographic templates.
Directed self-assembly (DSA) of nanomaterials with highly
n m
Scheme 1 Chemical structures of synthetic Si -C -Rod.
ordered phase-separated structures is a kind of promising
candidate for generating line structures which can be used as
Oligo(dimethylsiloxane) (ODMS) is a kind of inorganic
building block which can act as a precursor to inorganic
1
-4
templates in electronic devices. The recent research target
of DSA is to enhance long-range order and decrease domain
silicone oxide via oxygen plasma oxidation, making it an
5
spacings. In the past decades, the self-assembly of block
27, 28
attractive etch mask.
ODMS is comprised of the silicone
4
, 6-8
copolymers (BCPs) has been widely investigated.
BCPs can
oxygen main chain and methyl substituents. Like
polydimethylsiloxane (PDMS), owing to its chemical
incompatibility and large surface tension mismatch with most
form different self-assembled structures by changing the block
9
, 10
ratio and annealing conditions.
However, the periodic sizes
formed by traditional BCPs are usually larger than 10 nm. To
obtain smaller feature sizes, high -low N BCPs usually difficult
organic
materials,
highly
ordered
nanostructured
29-31
morphologies can be formed by nanophase segregation.
The synthesis of discrete ODMS chains by the group of Meijer
has led to the development of ODMS LCs with interesting self-
1
1-14
to prepare are needed.
It is also challenging to form
defect-free structures with sharp phase boundaries.
Following the Moore’s law, the feature size of devices
27
assembly behaviors. For LCs consisting of ODMS and
1
5, 16
keeps reducing until sub-10 nm length scale.
Block
h
naphthalenediimides (NDIs), a hexagonal columnar (Col )
phase with a lattice parameter of 6.6 nm was formed. By
combining ODMS and an azobenzene core, smectic and
molecules composed of “hard” cores and “soft” chains with
precise molecular structures, are a combination of liquid
19
1
7-20
crystal (LC) science and BCP science.
The absence of
columnar LC phases with lattice parameters between 3.0 and
dispersity (Đ = 1.00) results in nanophase-separated structures
32
5
.1 nm were formed. Furthermore, rigid cores containing
with uniform sizes.1
7, 21
The introduction of LC mesogens can
azobenzene can be oriented by polarized light to control the
D orientation of sub-5 nm patterns from ODMS-containing
improve immiscibility and facilitate the formation of long-
range ordered structures. Furthermore, the discrete length of
flexible chains endows the capacity to tune the formation of
ordered structures.22 By the self-assembly of rodcoil LCs, a
variety of ordered LC mesophase structures including lamellae,
3
23, 33
LCs.
By introducing hydrogen bonding, sub-5 nm columnar
34
phases were formed. The ODMS molecules can also be
introduced to polymer side chains by hydrogen bonding to
34
generate hierarchically self-assembled structures.
Although there are some researches on the bulk self-
assembled structures of ODMS-containing LCs, little research
has been done about the regulation of self-assembled
structures of such LCs within 5 nm. Herein, novel organic-
inorganic LCs composed of ODMS and a rod-shaped molecules,
Si -C -Rod (Scheme 1) (n represents the number of repeating
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer
Chemistry and Physics of Ministry of Education, Center for Soft Matter Science
and Engineering, and College of Chemistry and Molecular Engineering, Peking
University, Beijing 100871, China.
E-mail: zshen@pku.edu.cn; fanxh@pku.edu.cn
n
m
†Electronic Supplementary Information (ESI) available: Experimental section;
units in ODMS, while m represents the length of the linking
alkyl chain) were synthesized and explored. The rod-shaped
synthetic procedures; preparation of thin films; thermal transition data;
Schemes S1, S2; Table S1; Fig. S1-S22. See DOI: 10.1039/x0xx00000x
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2
o
segregation between the ODMS and organic parts. At 180 C,
View Article Online
DOI: 10.1039/D0CC04377J
all the diffraction peaks disappear; therefore, Si -C -Rod turns
3 4
into the Iso state.
At ambient temperature, five diffraction peaks with q =

1
1
.51
of Si
440) diffractions of a Gyr structure. The peaks in the higher-
angle region (Fig. S12) may be attributed to the crystal of the
rigid part. Therefore, Si -C -Rod forms a gyroid-crystal
,
1.74
, 2.77, 3.06, and 3.50 nm in the WAXS profile (Fig. 1b)
7
-C -Rod can be indexed as (211), (220), (420), (422), and
4
(
7
4
coexisting (K-in-Gyr) phase in which the block molecule as a
whole forms the Gyr structure and the rigid rod crystallizes.
The cell parameter of the Gyr structure is a = 10.34 nm. At 120
o
C, two diffraction peaks at q = 1.70 and 1.91 nm1 can be
indexed as (211) and (220) diffractions of a Gyr phase. The
peaks in the higher-angle region disappear (Fig. S12). The cell
parameter of the Gyr structure a decreases to 9.26 nm,
possibly owing to the more interdigitated packing mode of the
siloxane chains. At higher temperatures the siloxane chains are
like to have a higher degree of interdigitation, leading to a
decrease in the cell parameter. At 180 oC, all the peaks
disappear; thus, the sample enters into the Iso state.
Fig. 1 Temperature-dependent WAXS profiles of Si
3
-C
4
-Rod (a; the two peaks at q =
2.10 nm and 14.72 nm1 are attributed to the diffractions of aluminum foil during
1
1
7 4 4 7 8
testing), Si -C -Rod (b), Si11-C -Rod (c), and Si -C -Rod (d); Schematic diagram of the
phase transition of LCs during the heating process (e).
core contains a triple bond linked with two diphenyl groups,
resulting in an elongated LC core. In order to regulate the self-
assembled structures, the volume fraction of ODMS was varied.
Synthetic procedures are described in Electronic
For Si11-C
4
-Rod, five diffraction peaks with q = 1.34
,
1.43
c) at
,
Supplementary Information (Scheme S
1, S2). The final

1
2
.39
,
2.69, and 3.59 nm in the WAXS profile (Fig.
1
products, ODMS-containing rodcoil LCs were fully
ambient temperature can be indexed as (02), (11), (13), (04),
and (15) diffractions of a rectangular columnar (Col ) structure.
1
13
characterized by H NMR (Fig. S
1, S3, S5, S7), C NMR (Fig. S2,
r
S4
, S , S ), and matrix-assisted laser desorption/ionization
6
8
The cell parameters are a = 4.93 nm and b = 9.37 nm. The peak
related to π-π stacking could not be found in the higher-angle
region (Fig. S13), revealing that the rigid cores are relatively
disordered. At 100 oC, the above-mentioned diffraction peaks
still remain with a little variation in the peak positions (q =
time-of-flight (MALDI-TOF) mass spectra.
Thermogravimetric analysis (TGA) curves (Fig. S9) show
that the decomposition temperatures at 5% weight loss all
o
exceed 350 C. Differential scanning calorimetry (DSC) results
illustrate that the LCs Si
S10b), and Si11-C -Rod (Fig. S10c) have two phase transitions
whereas Si -C -Rod (Fig. S10d) only exhibits one phase
transition. In combination with polarized light microscopy
PLM) micrographs (Fig. S11a, b, c, d, e and f), during the
heating process, the transition of Si -C -Rod and the second
transitions of Si -C -Rod, Si -C -Rod, and Si11-C -Rod
correspond to the LC-isotropic (Iso) transition, while the first
transitions of Si -C -Rod, Si -C -Rod, and Si11-C -Rod are the
3 4 7 4
-C -Rod (Fig. S10a), Si -C -Rod (Fig.

1
1
.48, 1.60, 2.64, 2.95, and 3.96 nm ). Therefore, it forms a Col
r
4
phase with smaller cell parameters of a = 4.43 nm and b = 8.49
nm than those at ambient temperature. The shape of
rectangular arrays (b to a ratio = 1.91) remains unchanged,
which means that the packing mode stay the same. We define
7
8
(
7
8
the two types of Col
at lower and higher temperatures as Col
r
phases with a variation of cell parameters
-I and Col -II,
3
4
7
4
4
r
r
separately. The decrease in periodic sizes may also be
attributed to the higher degree of interdigitation of the flexible
siloxane chains. At 180 oC, all the diffraction peaks disappear,
indicating that the sample turns into the Iso phase.
3
4
7
4
4
crystal-LC, crystal-LC, and LC-LC transitions, respectively.
Self-assembled structures of these LCs in bulk were
determined by wide-angle X-ray scattering (WAXS). At ambient
temperature, four diffraction peaks in the WAXS profile (Fig.
For Si
2.99 3.96, and 4.50 nm can be indexed as (10), (11), (20),
21), and (30) diffractions of a Col structure at ambient
7 8
-C -Rod (Fig. 1d), five diffraction peaks at q = 1.47,

1
2
(
.56
,
,

1
1
1
a) with q = 2.16, 4.39, 6.57, and 7.76 nm have a q ratio of
:2:3:4. Sharp peaks in the higher-angle region may be
h
temperature. And the cell parameter is a = 4.86 nm. The
absence of the peak related to π-π stacking in the higher-angle
region (Fig. S14) reveals that the rigid rods are relatively
disordered. At 180 oC, all the peaks disappear, suggesting that
it turns into the Iso phase.
The above results indicate that the self-assembled
structures and periodic sizes can be controlled by tuning the
length of the ODMS tails. A schematic phase diagram of all
attributed to the crystalline structure of the rigid-rod units.
Therefore, Si -C -Rod forms a lamellae-crystal coexisting (K-in-
3
4
Lam) phase in which the whole rodcoil block molecule forms
the lamellar (Lam) structure and the rod part crystallizes. And
o
the large periodic size is d = 2.87 nm. At 150 C, two diffraction

1
peaks at q = 2.16 and 4.39 nm can be indexed as (10) and
(20) diffractions. Sharp peaks in the higher-angle region
o
disappear. Therefore, Si
3
-C
4
-Rod forms a Lam phase at 150 C.
four LCs with represent to temperature is depicted in Fig. 1e.

1
One diffuse scattering halo at q = 9 nm is originated from the
With temperature increasing from ambient temperature to
mean distance between siloxane units, while the other at q =
o
1
80 C, Si
3
-C
4
-Rod goes through the phase transitions from K-
-C -Rod has two phase
1
1
3 nm comes from the mean distance between the
in-Lam to Lam, then to Iso; Si
7
4
hydrocarbon chains. These two halos confirm the nanophase
2
| J. Name., 2012, 00, 1-3
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Fig. 2 Schematic models of different phase structures, K-in-Lam (a), Col
d), and the schematic of structural units (e). The green boards, the blue lines, and the
orange lines represent the rigid cores, alkyl chains, and ODMS chains, respectively.
r h
(b), Col (c), Gyr
(
Fig. 3 AFM phase image of the thin film of Si
phase image (c) of the thin film of Si11-C
image (e) of the thin film of Si -C -Rod, and AFM phase image of Si11-C
4
7
-C
4
-Rod (a), GI-WAXD pattern (b) and AFM
4
-Rod, GI-WAXD pattern (d) and AFM phase
-Rod thin film
7
8
transitions, one from K-in-Gyr to Gyr, and the other from Gyr within graphoepitaxial trenches of ≈132 nm width (f).
to Iso; Si11-C
Col -I to Col -II, then to Iso; Si
transition from Col to Iso.
Schematic packing models are shown in Fig.
phase, the rigid cores are aligned to form layer structures
green), while the ODMS chains in orange are arranged into
the other sublayers in an interdigitated manner (Fig. a). In the
4
-Rod also undergoes two phase transitions from
-C -Rod only exhibits one phase
which illustrates that the Lam structure has a parallel
orientation with respect to the Si substrate. Atomic-force
microscopy (AFM) height image (Fig. S17) shows flat sheets
with height difference of roughly an integer multiple of 2.9 nm
between two layers. This value is consistent with the d value (d
r
r
7
8
h
2
. In the Lam
(
=
2.87 nm) of the K-in-Lam phase in bulk.
For the thin film of Si -C -Rod, the arcs in the GI-WAXD
pattern (Fig. S18) can be indexed as (211), (220), (420), and
422) diffractions. AFM phase images (Fig. a) exhibit highly
2
7
4
columnar phases, the rigid rods are arranged to form the core
of the column (green), while the flexible ODMS chains in
orange fill the space between the cylinders (Fig. 2b and 2c). In
the Gyr phase, the rigid cores are arranged into the Gyr
networks, while the flexible ODMS chains in orange fill the
space between tubes (Fig. 2d). With the increase in the coil
(
3
ordered line features corresponding to the columnar structure
with a parallel orientation. An ODMS wetting layer in the air
interface should be formed because the surface energy of the
−
1 2
PDMS
ODMS tails is assumed to be very low (γ = 20.5 mNm ).
volume fraction, the self-assembled structure changes from
the higher-ordered crystal and LC coexisting structures to
Therefore the Gyr phase in bulk disappears in thin films.
Because these cylindrical structures are buried inside the
ODMS wetting layer, the contrast in the AFM phase images
comes from the different mechanical characters of the flexible
ODMS tails and the rigid cores in the tapping mode (rigid core
lower-ordered Col
be explained by the volume taken up by the coil fraction (fcoil
analogous to the self-assembly of rodcoil BCPs. Si -C -Rod
0.63 which is asymmetric but more or less close to
r h
or Col phase. These phase transitions can
)
3
4
with fcoil
=
=
light part, ODMS = dark part). The distance between adjacent
lines is ca. 4.20 nm which is in accordance with the d-spacing (d
4.16 nm) value calculated from the WAXS data.
For the thin film of Si11-C -Rod, the diffractions in the GI-
WAXD pattern (Fig. b) can be indexed as (02), (11), (13), (04),
15), and (06) of a Col structure having a parallel orientation
with respect to the Si wafer. Line patterns (Fig. c) are also
0
.5 assembles into a Lam structure. Si
which is relatively asymmetric forms a Gyr phase. Si11-C
0.84 and Si -C -Rod with
asymmetric form cylindrical structures (a Col
7
-C
4
-Rod with fcoil
=
0.78
-Rod
4
=
with fcoil
=
7
8
f
coil
=
0.80 which are more
phase and a Col
4
r
h
3
phase, respectively). With increasing number of carbons in the
linkage chain between the rigid rod and ODMS chains, the
melting temperature significantly decreases whereas the LC-
Iso transition temperature is increased, resulting in increased
LC temperature range, which can be attributed to the less
flexible property of the hydrocarbon chains compared to
siloxane chains. The increase in the overall fraction of flexible
chains results in the enhanced LC stability, also as expected.
(
r
3
easily found in AFM phase images in the tapping mode with a
distance of ca. 4.95 nm which is corresponding to the lattice
parameter a (a = 4.93 nm) of the Col phase calculated by bulk
r
WAXS data. Lines with a distance of the lattice parameter b are
not found, suggesting a preferential orientation of the
columnar lattice with the a-axis parallel to the substrate and
the b-axis perpendicular to the substrate.
A solution of
1
wt% LC in n-heptane was coated on a Si
5000 Da) polymer brush to
wafer decorated with a PDMS (M
n
=
For the thin film of Si
WAXD pattern (Fig. 3d) can be indexed as (10), (11), (20), and
30) of a Col structure having a parallel orientation with
represent to the Si wafer. AFM phase image (Fig. 3e) shows
highly ordered line features corresponding to a Col structure
7 8
-C -Rod, the diffractions in the GI-
prepare a uniform film. PDMS was chosen to increase the
compatibility of the sample and the substrate. The thicknesses
of the thin films were ca. 86 nm on the basis of the cross-
sectional images of scanning electron microscope (SEM) (Fig.
(
h
h
S
15). It is important to note that no annealing steps were
applied. For the thin film of Si -C -Rod, the grazing-incidence
wide-angle X-ray diffraction (GI-WAXD) pattern (Fig. S16
with parallel orientation. The distance between adjacent lines
is ca. 4.89 nm which is in accordance with the value of a (a =
4
3
4
)
.86 nm) obtained from WAXS results. Moreover, all these line
x
shows that the (10) diffraction is located along the q direction,
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Jung, Adv. Funct. Mater., 2019, 29, 1901876.
7 4 4 7 8
patterns of the films of Si -C -Rod, Si11-C -Rod, and Si -C -Rod
View Article Online
6
. S. Rasappa, L. Schulte, D. Borah, H. Hulkkonen, S. Ndoni, T.
DOI: 10.1039/D0CC04377J
can be found clearly in large areas with few defects (Fig. S19,
S20 and S21). However, the large-area ordering still needs to
be further improved because these lines are in multidomains.
And as demonstrated by the appearance of equatorial arcs in
the 2D GI-WAXD patterns the alignment of the lines is still not
perfect. Schematic models of the molecular alignment in both
the layer structures and line patterns at the air-LC and LC-
PDMS interfaces are provided in Fig. S22. We further
Salminen, R. Senthamaraikanan, M. A. Morris and T. Niemi,
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4
Schweitzer, T. Hayakawa, C. O. Osuji and P. Gopalan,
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of ≈132 nm in width decorated on a silicone substrate. AFM
result reveals multi-line patterns confined inside these
trenches paralleled to the trench walls (Fig. 3f). The distance
between two adjacent lines is ca. 4.95 nm which matches the
value of the a parameter (a = 4.93 nm) calculated by WAXS
results. Therefore, such trenches can be used to effectively
align the self-assembled structures of the abovementioned
LCs.
1
1
1
4. W. J. Durand, G. Blachut, M. J. Maher, S. Sirard, S. Tein, M. C.
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1
5. G. E. Moore, Electronics, 1965, 38, 114-117.
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1
7. B. Oschmann, J. Lawrence, M. W. Schulze, J. M. Ren, A.
Anastasaki, Y. Luo, M. D. Nothling, C. W. Pester, K. T.
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Si -C -Rod were synthesized. When the number of carbon
7
8
atoms in the linking alkyl chain remains constant as 4, with the
increase of the number of siloxane repeating units in ODMS,
their self-assembled structure changes from Lam to Gyr, then 18. J. A. Berrocal, J. Teyssandier, O. J. G. M. Goor, S. De Feyter
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to Col
constant as 7, with the increase of the length of the linking
alkyl chain, the self-assembled structure changes from Col to
Col . For the Lam and columnar structures, their bulk
assembled structures can be well transferred onto the thin
films, and parallel-orientated supramolecular layers and
columns with sub-5 nm line patterns can be obtained.
However, the Gyr phase in bulk cannot be retained and is
transformed to line patterns in thin films. The line width can
r
. When the number of siloxane repeating units remains
1
2
r
h
2
2
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well-ordered line patterns can be further aligned in
graphoepitaxial trenches.
This work was supported by the National Key R&D
Program of China (Grant 2018YFB0703702) and the National
2
2
2
5. T. Kato, J. Uchida, T. Ichikawa and T. Sakamoto, Angew.
Chem. Int. Ed., 2018, 57, 4355-4371.
Natural Science Foundation of China (Grants 51725301, 26. J. Lugger, D. J. Mulder, R. Sijbesma and A. Schenning,
Materials, 2018, 11, 104-121.
2
1674004, and 51921002).
2
7. B. van Genabeek, B. F. M. de Waal, M. M. J. Gosens, L. M.
Pitet, A. R. A. Palmans and E. W. Meijer, J. Am. Chem. Soc.,
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016, 138, 4210-4218.
Conflicts of interest
There are no conflicts to declare.
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DOI: 10.1039/D0CC04377J
Oligo(dimethylsiloxane)-based rodcoil liquid crystals can form
lamellar, double gyroid, and columnar phases that can also be
transferred onto silicone substrate and oriented by modified
trenches.
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