Dual-responding circularly polarized luminescence based on mechanically and thermally induced assemblies of cyano-distyrylbenzene hydrogen bonding liquid crystals

Article abstract of DOI:10.1039/c9cc09826g

Circularly polarized luminescence controlled by both mechanics and temperature was observed for the first time. The cyano-distyrylbenzene-cholesterol liquid crystals exhibited not only mechanochromism and thermochromism but also mechanically induced and thermally induced circularly polarized.

Full text of DOI:10.1039/c9cc09826g

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DOI: 10.1039/C9CC09826G
Authors
Shibing Chen,a Shengjie Jiang,a Jiabin Qiu,a Hongyu Guo*a,b and Fafu Yang*a,b,c
Affiliations
a College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007, P. R. China
b Fujian Key Laboratory of Polymer Materials, Fuzhou 350007, P. R. China
c Fujian provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, Fuzhou
350007, P.R. China
Acknowledgements
This work was financially supported by the National Natural Science Foundation of China (No:
21406036).

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Dual-responding circularly polarized luminescence based on the
mechanic- and thermo-induced assemblies of cyano-
distyrylbenzene hydrogen-bonding liquid crystal
Received 00th January 20xx,
Accepted 00th January 20xx
XXXX XXXX,a XXXX XXXX,a XXXX XXXX,a XXXX XXXX*a,b and XXXX XXXX*a,b,c
DOI: 10.1039/x0xx00000x
www.rsc.org/
The circularly polarized luminescence controlled by both mechanic architectural regulation of these molecular assemblies in the
and temperature was observed for the first time. The cyano- aggregated phase, implying a feasible design direction for the
distyrylbenzene-cholesterol liquid crystal exhibited not only development of efficient and multifunctional tunable CPL materials.
mechanochromism and thermochrochromism but also mechanic-
In order to regulate the molecular assembly behaviour, mechanic
induced and thermo-induced circularly polarized luminescence, and temperature were intensively used to control the mode of
which was attributed to the sensitive response of hydrogen bond molecular packing instead of alteration of the chemical structure, as
directed assemblies under different mechanic and temperature.
the noncovalent interactions were more likely to recover to original
covalent state by simply heating or recrystallization.8 Up to now, the
mechanoresponsive materials had been extensively studied with
reversible luminescent color changes,9 but the mechanic-induced
CPL property was not presented. On the other hand, the
temperature change usually induced the molecular stacking
changes of organic molecules. Especially, organic liquid crystals
exhibited the thermochrochromism and CPL properties based on
chirality transfer and amplification between chiral groups and
achiral fluorogens at different phase under various temperature.10
However, to the best of our knowledge, the reported organic liquid
crystals with CPL properties responded to the temperature only, no
dual- or multi-responding CPL liquid crystal was concerned so far.
Obviously, the dual- or multi-responding CPL properties have the
special advantages in promising applications such as high-security
system which are deserved to be studied significantly and urgently.
In this paper, we wish to report the dual-responding CPL property
induced by both mechanic and temperature for the first time. The
cyanodistyrylbenzene-cholesterol (CDB-1Ch) showed not only
mechanochromism and thermochrochromism but also mechainc-
induced and thermo-induced circularly polarized luminescence
based on its asymmetrical hydrogen bond-directed assemblies.
As the cholesterol unit had been used successfully for producing
thermoresponsive CPL properties,10a,10b and hydrogen bond
contributed to achieve mechanoresponsive signals,11 they were
combined to construct the target molecules with both mechanic-
induced and thermo-induced CPL properties. Thus, compounds
CDB-1Ch and CDB-2Ch were designed and synthesized in good
yields (See SI). They not only fused cholesterol unit and hydrogen
bond together but also possessed the asymmetrical or symmetrical
structures, which were favourable for studying the relationship of
structure and property for these novel AIE liquid crystals.
Circularly polarized luminescence (CPL) of organic and polymeric
materials at aggregated phase has attracted considerable attention
due to their promising applications in light emitting diodes, color-
image projection, optical information storage, stereoscopic displays,
etc.1 Particularly, the materials with switching CPL properties (i.e.
intensity or wavelength) in response to external stimuli such as heat,
light, solvent and pH are intriguing from both a fundamental and
application perspective.2 However, such smart materials are still
quite rare and the in-depth theoretical understanding of chirality
transfer and amplification for these materials with achiral
fluorogens were also rather limited up to now.3
The CPL response which reflects the chirality of materials in the
excited electronic state not only relies on chiral functions on the
molecular level, but also depends on the architectures of the
molecular assemblies for the reason that molecular aggregates
have specific physicochemical behaviors different from those of
individual molecules in both their ground and excited states.4 In
principle, helically organized aggregates formed by specific
intermolecular interaction showed characteristic CPL behaviors.5
Kawai's group reported that the one-dimensional aggregates
formed in methylcyclohexane exhibited twice the value of
luminescence dissymmetry factor (glum) when compared with the
spherical aggregates formed in chloroform at higher concentration.6
Song etc presented a supramolecular assembly of nanofibers
bearing a CPL response with glum of 0.6×10-3.7 These studies
suggested that switching CPL could be induced through
a. XXXXXXXXXXXX
b. XXXXXXXXXXXX.
c. XXXXXXXXXXXX.
Electronic Supplementary Information (ESI) available: Experimental details,
supporting figures and table. See DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
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monomeric pholuminescence. This proposal was alsoVcieownAfritricmleeOdnlibnye
that its emission of monomer after grindDinOgI:w10a.s10c3o9n/Cs9isCteCn0t98w26itGh
that in THF-H2O solution (as shown in Figure S41 for AIE property
with green emission at 513 nm in THF-H2O solution). Moreover, by
exposing the ground sample to a vapor of CH2Cl2 for 5 min, the
“yellow” fluorescence state was restored, indicating the reversible
MFC property for CDB-1Ch. The same emission color and XRD-
pattern suggested that the fumed sample had the same molecular
arrangement as that of pristine sample (Figure S15 and S16).
Figure 1. The structures of CDB-1Ch and CDB-2Ch.
Firstly, the initial samples and ground samples of CDB-1Ch and
CDB-2Ch were prepared for mechanofluorochromism(MFC) study.
For CDB-1Ch, the initial sample obtained by adding petroleum ether
into its CH2Cl2 solution showed an intense yellow-light emission
with peak at 572 nm. As expected, the fluorescence color altered
from yellow to green with maximum emission at 516 nm after
grinding (Figure S15). Such fluorescence modulation was attributed
to mechanic-induced phase transition between crystalline state and
amorphous state.8d,11d,12 Thereby, powder X-ray diffraction (XRD)
was performed to determine the MFC mechanism. Owing to the
lack of intense and sharp diffraction peaks in the XRD profile,
pristine powder was more likely an amorphous state (Figure S16).
Nevertheless, the vanishment of Bragg reflection at 14.9o and the
emergence of 16.3o unequivocally implied that pristine and ground
powder adopted distinctly different assembled structures. On
considering that hydrogen bond among adjacent molecules seemed
to be a critical driving force to induce the formation of the two
distinctive assemblies, the FT-IR spectrometry was applied to
provide structural insight into the two molecular aggregates and an
in-depth understanding of the change in emission behavior. As
illustrated in Figure S17, the peak at 1711 cm-1 for pristine powder
shift to a higher wavenumber region at 1726 cm-1 upon grinding,
indicating the partial destruction of hydrogen bonds stemmed from
C=O and the transformation of assembled structures. However, it
seemed counterintuitive that the N-H stretching vibration shift to
3339 cm-1 after grinding, lower than that of the pristine powder
(3364 cm-1) obviously, suggesting the formation of much stronger
hydrogen bonds. Careful examination of the structure of CDB-1Ch
might account that this shift could be ascribed to another H-donor
derived from amino group but not amide group (Figure 2a).
Formation of intermolecular H-bonds between amino groups would
require rotation of superimposed molecules by a certain angle.
Such twisted organization resulted in a less linear H-bond between
amide groups, agreeing with a weaker H-bond illustrated by
increasing wavenumber of C=O. Monomer to excimer transition
mechanism had been well documented in MFC mechanism.11b-11d
For excimers, emission bands were always located at wavelengths
higher than monomer emission bands and substantial π-π overlap
of luminescent cores was indispensable for excitonic and excimeric
coupling. Based on the above model, it was possible that the large
fluorescence spectral discrepancy between the pristine and ground
state of CDB-1Ch might originate from different emitting species in
the excited states. For pristine state, parallel molecular-packing
architectures rendered it substantial π-π overlap of fluorophore,
resulting in higher wavelengths emission. However, due to the
dramatically reduced π-π overlap between adjacent molecules as a
result of twisted organization in ground state, the formation of a
photoexcited excimer was prohibited, leading to the predominant
Figure 2. The MFC mechanism of (a) DCB-1Ch and (b) DCB-2Ch.
As for CDB-2Ch, both the ground and initial states show yellow
emission and only a small blue shift (10 nm) appeared under
mechanical grinding (Figure S18), suggesting that the symmetric
substitution of cholesterol units induced different stacking mode
from that of CDB-1Ch. The microstructure of pristine and ground
samples could not be distinguished by XRD measurements and FT-IR
spectra because of little difference (Figure S19 and S20). These
results suggested the similar hydrogen-bond modes between the
two adjacent molecules in these two assemblies of CDB-2Ch (Figure
2b). The slightly twisted organization of ground sample resulted in
little decrease of π-π overlap of fluorophore by compared with that
of CDB-1Ch. Owing to the substantial π-π overlap of luminescent
cores in both the two assemblies, excimer to excimer transition
mechanism accounted for the little wavelength shift. Their yellow
excimer emission was different from the characteristical blue
monomer emission in dilute THF solution (as shown in Figure S42
for AIE property of CDB-2Ch with green emission at about 513 nm).
Next, it was interesting to study the CPL properties and circular
dichroism spectra (CD) based on the twisted organization of ground
sample in comparison with the parallel stacked molecules in pritine
sample. For CDB-1Ch, the pristine powder has no CPL signal,
implying its molecular packing mode was unfavorable for helical
structures (Figure S21). However, dramatically enhanced CPL signal
with a glum value of -1.1 x 10-3 appeared upon the application of
mechanical force (Figure S22), suggesting the generation of a
mechanic-induced helical assemblies. The high-contrast CPL
switching was supported by CD data which reflected the chiral
nature of the aggregates in the ground state. The ground sample
showed strong cotton effect (gabs = 5.73×10-3) while the pristine
sample has no CD signal in UV–vis spectra (Figure S24, S25 and S46).
The silent CPL response for fumed sample indicated the CPL “OFF”
state can be restored by exposing it to DCM vapors (Figure S23).
Hence, the reversible mechanic-induced CPL property was achieved
2 | J. Name., 2012, 00, 1-3
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by modulation of the assembled structure for the first time. The collapsing broken fan-shaped texture (Figure S32) and the
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o
experimental results of emission anisotropic spectra were also in formation of new Col texture at 165 CD(OFIi:g1u0r.e103S93/3C)9.CTCh0e98X2R6GD
accordance with the CD and CPL results (Figure S48).
pattern at 165 °C showed a large number of Bragg reflections,
On the other hand, CDB-2Ch showed negative cotton effect (gabs agreeing well with a rectangular columnar (colr2, a = 55.0 Å, b = 34.3
= 2.46×10-3) in CD spectra, implying the effective transfer of Å) lattice (Figure 5 and Table S1). Based on XRD data, the Z value for
chirality from the peripheral cholesterol moiety to achiral aromatic per columnar slice of Colr2 was calculated as 8, which was smaller
rigid core in the ground state because of the small twisted than that of Colr1. The glum value (-4.2 x 10-3, Figure S38) for Colr2
organization (Figure S26, S27 and S47). But both the pristine and was almost only half that for colr1. The decline of glum value was
ground solid state exhibited silent CPL response, which might be ascribed to the decrease of packing order of intracolumnar helical
explained by that the small twisting was not enough for CPL arrangement due to the longer interlayer distance compared to
induction (Figure S28 and 29). Hence, the effective π-π overlap that of colr1. The weaker H-bond and other intermolecular
based on symmetrical structure offered the ground sample of CDB- interaction such as cholesterol-cholesterol and π-π interaction
2Ch a totally different electronic nature in the excited state resulted in a longer interlayer distance at higher temperature.
although it possessed the same luminescent core with CDB-1Ch.
Owing to the similar stacking mode but loser helical-like
Furthermore, the thermochrochromism and thermo-induced CPL architectures which inhibited the formation of excimers, the
properties based on their liquid crystalline behaviors were studied. molecules in colr2 behaved as monomer and showed green
Their DSC, POM and XRD analysis were exhibited in Figure S30-34 luminescese similar to that of colr1 (Figure S35). The texture of Colr2
and Table S1. CDB-1Ch displayed thermochrochromism and an transferred to isotropic liquid at 220 °C although no obvious
endothermic peak at 79 °C on the second heating, suggesting that endothermic peak was detected at about 220 °C in DSC profile. The
the luminescent color change from yellow (571 nm) to green (510 weak and random intermolecular interaction leaded to destruction
nm) was related to the phase transition from solid to a birefringent of helical assembled structure and a silent CPL response (Figure
mesomorphic (M) phase (Figure S35). Broken fan-shaped texture S39). The coexistence of excimeric and monomeric emission might
appeared at thermotropic mesophase from 79 °C to 162 °C, which explain the fluorescence at 527 nm due to such random orientation.
could be also assigned to columnar phase (Figure S31). The
2000
145 °C
observed XRD pattern was characteristic for a columnar rectangular
(11)
1600
mesophase (Colr) of p2mm symmetry with lattice parameters a =
61.4 Å and b = 42.7 Å (Figure 3 and Table S1).13 Based on equation Z
1200
(22)
800
= ρNAAh/Mr (ρ, NA, A and h are the density of the mesophase,
Avogadro’s constant, columnar cross section (a×b) and the height of
400
(20)
(32)
(33)
(21) (41)
(001)
20
(55)
(44)
0
the columnar unit, respectively),14 the number of molecules per
columnar slice was estimated to be 10. On the other hand, CPL
property of this mesophase (Colr1) was investigated and the
negative CPL signal with glum value of 1.0 x 10-2 (Figure 3 and S37),
implying a highly ordered helical column in contrast to the silent
response at ambient temperature. The higher glum value than that
of ground state indicated the more ordered helical stacks in
columnar mesophase (Figure 4). The adjacent molecule required
relative rotation to accommodate them in a tilted column which
0
5
10
15
25
30
35
Scattering angles (2θ)
confined the orientation of CDB-1Ch to a partially overlapped Figure 4. The XRD trace of DCB-1Ch in mesophase at 145 °C and the
architecture in the excited state. The green luminescence was
assigned to monomer emission, which was consistent with the
model in Figure 2 since the assembled structure of pristine powder
contained such twisted structure unit as well.
proposed molecular stacking in rectangular columnar mesophase.
165 oC
140
0.02
120
100
80
0.06
240 °C
DCB-2Ch
DCB-1Ch
145 °C
0.01
0.00
5.6 x 10-2
0.03
0.00
-0.01
1.0 x 10-2
-0.03
18
-0.02
70
35
0
12
6
-35
-70
0
-6
0.03
60
(55)
0.4
0.2
0.0
531 nm
(45)
510 nm
0.02
0.01
0.00
(13)
40
(22)
(04)
(33)
10
450
475
500
525
550
575
600
625
650
(11)
450
500
550
600
650
700
750
800
20
0
Wavelength (nm)
Wavelength (nm)
Figure 3. CPL spectra of DCB-1Ch and DCB-2Ch at mesophase.
5
15
20
25
30
35
40
45
Scattering angles (2θ)
When further heated to 160 °C, the Colr1 of CDB-1Ch became Figure 5. The XRD trace of DCB-1Ch in mesophase at 165 °C and the
unstable and the molecule blocks were rearranged into another Col
mesophase confirmed by an endothermic peak at 162 °C, the
proposed molecular stacking in rectangular columnar mesophase.
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Scattering angles (2θ)
Figure 6. The XRD trace of DCB-2Ch in mesophase at 240 °C and the
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mechanical force, dramatically high glum of +5.6 x 10-2 (Figure 3, S40
and Figure S45) was observed at Colr phase, which was the result of
the intracolumnar helical arrangement driven by thermodynamic
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deduced that both CDB-1Ch and CDB-2Ch possessed the
thermochrochromism and thermo-induced CPL with high glum values
based on various molecular assemblies of different H-bonds.
In conclusion, this paper prepared two cyanodistyrylbenzene-
cholesterol liquid crystal with asymmetrical or symmetrical H-
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sensitive mechanic and thermal response of molecular assemblies
directed by H-bond. This phenomenon was observed for the first
time, opening an new strategy for design and synthesis of new CPL
materials with multi-response abilities for external stimuli.
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This work was financially supported by XXXXXXXXXXX.
15(a) F. Song, Z. Zhao, Z. Liu, J. W. Y. Lam and B. Z. Tang, J. Mater. Chem. C, 2020,
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Notes and references
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145 °C
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DOI: 10.1039/C9CC09826G
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Scattering angles (2θ)
The circularly polarized luminescence controlled by both mechanic and
temperature was observed for the first time