A phase-dependent photoluminescent discotic liquid crystal bearing a graphdiyne substructure

Article abstract of DOI:10.1039/d0cc05959e

In recent years, graphdiyne and its derivatives with fascinating electro-optic properties have attracted tremendous scientific attention. Here we design and synthesize a graphdiyne-derived discotic liquid crystal material by decorating six wedge-shaped 3,

Full text of DOI:10.1039/d0cc05959e

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Phase-Dependent Photoluminescent Discotic Liquid Crystal
Bearing Graphdiyne Substructure
Received 00th September 2020,
a
a
a
a
a
a
Accepted 00th September 2020
DOI: 10.1039/x0xx00000x
www.rsc.org/
Zhen Yu, Xu-Man Chen, Zhi-Yang Liu, Meng Wang, Shuai Huang, and Hong Yang *
In recent years, graphdiyne and its derivatives with fascinating molecule displaying particularly interesting self-assembly and
1
1,12
electro-optic properties have attracted tremendous scientific optoelectronic properties.
In addition, its shape-persistent
attention. Here we design and synthesize a graphdiyne-derived macrocyclic derivatives have exhibited many fascinating
discotic liquid crystal material by decorating six wedge-shaped characteristics in the fields of host-guest chemistry,
3
,4,5-tris(dodecyloxy)benzoate groups on the fundamental supramolecular assembly, and crystalline materials. For
structural unit of graphdiyne, dehydrotribenzo[18]annulene core. example, multipore covalent organic framework (COF)
This graphdiyne-derived liquid crystal material exhibits cubic materials constructed by DBA monomer units in the solid state
phase and hexagonal columnar phase at varied temperatures. were highly fluorescent because of the coplanar arrangement
1
3–15
Most interestingly, this molecule displays a tunable phase- of DBA units.
dependent photoluminescence behavior. Under the irradiation of investigated for self-assembly at the liquid-solid interface by
65 nm wavelength ultraviolet light, the luminescent material scanning tunneling microscope, which displayed highly
emits pale blue, green and azure light in the cubic, hexagonal ordered 2D molecular networks with alkyl chain interdigitation
A series of DBA[18] derivatives have been
3
1
6
columnar and isotropic phases respectively. This graphdiyne- and lamella patterns.
Apparently, efficient spatial
derived discotic liquid crystal with excellent optical characteristics arrangements of the π-electron-conjugated molecules into
might have application potentials in organic optoelectronic well-defined nanometer-scaled structures of functional
functional materials and devices.
materials would dramatically enhance their inherent
properties. Liquid-crystalline ordering offers the possibility of
constructing well-organized π-conjugated materials.
Graphynes (GYs), a series of two-dimensional (2D) sp-sp2
hybridized carbon allotropes, display fascinating electro-optic
properties, such as high carrier mobility, excellent native band
gap, anisotropic optical property, which have attracted
tremendous scientific attention in recent years. As the most
representative member of GY family, graphdiyne (GDY, Figure
17–19
1
–3
1
) with a 2D layered network structure formed by two
conjugated triple bonds (−C≡C−C≡C−) connecting aromatic
carbon rings,4 exhibits great advantages in photo-related and
electrochemical applications because of its unique atom
–7
2
arrangement, coexistence of sp- and sp -hybridizations and
8
–10
extended π-conjugated system.
As schematically illustrated in Figure 1, the fundamental
structural unit of GDY can be identified as liquid crystal molecule reported in this work.
Figure 1 The molecular structures of graphdiyne and the graphdiyne-derived
3
dehydrotribenzo[18]annulene (DBA[18]) with a C -symmetric
axis. DBA[18] is a planar shape-persistent macrocyclic
As it is well known, liquid crystals (LCs) are an exceptional
class of engineered molecular materials that can effectively
control the self-assembly of π-conjugated units to obtain
2
0,21
functional architectures.
In particular, discotic LCs are able
a
Jiangsu Province Hi-Tech Key Laboratory for Bio-medical Research, State Key
Laboratory of Bioelectronics, Institute of Advanced Materials, School of Chemistry
to spontaneously stack π-conjugated molecules into highly
and Chemical Engineering, Southeast University, Nanjing 211189, Jiangsu, China. E- ordered periodic columns and then aggregate into 2D lattices
mail: yangh@seu.edu.cn
Electronic Supplementary Information (ESI) available: Experimental section and
through non-covalent interactions that can provide significant
†
supplementary figures. See DOI:
nanochannels for effective charge mobility, ion transportation,
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separation, filtration, adsorption and so on.22,23 However to 3,4,5-tris(dodecyloxy)benzoyl chloride (10). TVhieweArtidclee sOinrleinde
our surprise, the incorporation of GDY substructure DBA[18] discotic molecule GDYLC12 (11) was DsuOcI:c1e0s.1s0fu39ll/yD0pCrCe0p5a9r5e9dE
into discotic LCs has never been reported in literature before.
through an esterification reaction of the compound 7 with acyl
Here, we designed and synthesized a discotic LC material chloride 10 in presence of trimethylamine at 40 °C.
named as GDYLC12) derived from the planar π-conjugated
(
DBA[18]-core macrocyclic molecule, as shown in Figure 1. To
arrange the DBA[18] core into a discotic LC, six wedge-shaped
3
,4,5-tris(dodecyloxy)benzoate groups bearing 18 terminal
alkoxy side chains were introduced in the building block core.
The synthesis, mesomorphic property, optical behavior and
electrochemical performances of GDYLC12 are investigated
and described in this manuscript.
Figure 2. (a) POM image of GDYLC12 recorded upon heating process at room
2
temperature. (b) DSC thermogram of GDYLC12 recorded under N atmosphere
with a heating/cooling scan rate of 10 °C /min. SAXS−WAXS patterns of GDYLC12
recorded on (c) heating and (d) cooling processes.
The thermotropic liquid crystalline properties and
mesomorphic structure of DBA[18]-core molecule GDYLC12
were investigated by utilization of polarized optical microscopy
(
POM), differential scanning calorimetry (DSC), and
temperature-varied small- and wide-angle X-ray scattering
SAXS−WAXS) measurements. Thermal stability of GDYLC12
was characterized using thermogravimetric analysis (TGA)
under N atmosphere, the initial thermal decomposition
temperatures (T , 5 % weight loss) of GDYLC12 was ca. 341 °C
Figure S25), which demonstrated a good thermal stability over
Scheme 1. Synthetic route of the dodecadehydrotribenzo[18]annulene-core
(
discotic liquid crystal GDYLC12.
2
The synthetic route of the DBA[18]-core discotic LC molecule
GDYLC12 is schematically illustrated in Scheme 1. The
production of the target GDYLC12 started with a diiodination
of 1,2-dimethoxybenzene with iodine and periodic acid in
d
(
a broad temperature range. Under POM observation (Figure
2a), GDYLC12 exhibited a room-temperature dendritic-like
growth aggregates upon cooling from the isotropic melt, which
was the characteristic of thermotropic columnar mesophase.
The X-ray diffractogram of GDYLC12 showed three reflections
in the small-angle region at 15 °C (Figure 2d), which consisted
of a sharp scattering peak at d-spacing of 35.2 Å, and two weak
peaks at d-spacing of 20.2 Å, 17.5 Å. The above peaks were
assigned to 100, 110 and 200 signals respectively, with a
relative d-spacing ratio of 1: √3: 2, which revealed the
1
3
methanol to provide 1,2-diiodo-4,5-dimethoxybenzene (1),
which was further engaged in a demethylation reaction
through BBr activation to yield 1,2-dihydroxy-4,5-
a
3
diiodobenzene (2). Protection of the hydroxyl groups of
compound 2 by using 3,4-dihydro-2H-pyran provided the
intermediate 3. Palladium-catalyzed cross-coupling of the
resulting diiodide 3 with (trimethylsilyl)acetylene (TMSA)
proceeded smoothly at 50 °C to yield silyl-protected diethynyl
arene 4, which was directly subjected to a deprotection of the
trimethylsilyl group, affording the free diyne 5. In order to
construct the DBA[18] framework, the key intermediate 6 was
h
characteristic reflections of hexagonal columnar (Col ) phase,
with a lattice constant a = 40.6 Å. Furthermore, the liquid like
packing of peripheral aliphatic alkoxy chains were confirmed
by a broad halo at 4.4 Å in the wide-angle region. When
GDYLC12 was cooled to below −10 °C, the birefringent texture
vanished as shown in Figure S31 and Video S1, implying that an
optically isotropic cubic phase might appear at low
synthesized in
a
modest yield (22 %) through
a
1
3
cyclotrimerization reaction of the compound 5 catalyzed by
cupric acetate monohydrate and pyridine in methanol and
ether at 60 °C. Deprotection of the tetrahydropyranyl group of
the compound 6 provided the DBA[18]-core 7. A substitution
reaction of methyl gallate with 1-bromododecane and
2
4–28
temperature.
Moreover, the X-ray diffractogram was
significantly different, a sharp scattering peak at 35.5 Å and
four weak peaks at 24.3 Å, 20.5 Å, 17.7 Å, 15.8 Å were
observed at −10 °C. A relative d-spacing ratio of 1: √2: √3: √4:
potassium
tris(dodecyloxy)methyl benzoate (8), which was then engaged
in hydrolysis reaction to produce 3,4,5-
tris(dodecyloxy)benzoic acid (9) and further transformed into
carbonate
in
DMF
offered
3,4,5-
a
√5, was indexed to the pattern of the cubic (Cub) phase with a
2
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Pm3m lattice.29–32 As illustrated in Figure 2b, the DSC diagram mesophase-regulated molecular stacking struVcietwurAertisc.le OTnlhinee
of GDYLC12 manifested two enantiotropic phase transitions, stacking variation was confirmed by teDmOpI:e1r0a.1t0u3r9e/-Dd0eCpCe0n5d9e59nEt
corresponding to a Cub-to-Col
Col -to-isotropic transition around 42.7 °C upon heating diffraction peaks in the small-angle region (1° ~ 5°) and the
process. On the cooling process, a relatively large hysteresis of obvious diffraction peak shift in the wide-angle region (12° ~
Col -to-isotropic phase transition was observed, which was 17°) in the temperature range from 15 °C to −10 °C (Figure 2d).
attributed to the high viscosity of discotic LC molecule.
proposed packing models for the Cub and Col phases are molecular arrangement alteration during the phase transition
shown in Figure S32. Overall, the above measurement results from Cub phase to Col
confirmed that the GDY-derived discotic mesogen GDYLC12 condensed intracolumnar packing in Col
had a broad range of liquid crystalline phase and could retain unconsolidated stacking of aromatic cores in both the optically
its mesophase even at very low temperature. isotropic Cub phase and the isotropic phase resulted in the
h
transition around −6 °C and a X-ray scattering experiment, which exhibited the varied
h
h
3
3,34
The Hence, the remarkable red shift may be attributed to the
h
3
5–37
h
phase.
Compared with the
phase, the
h
UV-Vis absorbance and fluorescence of the discotic mesogen lesser interchromophoric π‒π interactions, which induced
GDYLC12 were investigated in both solution and spin-coated strong blue-shifted emission. Therefore, the fluorescence color
thin film. As illustrated in Figure 3a, the UV-Vis spectrum of could be tuned via altering the temperature/phase-dependent
GDYLC12 solution showed a short wavelength absorption band molecular stacking structures. Some typical images of
with two peaks at around 317 and 339 nm. This absorption GDYLC12 thin film upon heating from the Cub phase to the
band was ascribed to π−π* transition localized on the DBA[18] isotropic state were provided in Figure 4a. Under UV light of
core. The long wavelength absorption band showed two peaks 365 nm wavelength, the green light emission at 20 °C in the
h
at around 367 nm and 377 nm, which was assigned to n−π* ordered Col columnar phase was in striking contrast to the
transition derived from the alkoxyphenyl fragments. The pale blue emission at −20 °C in the Cub phase and the azure
fluorescence spectrum of GDYLC12 showed an emission band light appeared at 60 °C in the isotropic liquid phase,
centered at 434 nm with a shoulder peak at 422 nm. A large respectively. As expected, the CIE chromaticity diagram
stokes shift of 95 nm was observed for this LC molecule in showed the analogously luminescent color changes of
solution. It should be noted that GDYLC12 emitted a dark blue GDYLC12 thin film at −20 °C, 20 °C and 60 °C (Figure S33).
fluorescence in dilute solution upon excitation at 365 nm UV Overall, a remarkable phase-dependent photoluminescence
light as shown in Figure 3a (inset), the absolute fluorescence behavior of the GDY-derived LC molecule was modulated by
-5
F
quantum yield (Φ ) was ca. 78.7 % (conc. = 1.0 X 10 mol/L). the temperature-regulated intracolumnar stacking variation.
UV-Vis absorption spectra of the spin-coated GDYLC12 thin
film showed a similar curve shape at varied temperatures
(
Figure 3b), although the relative absorbance gradually
increased along with the temperature rising from −20 °C to 60
C.
°
Figure 4. (a) Fluorescence images of GDYLC12 thin film under 365 nm UV
illumination at −20 °C (left), 20 °C (middle) and 60 °C (right) respectively.
Fluorescence spectra (λex = 350 nm) of the spin-coated GDYLC12 thin film from (b)
Figure 3. (a) UV-Vis and fluorescence spectra (λex = 350 nm) collected from
-5
GDYLC12 in chloroform solution (conc. = 1.0 X 10 mol/L) at room temperature.
Inset: fluorescent image of GDYLC12 solution taken under 365 nm UV
illumination. (b) UV-Vis spectra of the spin-coated thin film of GDYLC12
measured at different temperatures. Inset: absorbance at 384 nm of (b).
−20 to 20 °C, and (c) 20 to 60 °C.
The existence of intracolumnar stacking interactions was
Figure 4 depicted temperature-dependent fluorescence
emission of the spin-coated GDYLC12 thin film in three distinct
further confirmed by the corresponding fluorescence decay
profiles, the decay lifetime in solid state about 10.48 ns for
GDYLC12 was found to be higher than that in dilute chloroform
h
states (Cub phase, Col phase and isotropic phase). As
demonstrated in Figure 4b, in the cubic phase below −6 °C, the
maximum emission wavelength appeared at ca. 439 nm and
showed no distinct change as the temperature elevated. Next,
(
ca. 1.78 ns) at room temperature (Figure S35,36). The
restricted intramolecular motions and effective π-electronic
delocalization determined the relatively slow deactivation
process in solid state. In addition, a reduced fluorescence
lifetime in organic solvent may be caused by the non-radiative
deactivation process, which derived from the intramolecular
motion of a flexible structural component.
h
in the Col phase centered at 20 °C, the emission spectrum had
a significant red shift (λmax = 499 nm) compared to that in the
Cub phase. As the temperature was elevated further to the
isotropic liquid phase (above 42.7 °C), the emission maximum
of GDYLC12 was blue-shifted and appeared at 440 nm (Figure
Electrochemical properties of GDYLC12 were investigated by
cyclic voltammetry (CV) experiments employing the classical
4
c). These varied emission wavelengths were related to the
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depicted in the Supporting Information (Figure S39). Reversible
oxidation and reduction potentials of GDYLC12 were
approximately 0.11 V and −1.19 V in the range of −2.0 ~ 2.0 V,
while those of compound 7 were approximately 0.20 V and
2
DOI: 10.1039/D0CC05959E
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ox
according to the formulae EHOMO = − (Eonset − E Fc/Fc+ + 4.8) eV,
red
E
E
LUMO = − (Eonset
− E Fc/Fc+ + 4.8) eV and ΔEcaled = ELUMO −
6
617−6628.
HOMO.3
8,39
The HOMO and LUMO energy values of GDYLC12
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were found to be −4.80 eV and −3.50 eV with an optical band
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compound 7 were found to be about −4.89 eV and −3.63 eV
with an optical band gap of 1.26 eV. Hence, the experimental
results indicated that GDYLC12 possessed a narrow optical
band gap. Compared with compound 7, GDYLC12 exhibited an
enhanced HOMO and LUMO energy level, and a slightly
broader energy band gap, which was ascribed to the larger
conjugation system of GDYLC12.
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In conclusion, we reported a C -symmetric GDY-core discotic
2
LC molecule bearing six symmetrical wedge-shaped 3,4,5-
tris(dodecyloxy)benzoate groups with 18 flexible alkyl chains.
This mesogen can self-assemble into cubic and hexagonal
columnar microstructures over a broad temperature range,
and possesses superior luminescence property and low optical
band gap energy. Most significantly, this GDY-derived discotic
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