Synthesis and characterization of biphenyl liquid crystal based on natural molecules and 2(5H)-furanone moiety

Article abstract of DOI:10.1007/s11164-012-0777-5

Using 4′-hexyloxybiphenyl-4-ol and N-(5-alkoxy-3-bromo-2(5H)- furanonyl) amino acids as reactants, a series of novel biphenyl liquid crystal compounds containing natural molecule moieties, such as menthol, borneol, and amino acids, were synthesized via esterification. The structures of all novel compounds were confirmed by FTIR, ¹H NMR, ¹³C NMR, MS, and elemental analysis, and the liquid crystal properties of target compounds were characterized with DSC, XRD, and POM. The introduction of hexyloxy made the biphenyl esters have a potential to appear in mesomorphic phase and have a higher Tm, and bornyl moiety was more beneficial for the liquid crystal performance than a menthyl unit. Most compounds were mesomorphic phase liquid crystal molecules, and POM and XRD showed that they existed in smectic phase. These researches provide a theoretical basis for the synthesis of biphenyl ester liquid crystal materials via the utilization of 2(5H)-furanone derivates and natural molecules.

Full text of DOI:10.1007/s11164-012-0777-5

Res Chem Intermed (2013) 39:2513–2526
DOI 10.1007/s11164-012-0777-5
Synthesis and characterization of biphenyl liquid
crystal based on natural molecules and 2(5H)-furanone
moiety
•
•
•
Shi-He Luo Qun-Fang Wang Zhao-Yang Wang
Pai Peng
Received: 15 July 2012 / Accepted: 17 August 2012 / Published online: 1 September 2012
Ó Springer Science+Business Media B.V. 2012
Abstract Using 40-hexyloxybiphenyl-4-ol and N-(5-alkoxy-3-bromo-2(5H)-fur-
anonyl) amino acids as reactants, a series of novel biphenyl liquid crystal com-
pounds containing natural molecule moieties, such as menthol, borneol, and amino
acids, were synthesized via esterification. The structures of all novel compounds
were confirmed by FTIR, 1H NMR, 13C NMR, MS, and elemental analysis, and the
liquid crystal properties of target compounds were characterized with DSC, XRD,
and POM. The introduction of hexyloxy made the biphenyl esters have a potential to
appear in mesomorphic phase and have a higher Tm, and bornyl moiety was more
beneficial for the liquid crystal performance than a menthyl unit. Most compounds
were mesomorphic phase liquid crystal molecules, and POM and XRD showed that
they existed in smectic phase. These researches provide a theoretical basis for
the synthesis of biphenyl ester liquid crystal materials via the utilization of
2(5H)-furanone derivates and natural molecules.
Keywords Biphenyl ester ꢀ 2(5H)-furanone ꢀ Liquid crystal ꢀ Synthesis ꢀ
Amino acid ꢀ Menthol ꢀ Borneol
Introduction
Biphenyls liquid crystals have been widely used in photoelectric display materials and
other application areas for their many advantages, e.g., good physical and chemical
stability, wide temperature range, appropriately low viscosity, fast response, and low
Electronic supplementary material The online version of this article (doi:
10.1007/s11164-012-0777-5) contains supplementary material, which is available to authorized users.
S.-H. Luo ꢀ Q.-F. Wang ꢀ Z.-Y. Wang (&) ꢀ P. Peng
School of Chemistry and Environment, South China Normal University,
Guangzhou 510006, People’s Republic of China
e-mail: wangwangzhaoyang@tom.com; wangzy@scnu.edu.cn
123

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S.-H. Luo et al.
driver voltage [1–6]. Especially, their alkoxy derivates could have a potential to afford a
huge birefringence which will be beneficial to their optical performances [7]. Therefore,
more and more researches have been focused on alkoxy biphenyls used in liquid
crystalline areas [8–13].
On the other hand, chiral liquid crystal materials have many unique photoelectric
performance, such as good optical properties, reflection choice for polarized light,
circular dichroism, ferroelectricity, and piezoelectricity, which make them have vast
potential application prospects in many fields, including non-linear optics, snap
switch, microelectronics, etc. [14–17]. Thus, there are more and more reports on the
introduction of different chiral moieties, such as menthyl [18–22], bornyl [23, 24],
and amino acid units [25–27], into liquid crystal materials.
However, even introducing chiral menthyl [20, 22, 28, 29] or bornyl [24] into
biphenyl liquid crystal materials became a new research direction, and there are few
papers reporting the design and synthesis of biphenyl liquid crystals simultaneously
containing chiral menthyl/bornyl and amino acid units, let alone alkoxy biphenyls.
More importantly, it has been found that 2(5H)-furanone derivates could be used in
liquid crystal research today [30, 31].
Therefore, on the basis of our previous work [31], in order to further expand the
applications of 3,4-dihalo-2(5H)-furanone [31–34], a series of novel liquid crystal
compounds 3 were here designed and synthesized via the esterification of 40-
hexyloxybiphenyl-4-ol2withN-[5-alkoxy-2(5H)-furanonyl]aminoacids1(Scheme 1).
The structures and liquid crystal properties of the target compounds 3a–3p were
systematically characterized by FTIR, 1H NMR, MS, DSC, XRD, and POM.
Results and discussion
Syntheses of target compounds by esterification
The traditional esterification process of phenols via the first acylation of carboxylic
acids and then the dehydrohalogenation between acyl chloride and phenols produces
Br
Br
2
O
OC6H13
14
11
4
3
15
13
7
H
10
6
R'
H
R'
H
R'
H
O
5
O
9
8
1
COO
Br
12
COOH
Br
COOH
R-HN
2
RN
H
RN
H
HO
DCC, DMAP
KOH, EtOH, r.t.
Br
O
Br
H
Reflux in CH2Cl2
O
4
3
O
O
1a~1p
R*O
R*O
OC6H13
2
3a~3p
10
O
5
O
O
h: n=1, R=R'=H, R*=B*
1
i: n=1, R=H, R'=CH2CH(CH3)2, R*=M*
j: n=1, R=H, R'=CH(CH3)2, R*=M*
k: n=5, R=R'=H, R*=M*
a: n=1, R=H, R'=CH2CH(CH3)2, R*=B*
b: n=1, R=H, R'=CH(CH3)2, R*=B*
c: n=5, R=H, R'=H, R*=B*
(M*),
(B*)
R*=
l: n=1, R=CH3, R'=H, R*=M*
m: n=1, R=H, R'=CH2Ph, R*=M*
n: n=1, R=H, R'=Ph, R*=M*
o: n=3, R=R'=H, R*=M*
d: n=1, R=CH3, R'=H, R*=B*
e: n=1, R=H, R'=CH2Ph, R*=B*
f: n=1, R=H, R'=Ph, R*=B*
g: n=3, R=R'=H, R*=B*
p: n=1, R=R'=H, R*=M*
Scheme 1 Synthetic route to target compounds 3a-3p
123

Synthesis and characterization of biphenyl liquid
2515
a large number of corrosive gases, such as sulfur dioxide and hydrogen chloride.
Therefore, there are more and more reports on another relatively green esterification
method via the dehydrating condensation between carboxylic acids and phenols
[35]. In this work, we still chose the latter esterification method for the syntheses of
the target compounds 3.
However, this time, we used more available N,N0-dicyclohexylcarbodiimide
(DCC) as dehydrating agent, though its by-product 1,3-dicyclohexylurea was
sometimes difficult to remove clearly. Similarly, more common and cheaper
N,N-dimethylaminopyridine (DMAP) was selected as catalyst. At the same time, the
suitably higher reaction temperature than that reported before (room temperature)
[31] was advantageous. And fortunately, the yields (29–55 %) of products 3 are also
generally higher than before (16–25 %) [31], which may be linked to the existence
of hexyloxy in biphenyl-4-ol because of its electron-donating effect for phenoxy
anion in the reaction.
Of course, due to the lower activity of the phenolic hydroxyl group used here for
esterification, some careful operations, especially the patient drying pretreatment to
the reaction flask, were very necessary. These experiences came from the
investigations on an unexpected by-product 3e0 (Scheme 2). During the operation
for the synthesis of target compound 3e, trace alcohol was mixed into the reaction
systems by mistake in the drying pretreatment. As a result, a product with obviously
lower yield was obtained. And its following characterization data were also puzzling.
3e0: Yellowish solid, yield 13 % (calculated according to the reactant 1e); m.p.
1
149.5–151.6 °C; H NMR (400 MHz, CDCl3-TMS) d: 0.84–0.88 (9H, m, CH3-12,
CH3-14, CH3-15), 1.23–1.33 (7H, m, CH2-8, CH2-9, CH3-27), 1.60–1.65 (2H, m,
CH2-11), 2.10–2.25 (1H, m, CH2-10), 3.05–3.35 (2H, m, CH2-18), 3.50–3.89
(1H, m, CH-6), 3.97–4.69 (3H, m, CH-17, CH2-26), 5.12–5.66 (2H, m, CH-5, NH),
7.10–7.19 (2H, m, ArH-20,24), 7.27–7.39 (3H, m, ArH-21,22,23); ESI–MS m/z (%):
508 ([M ? H]?, 14.0), 530 ([M ? Na]?, 30.0); Anal. Calcd for C25H32BrNO5: C
59.29, H 6.37, N 2.77, found: C 59.15, H 6.27, N 2.58.
1
Surprisingly, there were no typical peaks from the biphenyl groups in the H
NMR characterization. Especially, the results of MS were not the same as expected.
In the end, combining the analysis on all operations, we confirmed that the
CH2Ph
COO
HN
H
Br
H
CH2Ph
COOH
HO
O
O
O
HN
H
Br
H
OC6H13
DCC, DMAP
3e (yield 0%)
Reflux in CH2Cl2
CH2Ph
+
O
O
O
C2H5OH (trace,
mixed into the
reaction systems
by mistake)
OC6H13
COOC2H5
Br
1e
2
HN
H
O
H
O
O
3e' (yield 13%)
Scheme 2 The production of unexpected compound 3e
123

2516
S.-H. Luo et al.
compound was the by-product 3e0. It was the result of the reaction of the trace
alcohol with intermediate 1e, because aliphatic alcohol preferentially reacted with
the carboxyl group in N-[5-alkoxy-2(5H)-furanonyl] amino acid. In a word, target
compounds 3 must be carefully synthesized with enough patience.
Structure characterization of all new compounds
In the IR spectra, stretching absorption of the N–H groups was observed in the
region 3,400–3,310 cm-1 except for 3d and 3l. Stretching absorption bands of
saturated C–H groups were observed in the region 2,960–2,950 cm-1, while for
unsaturated C–H groups, the region was 3,070–3,000 cm-1. The strong C=O
stretching band appeared at 1,785–1,705 cm-1. The C=C stretching band in 2(5H)-
furanone ring usually occurred in the 1,660–1,620 cm-1 region, and the benzene
ring skeletal stretching occurred at 1,600–1,450 cm-1
.
1
In H NMR, there was a singlet at 5.25–5.96 ppm from the 5-H of 2(5H)-
furanone. And there were a series of peaks at 6.90–7.60 ppm from the biphenyl
groups. Due to the occurrence of unexpected product 3e0, in order to further confirm
the structure of new compounds, two compounds (3c, 3k) were randomly chosen as
representatives to be characterized with 13C NMR. There were a series of peaks at
114.8–138.7 ppm from the biphenyl groups in their 13C NMR spectra. Furthermore,
there was a peak at 98.6–99.1 ppm from the 5-C of 2(5H)-furanone.
Therefore, combining with the results of mass spectroscopy and elemental
analysis, these characterizations proved the structures of all newly synthesized
compounds 3 were correct as expected.
Liquid crystal characterization of target compounds
The liquid crystal properties of target compounds 3 were characterized with DSC,
XRD, and POM. Using the DSC curve of compound 3c as a representative, there are
two endothermic peaks on the curve of heating (Fig. 1), which indicates a series of
different phase transformations. Especially, it could be obviously seen that the
melting point (the melting temperature, Tm) was 60.1 °C and the clear point (the
isotropic temperature, Ti) was 147.6 °C. The transition temperatures and enthalpies
of different compounds 3 are summarized in Table 1.
Compared with the previous similar reports on N-[5-menthoxy-2(5H)-furanonyl]
amino acid biphenyl ester liquid crystal compounds [31], the introduction of
hexyloxy made the biphenyl esters have a potential to appear in mesomorphic phase
(e.g. 3i, 3l, 3o) and have a higher Tm (e.g. 3j, 3n). At the same time, it could be
found that the compounds containing bornyl usually had a higher Tm than those
with a menthyl structure (e.g., 3a vs. 3i, 3f vs. 3n, 3g vs. 3o). This may be due to the
obvious rigid polycyclic structure in the bornyl moiety.
However, the influences of amino acid units in the new target compounds were
similar to our previous work [31]. For example, with the decrease of alkyl chain
length in amino acid units, the new compounds (e.g., 3k vs. 3o) were more likely to
appear as mesomorphic phase.
123

Synthesis and characterization of biphenyl liquid
2517
Fig. 1 The DSC curve of target
compound 3c
Table 1 The transition temperatures and enthalpies of target compounds 3
Compounds
The transition temperature T/ °C (enthalpies, DH/J g-1
)
Heating
Cooling
3a
3b
3c
3d
3e
3f
Cr 77.7 (0.9) Sm 120.1 (2.4) I
–
I 104.5 (-1.6) Sm 66.3 (-1.1) Cr
I 87.9 (-0.45) Cr
I 124.0 (-0.7) Sm 70.0 (-16.9) Cr
I 72.9 (-3.9) Cr
Cr 60.1 (6.3) Sm 99.7 (0.5) Sm 147.6 (41.7) I
Cr 109.3 (1.4) I
Cr 58.6 (3.23) I
I 44.9 (-8.2) Cr
Cr 112.1 (2.5) Sm 158.4 (1.4) I
Cr 99.7 (0.9) Sm 144.0 (6.6) I
Cr 68.3 (0.6) Sm 105.8 (0.2) I
Cr 39.9 (3.9) Sm 60.0 (9.1) Sm 120.4 (-12.5) I
Cr 76.0 (3.5) Sm 120.3 (0.7) I
Cr 120.1 (1.7) I
I 151.8 (-0.7) Cr
I 76.7 (-2.4) Cr
3g
3h
3i
I 104.9 (-0.2) Sm 54.3 (-1.2) Cr
I 41.05 (-12.5) Cr
I 48.5 (-0.68) Cr
I 112.7 (-0.7) Sm 48.7 (-0.5) Cr
–
3j
3k
3l
Cr 73.52 (1.2) Sm 97.58 (5.3) I
Oil
3m
3n
3o
3p
Oil
Cr 71.9 (1.4) Sm 120.5 (2.0) I
Cr 57.2 (1.7) Sm 127.5 (7.0) I
Oil
I 42.3 Cr
I 107.0 (-14.9) Sm 45.6 (-3.5) Cr
Oil
Using 3c as a representative of novel biphenyl ester liquid crystal compounds 3,
their liquid crystal properties were further confirmed with XRD. And the XRD
spectrum of the compound 3c under room temperature is shown in Fig. 2. Generally,
for the liquid crystalline molecules displaying smectic, nematic, or cholesteric phase,
there is a significant diffraction peak near 20°, but only the smectic phase liquid
crystal molecule has another diffraction peak near 6°. Therefore, the XRD result
shows that the compound 3c may appear in smectic phase [36, 37].
In common, the liquid crystal compounds showing different transition temper-
atures and enthalpies in DSC curve could also be verified with variable temperature
XRD. The XRD spectra of the compound 3c under different temperatures are shown
in Fig. 3. With the increase of the temperature, the diffraction peak near 20°
123

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S.-H. Luo et al.
Fig. 2 The XRD spectrum of
2(5H)-furanone compound 3c
Fig. 3 The XRD spectra of 2(5H)-furanone compound 3c at different temperatures
Fig. 4 The optical texture of 3c by POM (a the optical texture at 108 °C during heating; b the optical
texture at 117 °C during cooling)
disappeared gradually, and no peak existed at the end. Similarly, at higher
temperature, the diffraction peak near 6° gradually became a wide dispersion peak
from a sharp peak. These indeed meant that the phase transition was altered from
smectic phase to isotropic phase.
The textures of target compound 3c observed with POM are shown in Fig. 4.
There is a marble texture, which is one of the typical smectic phase textures [38].
123

Synthesis and characterization of biphenyl liquid
2519
A marble texture with fluidity and bright colors could be observed during heating
(Fig. 4a) and cooling (Fig. 4b). The results are consistent with those tested by DSC
and XRD.
Conclusion
In summary, a series of N-[5-alkoxy-2(5H)-furanonyl] amino acid 40-hexyloxybi-
phenyl esters have been synthesized as designed. The DSC, XRD, and POM results
indicated that most of them were mesomorphic phase liquid crystal molecules. The
new compounds with bornyl moiety were more likely to appear as mesomorphic
phase than those with the menthyl unit. And the introduction of hexyloxy into the
biphenyl esters to improve the liquid crystal performance was successful. These
researches provide a basis for the further application of 2(5H)-furanone compounds
in liquid crystal materials.
Experimental
General
Infrared spectra were recorded on a Bruker Vector 33 FT-IR instrument by the
liquid film method in the absorption range 4,000–400 cm-1. 1H NMR spectra were
obtained in CDCl3 on a Varian DRX-400 MHz spectrometer and tetramethylsilane
(TMS) was used as internal standard. Elemental analysis was performed with a
Thermo Flashea TM 112 elemental analyzer. Mass spectra (MS) were recorded on a
Thermo LCQ DECA XP MAX mass spectrometer.
Differential scanning calorimetry was performed with Perkin-Elmer DSC7
thermal analyzer at a heating rate of 10 °C min-1 under a nitrogen atmosphere
(flow velocity 20 mL min-1). X-ray diffraction was recorded on a Bruker D8
ADVANCE X-ray diffractometer using CuKa radiation with a wavelength of
1.5418 9 10-10 m, and scanning range 2h = 5–50° at a scanning speed of 0.03° at
5 s per step. The optical textures were recorded on a Nikon ECLIPSE polarization
optical microscope equipped with a heating and cooling stage.
All reagents and solvents were commercially available and used as received.
Using furfural, natural L-menthol, L-borneol, and amino acids as starting materials,
the intermediate N-[5-alkoxy-2(5H)-furanonyl] amino acids 1a–1p were prepared
according to the literature [31, 34, 39–41]. 40-Hexyloxybiphenyl-4-ol 2 was also
self-made and according to the literature [42, 43], and its structure characterization
data were consistent with the reported [11, 42, 43].
Typical procedure for synthesis of target compounds 3a–3p
A flame-dried 50-mL round-bottomed flask was charged with 1 (0.2 mmol), and
DCC (0.2 mmol) in dried CH2Cl2 (20 mL), the mixture was stirred for 0.5 h under
reflux, then, 2 (0.2 mmol) in dried CH2Cl2 (5 mL) was dropwise added into the
123

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S.-H. Luo et al.
mixture in half an hour. After that, DMAP (0.24 mmol) was added. The reaction
was stirred for 72 h under reflux. Then, the resulting mixture was extracted with
water (20 mL 9 2). The organic layers were dried with magnesium sulfate, and
concentrated under vacuum to give a crude product, which was purified by column
chromatography on silica gel with gradient eluent of mixtures of petroleum ether
and ethyl acetate to afford the samples 3a–3p for analysis.
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-ylamino)-
4-methylpentanoate (3a)
Yellowish viscous solid, yield 44 %; 1H NMR (400 MHz, CDCl3-TMS)
d: 0.86–1.09 (18H, m, CH3-12, CH3-14, CH3-15, CH3-20, CH3-21, CH3-40),
1.22–1.31 (6H, m, CH2-8, CH2-9, CH2-38), 1.33–1.40 (5H, m, CH-19, CH2-37,
CH2-39), 1.67–1.88 (6H, m, CH2-11, CH2-18, CH2-36), 2.22–2.33 (1H, m, CH-10),
3.97–4.02 (3H, m, CH-6, CH2-35), 4.90 (1H, s, NH-16), 5.35 (1H, t, J = 3.6 Hz,
CH-17), 5.75 (1H, s, CH-5), 6.97 (2H, d, J = 9.2 Hz, ArH-31,33), 7.15 (2H, d,
J = 8.2 Hz, ArH-24,26), 7.43 (2H, d, J = 9.2 Hz, ArH-30,32), 7.57 (2H, d,
J = 8.4 Hz, ArH-25,27); IR (Film) m: 3,352, 3,071, 3,036, 2,955, 2,924, 2,855,
1751, 1643, 1609, 1462, 1250, 1130, 957, 818, 567; ESI-MS m/z (%): 720
([M ? Na]?, 100.0); Anal. Calcd for C38H50BrNO6: C 65.51, H 7.23, N 2.01,
found: C 65.29, H 7.02, N 1.89.
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-ylamino)-
3-methylbutanoate (3b)
Yellowish viscous solid, yield 55 %; 1H NMR (400 MHz, CDCl3-TMS)
d: 0.81–1.00 (18H, m, CH3-12, CH3-14, CH3-15, CH3-19, CH3-20, CH3-39),
1.23–1.29 (6H, m, CH2-8, CH2-9, CH2-37), 1.32–1.37 (4H, m, CH2-36, CH2-38),
1.65–1.72 (2H, m, CH2-11), 1.76–1.84 (2H, m, CH2-35), 1.87–1.94 (1H, m, CH-18),
2.25–2.31 (1H, m, CH-10), 3.99 (2H, t, J = 6.4 Hz, CH2-34), 4.01–4.07 (1H, m,
CH-6), 4.93 (1H, b, NH-16), 5.37 (1H, d, J = 10.0 Hz, CH-17), 5.74 (1H, s, CH-5),
6.96 (2H, d, J = 8.4 Hz, ArH-30,32), 7.15 (2H, d, J = 8.4 Hz, ArH-23,25), 7.48
(2H, d, J = 8.8 Hz, ArH-29,31), 7.57 (2H, d, J = 8.8 Hz, ArH-24,26); IR (Film) m:
3,379, 3,067, 3,036, 2,955, 2,874, 1,763, 1,651, 1,609, 1,497, 1,470, 1,246, 1,130,
956, 829, 633; ESI-MS m/z (%): 701 ([M ? NH4]?, 4.8); Anal. Calcd for
C37H48BrNO6: C 65.10, H 7.09, N 2.05, Found: C 64.90, H 7.00; N 2.12.
40-Hexyloxybiphenyl-4-yl 6-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-ylamino)hexanoate (3c)
1
Yellowish solid, yield 47 %; H NMR (400 MHz, CDCl3-TMS) d: 0.85 (6H, s,
CH3-14, CH3-15), 0.89–0.93 (6H, m, CH3-12, CH3-40), 1.25–1.38 (8H, m, CH2-8,
CH2-9, CH2-19, CH2-38), 1.43–1.56 (4H, m, CH2-39, CH2-37), 1.64–1.74 (6H, m,
CH2-11, CH2-18, CH2-20), 1.78–1.84 (2H, m, CH2-36), 2.22–2.31 (1H, m, CH-10),
123

Synthesis and characterization of biphenyl liquid
2521
2.61 (2H, t, J = 7.2 Hz, CH2-21), 3.44–3.55 (2H, m, CH2-17), 3.94–4.01 (3H, m,
CH-6, CH2-35), 4.92 (1H, s, NH-16), 5.73 (2H, s, CH-5), 6.96 (2H, d, J = 8.8 Hz,
ArH-31,33), 7.11 (2H, d, J = 8.4 Hz, ArH-24,26), 7.48 (2H, d, J = 8.8 Hz, ArH-
30,32), 7.54 (2H, d, J = 8.8 Hz, ArH-25,27); 13C NMR (100 MHz, CDCl3-TMS) d:
14.0 (C-12), 14.1 (C-40), 18.6 (C-14), 19.6 (C-15), 22.6 (C-39), 24.4 (C-20), 25.7
(C-37), 25.9 (C-19), 26.6 (C-9), 28.0 (C-8), 29.7 (C-36), 30.4 (C-18), 31.6 (C-38),
34.0 (C-21), 37.1 (C-11), 43.9 (C-17), 44.9 (C-10), 47.6 (C-7), 49.5 (C-13), 68.1
(C-35), 77.3 (C-6), 87.6 (C-3), 99.1 (C-5), 114.8 (C-31, C-33), 121.7 (C-24, C-26),
127.7 (C-25, C-27), 128.1 (C-30, C-32), 132.6 (C-29), 138.7 (C-28), 149.4 (C-23),
154.9 (C-34), 158.8 (C-4), 167.5 (C-2), 172.0 (C-22); IR (Film) m: 3,348, 3,040,
2,928, 2,866, 1,759, 1,632, 1,524, 1,497, 1,462, 1,207, 1,138, 937, 825, 613; ESI-
MS m/z (%): 698 ([M ? H]?, 21.0), 720 ([M ? Na]?, 16.0); Anal. Calcd for
C38H50BrNO6: C 65.51, H 7.23, N 2.01, found: C 65.32, H 7.02, N 1.89.
40-Hexyloxybiphenyl-4-yl 2-(((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-yl)-
N-methylamino)acetate (3d)
Yellowish solid, yield 31 %; 1H NMR (400 MHz, CDCl3-TMS) d: 0.85–0.92 (12H,
m, CH3-14, CH3-15, CH3-12, CH3-37), 1.24–1.31 (6H, m, CH2-8, CH2-9, CH2-35),
1.33–1.37 (4H, m, CH2-34, CH2-36), 1.67–1.86 (4H, m, CH2-11, CH2-33),
2.21–2.31 (1H, m, CH-10), 3.29 (3H, s, CH3-17), 3.94–3.97 (1H, m, CH-6), 3.99
(2H, t, J = 6.4 Hz, CH2-32), 4.48–4.85 (2H, dd, J1 = 11.2 Hz, J2 = 18.4 Hz, CH2-
18), 5.82 (1H, s, CH-5), 6.96 (2H, d, J = 7.6 Hz, ArH-29,30), 7.18 (2H, d,
J = 8.4 Hz, ArH-21,22), 7.48 (2H, d, J = 8.4 Hz, ArH-27,28), 7.56 (2H, d,
J = 8.8 Hz, ArH-23,24); IR (Film) m: 3,318, 3,036, 2,928, 2,865, 1,751, 1,624,
1,574, 1,524, 1,493, 1,199, 1,169, 961, 826, 637; ESI-MS m/z (%): 694 ([M ? K]?,
100.0); Anal. Calcd for C35H44BrNO6: C 64.22, H 6.77, N 2.14, found: C 64.02, H
6.57, N 2.04.
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-ylamino)-
3-phenylpropanoate (3e)
Yellowish viscous solid, yield 38 %; 1H NMR (400 MHz, CDCl3-TMS)
d: 0.73–0.93 (12H, m, CH3-12, CH3-14, CH3-15, CH3-43), 1.27–1.31 (6H, m,
CH2-8, CH2-9, CH2-42), 1.33–1.35 (2H, m, CH2-41), 1.42–1.48 (2H, m, CH2-40),
1.65–1.71 (2H, m, CH2-11), 1.76–1.84 (2H, m, CH2-39), 2.22–2.33 (1H, m, CH-10),
3.11–3.31 (2H, dd, J1 = 14.4 Hz, J2 = 14.4 Hz, CH2-18), 3.99 (2H, t, J = 6.4 Hz,
CH2-38), 4.09–4.15 (2H, m, CH-6, CH-17), 5.08 (1H, s, NH-16), 5.53 (1H, s, CH-5),
6.96 (2H, d, J = 8.4 Hz, ArH-35,36), 7.15 (2H, d, J = 8.4 Hz, ArH-27,28),
7.18–7.26 (4H, m, ArH-20,21,23,24), 7.30–7.39 (1H, m, ArH-22), 7.48 (2H, d,
J = 8.4 Hz, ArH-33,34), 7.56 (2H, d, J = 8.4 Hz, ArH-29,30); IR (Film) m: 3,364,
3,036, 2,924, 2,865, 1,751, 1,636, 1,609, 1,497, 1,450, 1,204, 1,165, 972, 802, 630;
ESI-MS m/z (%): 751 ([M ? NH4]?, 8.3); Anal. Calcd for C41H48BrNO6: C 67.39,
H 6.62, N 1.92, found: C 67.23, H 6.52, N 1.77.
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40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-ylamino)-2-
phenylacetate (3f)
Yellowish viscous solid, yield 31 %; 1H NMR (400 MHz, CDCl3-TMS)
d: 0.82–0.93 (12H, m, CH3-12, CH3-14, CH3-15, CH3-42), 1.24–1.28 (6H, m,
CH2-8, CH2-9, CH2-41), 1.32–1.35 (2H, m, CH2-40), 1.42–1.49 (2H, m, CH2-39),
1.64–1.67 (2H, m, CH2-11), 1.75–1.83 (2H, m, CH2-38), 2.19–2.28 (1H, m, CH-10),
3.96–4.02 (3H, m, CH-6, CH2-37), 5.19–5.21 (1H, m, CH-17), 6.16–6.25 (1H, m,
CH-5, NH-16), 6.93 (2H, d, J = 8.4 Hz, ArH-34,35), 7.17 (2H, d, J = 8.4 Hz,
ArH-26,27), 7.31 (2H, d, J = 8.4 Hz, ArH-32,33), 7.36–7.42 (5H, m, ArH-19,20,
21,22,23), 7.50 (2H, d, J = 8.8 Hz, ArH-28,29); IR (Film) m: 3,391, 3,063, 3,036,
2,928, 2,855, 1,755, 1,674, 1,609, 1,524, 1,450, 1,207, 1,165, 972, 829, 644; ESI-
MS m/z (%): 718 ([M ? H]?, 9.4); Anal. Calcd for C40H46BrNO6: C 67.03, H 6.47,
N 1.95, found: C 67.00, H 6.27, N 1.83.
40-Hexyloxybiphenyl-4-yl 4-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-ylamino)butanoate (3g)
1
Yellowish solid, yield 31 %; H NMR (400 MHz, CDCl3-TMS) d: 0.84 (6H, s,
CH3-14, CH3-15), 0.88–0.93 (6H, m, CH3-12, CH3-38), 1.24–1.28 (6H, m, CH2-8,
CH2-9, CH2-36), 1.32–1.36 (2H, m, CH2-37), 1.41–1.49 (2H, m, CH2-35), 1.61–1.64
(2H, m, CH2-11), 1.76–1.84 (2H, m, CH2-34), 2.06–2.14 (2H, m, CH2-18),
2.23–2.30 (1H, m, CH-10), 2.69–2.77 (2H, m, CH2-19), 3.58–3.68 (2H, m, CH2-17),
3.96–4.03 (3H, m, CH-6, CH2-33), 5.13 (1H, s, NH-16), 5.75 (1H, s, CH-5), 6.96
(2H, d, J = 8.8 Hz, ArH-29,31), 7.12 (2H, d, J = 8.4 Hz, ArH-22,24), 7.47 (2H, d,
J = 8.4 Hz, ArH-28,30), 7.54 (2H, d, J = 8.4 Hz, ArH-23,25); IR (Film) m: 3,318,
3,036, 2,928, 2,865, 1,751, 1,639, 1,558, 1,528, 1,497, 1,204, 1,134, 949, 829, 579;
ESI-MS m/z (%): 692 ([M ? Na]?, 25.0); Anal. Calcd for C35H44BrNO6: C 64.66,
H 6.93, N 2.09, found: C 64.56, H 6.87, N 2.00.
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-ylamino)acetate (3h)
Yellowish liquid, yield 36 %; 1H NMR (400 MHz, CDCl3-TMS) d: 0.83–1.11
(12H, m, CH3-12, CH3-14, CH3-15, CH3-36), 1.25–1.34 (8H, m, CH2-8, CH2-9,
CH2-34, CH2-35), 1.57–1.64 (4H, m, CH2-11, CH2-33), 1.73–1.87 (2H, m, CH2-32),
2.22–2.36 (1H, m, CH-10), 3.65–4.24 (5H, m, CH-6, CH2-17, CH2-31), 5.35 (1H, s,
NH), 5.58 (1H, s, CH-5), 6.87–7.16 (4H, m, ArH-20,21,28,29), 7.30–7.61 (4H, m,
ArH-22,23,26,27); IR (Film) m: 3,360, 3,036, 2,924, 2,851, 1,736, 1,655, 1,609,
1,493, 1,466, 1,261, 1,166, 1,018, 803, 664; ESI-MS m/z (%): 642 ([M ? H]?, 6.4);
Anal. Calcd for C34H42BrNO6: C 63.75, H 6.61, N 2.19, found: C 63.55, H 6.41, N
2.28.
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2523
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-2-((1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy)-5-oxo-2,5-dihydrofuran-3-ylamino)-4-methylpentanoate (3i)
1
White viscous solid, yield 32 %, H NMR (400 MHz, CDCl3-TMS) d: 0.82–1.00
(12H, m, CH3-12, CH3-14, CH3-15, CH3-40), 1.25–1.29 (13H, m, CH-8, CH2-9,
CH-11, CH-13, CH3-20, CH3-21, CH2-38), 1.33–1.38 (4H, m, CH2-37, CH2-39),
1.57–1.59 (5H, m, CH2-10, CH2-18, CH-19), 1.76–1.84 (2H, m, CH2-36), 2.01–2.25
(2H, m, CH2-7), 3.96–4.10 (3H, m, CH-6, CH2-35), 4.89 (1H, b, NH), 5.25–5.44
(2H, m, CH-5, CH-17), 6.88 (2H, d, J = 8.0 Hz, ArH-31,33), 6.94 (2H, d,
J = 8.4 Hz, ArH-24,26), 7.41–7.46 (4H, m, ArH-30,32,25,27); IR (Film) m: 3,391,
3,005, 2,920, 2,851, 1,732, 1,643, 1,500, 1,466, 1,250, 1,184, 968, 818, 644; ESI-
MS m/z (%): 722 ([M ? Na]?, 17.0); Anal. Calcd for C38H52BrNO6: C 65.32, H
7.50, N 2.00, found: C 65.22, H 7.43, N 2.02.
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-2-((1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy)-5-oxo-2,5-dihydrofuran-3-ylamino)-3-methylbutanoate (3j)
White viscous solid, yield 32 %; 1H NMR (400 MHz, CDCl3-TMS) d: 0.60 (3H, d,
J = 6.8 Hz, CH3-12), 0.77–0.98 (16H, m, CH-13, CH3-14, CH3-15, CH3-19, CH3-
20, CH3-39), 1.05–1.15 (2H, m, CH2-9), 1.25–1.36 (8H, m, CH-8, CH-11, CH2-36,
CH2-37, CH2-38), 1.59–1.62 (2H, m, CH2-10), 1.78–1.85 (3H, m, CH-18, CH2-35),
2.02–2.23 (2H, m, CH2-7), 3.45–3.51 (1H, m, CH-6), 3.90–4.10 (3H, m, CH-17,
CH2-34), 5.35 (1H, b, NH), 5.92 (1H, s, CH-5), 6.98 (2H, d, J = 8.4 Hz, ArH-
30,32), 7.18 (2H, d, J = 8.4 Hz, ArH-23,25), 7.50 (2H, d, J = 8.0 Hz, ArH-29,31),
7.57 (2H, d, J = 8.4 Hz, ArH-24,26); IR (Film) m: 3,364, 3,040, 2,924, 2,855, 1,782,
1,659, 1,609, 1,466, 1,246, 1,180, 949, 822, 606; ESI-MS m/z (%): 686 ([M ? H]?,
15.0); Anal. Calcd for C38H50BrNO6: C 64.90, H 7.36, N 2.05, found: C 64.75, H
7.26, N 2.10.
40-Hexyloxybiphenyl-4-yl 6-((S)-4-bromo-2-((1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy)-5-oxo-2,5-dihydrofuran-3-ylamino)hexanoate (3k)
1
Yellowish solid, yield 30 %; H NMR (400 MHz, CDCl3-TMS) d: 0.79 (3H, d,
J = 7.2 Hz, CH3-12), 0.83–0.93 (10H, m, CH-13, CH3-14, CH3-15, CH3-39),
0.95–1.04 (2H, m, CH2-9), 1.32–1.51 (10H, m, CH-8, CH-11, CH2-18, CH2-36,
CH2-37, CH2-38), 1.62–1.69 (6H, m, CH2-10, CH2-17, CH2-19), 1.76–1.90 (2H, m,
CH2-35), 2.10–2.25 (2H, m, CH2-7), 2.60 (2H, t, J = 7.2 Hz, CH2-20), 3.43–3.57
(3H, m, CH-6, CH2-16), 3.97 (2H, t, J = 6.8 Hz, CH2-34), 4.77 (1H, s, NH), 5.71
(1H, s, CH-5), 6.94 (2H, d, J = 8.8 Hz, ArH-30,32), 7.09 (2H, d, J = 8.8 Hz, ArH-
23,25), 7.46 (2H, d, J = 8.8 Hz, ArH-29,31), 7.52 (2H, d, J = 8.4 Hz, ArH-24,26);
13C NMR (100 MHz, CDCl3-TMS) d: 14.0 (C-39), 15.9 (C-12), 21.0 (C-10), 22.1
(C-14), 22.6 (C-15), 22.8 (C-38), 24.3 (C-19), 24.9 (C-36), 25.7 (C-11), 25.8 (C-18),
29.2 (C-35), 30.3 (C-17), 31.5 (C-13), 31.6 (C-37), 33.9 (C-20), 34.0 (C-9), 42.4 (C-
7), 43.6 (C-16), 48.1 (C-8), 68.1 (C-34), 77.2 (C-6), 81.9 (C-3), 98.6 (C-5), 114.8
(C-30, C-32), 121.6 (C-23, C-25), 127.6 (C-24, C-26), 128.0 (C-29, C-31), 132.5
(C-28), 138.7 (C-27), 149.4 (C-22), 156.8 (C-33), 158.8 (C-4), 167.7 (C-2), 171.9
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(C-21); IR (Film) m: 3,321, 3,032, 2,924, 2,855, 1,732, 1,651, 1,574, 1,497, 1,462,
1,204, 1,126, 937, 826, 640; ESI-MS m/z (%): 722 ([M ? Na]?, 12.0); Anal. Calcd
for C38H52BrNO6: C 65.32, H 7.50, N 2.00, found: C 65.12, H 7.33, N 2.08.
40-Hexyloxybiphenyl-4-yl 2-(((S)-4-bromo-2-((1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy)-5-oxo-2,5-dihydrofuran-3-yl)-N-methylamino)acetate (3l)
White viscous solid, yield 31 %; 1H NMR (400 MHz, CDCl3-TMS) d: 0.79 (3H, d,
J = 6.8 Hz, CH3-12), 0.86–0.96 (10H, m, CH-13, CH3-14, CH3-15, CH3-37),
0.98–1.14 (2H, m, CH2-9), 1.31–1.40 (6H, m, CH-8, CH-11, CH2-35, CH2-36),
1.43–1.50 (2H, m, CH2-34), 1.64–1.70 (2H, m, CH2-10), 1.76–1.84 (2H, m, CH2-
33), 2.19–2.27 (2H, m, CH2-7), 3.26 (3H, s, CH3-17), 3.58–3.66 (1H, ddd,
J = 4.4 Hz, J = 4.0 Hz, J = 4.4 Hz, CH-6), 3.99 (2H, t, J = 6.4 Hz, CH2-32),
4.39–4.45 (2H, dd, J1 = 16.0 Hz, J2 = 18.4 Hz, CH2-18), 5.90 (1H, s, CH-5), 6.97
(2H, d, J = 8.8 Hz, ArH-29,30), 7.17 (2H, d, J = 8.4 Hz, ArH-21,22), 7.48 (2H, d,
J = 8.8 Hz, ArH-27,28), 7.56 (2H, d, J = 8.8 Hz, ArH-23,24); IR (Film) m: 3,345,
3,040, 2,928, 2,866, 1,757, 1,632, 1,524, 1,497, 1,466, 1,246, 1,109, 957, 826, 640;
ESI-MS m/z (%): 680 ([M ? Na]?, 19.0); Anal. Calcd for C35H46BrNO6: C 64.02,
H 7.06, N 2.17, found: C 64.00, H 7.20, N 2.11.
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-2-((1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy)-5-oxo-2,5-dihydrofuran-3-ylamino)-3-phenylpropanoate
(3m)
1
Yellowish liquid, yield 29 %; H NMR (400 MHz, CDCl3-TMS) d: 0.85 (3H, d,
J = 7.2 Hz, CH3-12), 0.91–0.98 (10H, m, CH-13, CH3-14, CH3-15, CH3-43),
1.00–1.09 (2H, m, CH2-9), 1.32–1.40 (6H, m, CH-8, CH-11, CH2-41, CH2-42),
1.43–1.49 (2H, m, CH2-40), 1.67–1.75 (2H, m, CH2-10), 1.77–1.84 (2H, m, CH2-
39), 2.00–2.11 (2H, m, CH2-7), 3.52–3.68 (1H, ddd, J1 = 3.6 Hz, J2 = 4.0 Hz,
J3 = 4.4 Hz, CH-6), 3.93–4.01 (2H, m, CH2-18), 4.31 (2H, t, J = 6.4 Hz, CH2-38),
5.34–5.97 (3H, m, CH-5, NH, CH-17), 6.88 (2H, d, J = 8.0 Hz, ArH-33,34), 6.94
(2H, d, J = 8.0 Hz, ArH-27,28), 7.37–7.46 (5H, m, ArH-20,21,22,23,24), 7.52–7.56
(2H, m, ArH-33,34), 7.71–7.75 (2H, m, ArH-29,30); IR (Film) m: 3,372, 3,067,
3,032, 2,932, 2,870, 1,728, 1,651, 1,501, 1,454, 1,277, 1,173, 953, 822, 567; ESI-
MS m/z (%): 734 ([M ? H]?, 10.0); Anal. Calcd for C41H50BrNO6: C 67.20, H
6.88, N 1.91, found: C 67.01, H 6.78, N 1.82.
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-2-((1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy)-5-oxo-2,5-dihydrofuran-3-ylamino)-2-phenylacetate (3n)
Yellowish solid, yield 34 %; 1H NMR (400 MHz, CDCl3-TMS) d: 0.79–0.97 (15H,
m, CH2-9, CH3-12, CH-13, CH3-14, CH3-15, CH3-42), 1.25–1.36 (8H, m, CH-8,
CH-11, CH2-39, CH2-40, CH2-41), 1.67–1.74 (2H, m, CH2-10), 1.76–1.84 (2H, m,
CH2-38), 2.17–2.33 (2H, m, CH2-7), 3.52–3.62 (1H, m, CH-6), 4.31 (2H, t,
J = 6.4 Hz, CH2-37), 5.57–5.90 (3H, m, CH-5, NH, CH-17), 6.88 (2H, d,
J = 8.0 Hz, ArH-30,32), 6.94 (2H, d, J = 8.4 Hz, ArH-26,27), 7.39–7.46 (5H, m,
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Synthesis and characterization of biphenyl liquid
2525
ArH-19, 20,21,22,23), 7.53–7.56 (2H, m, ArH-29,31), 7.70–7.75 (2H, m, ArH-
28,29); IR (Film) m: 3,372, 3,067, 3,032, 2,932, 2,870, 1,728, 1,651, 1,501, 1,454,
1,277, 1,173, 953, 822, 567; ESI-MS m/z (%): 720 ([M ? H]?, 5.0); Anal. Calcd for
C40H48BrNO6: C 66.85, H 6.73, N 1.95, found: C 66.78, H 6.59, N 1.79.
40-Hexyloxybiphenyl-4-yl 4-((S)-4-bromo-2-((1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy)-5-oxo-2,5-dihydrofuran-3-ylamino)butanoate (3o)
Yellowish viscous solid, yield 30 %; 1H NMR (400 MHz, CDCl3-TMS)
d: 0.77–1.16 (15H, m, CH2-9, CH3-12, CH-13, CH3-14, CH3-15, CH3-38),
1.28–1.34 (4H, m, CH2-36, CH2-37), 1.39–1.43 (2H, m, CH-8, CH-11), 1.57–1.60
(2H, m, CH2-35), 1.73–1.82 (4H, m, CH2-10, CH2-34), 1.92–2.07 (4H, m, CH2-7,
CH2-18), 2.20–2.86 (2H, m, CH2-19), 3.47–3.64 (2H, m, CH2-17), 3.97–4.09 (3H,
m, CH-6, CH2-33), 4.68–5.35 (2H, m, CH-5, NH), 6.95 (2H, d, J = 7.6 Hz, ArH-
29,31), 7.17 (2H, d, J = 7.6 Hz, ArH-22,24), 7.48 (2H, d, J = 8.4 Hz, ArH-28,30),
7.51 (2H, d, J = 8.4 Hz, ArH-23,25); IR (Film) m: 3,333, 3,005, 2,924, 2,851, 1,705,
1,609, 1,535, 1,497, 1,450, 1,231, 1,173, 964, 822, 644; ESI-MS m/z (%): 694
([M ? Na]?, 7.3); Anal. Calcd for C36H48BrNO6: C 64.47, H 7.21, N 2.09, found: C
64.35, H 7.15, N 2.00.
40-Hexyloxybiphenyl-4-yl 2-((S)-4-bromo-2-((1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy)-5-oxo-2,5-dihydrofuran-3-ylamino)acetate (3p)
1
Yellowish viscous solid, yield 32 %; H NMR (400 MHz, CDCl3-TMS) d: 0.85
(3H, d, J = 6.8 Hz, CH3-12), 0.91–0.97 (10H, m, CH-13, CH3-14, CH3-15, CH3-
36), 1.01–1.10 (2H, m, CH2-9), 1.28–1.34 (8H, m, CH-8, CH-11, CH2-33, CH2-34,
CH2-35), 1.61–1.68 (2H, m, CH2-10), 1.78–1.82 (2H, m, CH2-32), 2.14–2.27 (2H,
m, CH2-7), 3.54–3.61 (1H, ddd, J1 = 4.0 Hz, J2 = 4.0 Hz, J3 = 4.4 Hz, CH-6),
4.26–4.36 (4H, m, CH2-17, CH2-31), 5.33 (1H, s, NH), 5.73 (1H, s, CH-5),
6.87–7.15 (4H, m, ArH-20,21,28,29), 7.35–7.55 (4H, m, ArH-22,23,26,27); IR
(Film) m: 3,368, 3,032, 2,928, 2,855, 1,748, 1,655, 1,524, 1,458, 1,204, 1,126, 941,
822, 598; ESI-MS m/z (%): 666 ([M ? Na]?, 20.0); Anal. Calcd for C34H44BrNO6:
C 63.55, H 6.90, N 2.18, found: C 63.39, H 6.78, N 2.06.
Acknowledgments We are grateful to the National Natural Science Foundation of China
(No. 20772035), the Third Talents Special Funds of Guangdong Higher Education (No. Guangdong-
Finance-Education [2011]431) and the Natural Science Foundation of Guangdong Province
(No. S2011010001556) for financial support.
References
1. J. Milette, S. Relaix, C. Lavigne, V. Toader, S.J. Cowling, I.M. Saez, R.B. Lennox, J.W. Goodby, L.
Reven, Soft Matter 8, 2593 (2012)
2. K. Kishikawa, H. Itoh, S. Akiyama, T. Kobayashi, S. Kohmoto, J. Mater. Chem. 22, 8484 (2012)
3. J.-G. Zhang, J.-Y. Su, Y.-P. Ma, H.-X. Guo, J. Phys. Chem. B 116, 2075 (2012)
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