Design, synthesis and photochromism studies of thienyl containing triarylethylene derivatives and their applications in real-time photoresponsive surfaces

Article abstract of DOI:10.1039/c8tc02698j

Thienyl containing triarylethylene derivatives, namely 2ThDpF and 3ThDpF, with photochromic properties have been designed and synthesized. These new photochromic molecules with simple chemical structures show fast-response and striking photochromic behavi

Full text of DOI:10.1039/c8tc02698j

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PAPER
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Nguyên T. K. Thanh, Xiaodi Su et al.
Fine-tuning of gold nanorod dimensions and plasmonic properties using
the Hofmeister effects
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Design, synthesis and photochromism study of thienyl containing
triarylethylene derivatives and their applications in real-time
photoresponsive surfaces†
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
a
a
a
a
a
DOI: 10.1039/x0xx00000x
Leyu Wang,‡ Tao Yu,‡* Zongliang Xie, Xiaojie Chen, Zhan Yang, Yi Zhang,* Matthew P. Aldred
a
and Zhenguo Chi*
www.rsc.org/
Thienyl containing triarylethylene derivatives, namely 2ThDpF and 3ThDpF, with photochromic properties have been
designed and synthesized. These new photochromic molecules with simple chemical structures show fast-response, and
striking photochromic behaviors in the solution-state, solid-state and in polymer films. Based on 2ThDpF, a real-time and
repeatable photoresponsive surface was fabricated. By UV-light irradiation for 1 minute, most of the 2ThDpF nano-
2
aggregates on the SiO substance changes from cone-shaped to hump-shaped and the contact angles of a water droplet
o
o
drastically increases from 43 to 95 simultaneously. The surface morphology and wettability can easily be reverted by
white-light irradiation for 5 minutes. The key issues to affect the real-time morphology and wettability changes are also
discussed in-depth based on the single-crystal analyses and TDDFT calculations. Therefore, these triarylethylene
derivatives with simple molecular structures are attractive in the areas of photochromism and photoresponsive surfaces.
process is uncontrollable due to the unstable ring-closure state.
(reverted to initial state as soon as the UV-light irradiation
Introduction
2
2
stopped). These shortcomings restricted their applications
and modification of the chemical structures are required for
-4 this photochromic system to realize the photochromism in the
solid state, solution-state and polymer films. Besides, tuning
the photochromic colors and achieving controllable reverted
photochromic processes are also quite required for this new
-9 photochromic system.
Photochromic materials that can exhibit reversible photo-
induced transformations between two or several well-defined
states have aroused enormous attention in recent years.
1
Nowadays, particular attention has been focused on their
various potential application in security markings, photo-
switchable molecular devices, optical memory storage systems,
5
chemosensing, bio-imagining and photoresponsive surfaces.
Tuning the morphologies and wettability of surfaces are of
great importance because it has much relation to
With the continuous efforts on the modification of the
chemical structures, many photochromic systems such as
1
0-12
13-15 optoelectronic devices fabrication, adsorption and biomedical
stilbene- and azo-containing compounds,
spirooxazine
spiropyran,
24-27
16,17
18-21
engineering.
Development of responsive surfaces based on
and dithienylethene derivatives
have
photochromic materials was considered as an ideal method
because light irradiation is considered as controllable, non-
contact, non-destructive stimuli. In previous reports,
morphology tunable surfaces based on diarylethene
derivatives and other photochromic materials have been
been designed and developed in previous researches. However,
the complex synthetic chemistry procedures highly resisted
the development of photochromic materials. Recently, our
group reported that triphenylethylene derivatives with simple
chemical structures display photochromic behavior in the
However, the photochromism for these
materials could not be realized in the solution-state or in
polymer films. Furthermore, the photochromic bleaching
2
8-30
31,32
22-23
systematically studied by Uchida,
groups
Kobatake,
and other
solid-state.
3
3-35
. For most of these reported photoresponsive
surfaces, different kinds of microcrystals (or aggregates in the
amorphous state) were formed on the substances by switching
the chemical structures using light irradiation. This kind of
photoresponsive surface shows good stability and
a
PCFM Lab, GD HPPC Lab, Guangdong Engineering Technology Research Center for
28-35
High-performance Organic and Polymer Photoelectric Functional Films, State Key
Laboratory of Optoelectronic Material and Technologies, School of Chemistry, Sun
repeatability.
However, these photoresponsive surfaces
are still suffer from long switching times (usually several hours)
and complex switching conditions (heating or solvent fuming
sometimes are required during the morphology switching).
Yat-sen University, Guangzhou, 510275, P.R. China. yutao33@mail.sysu.edu.cn
ceszy@mail.sysu.edu.cn chizhg@mail.sysu.edu.cn
Electronic Supplementary Information (ESI) available: Synthetic details of new
compounds, experimental details, details of single crystals, photophysical data,
supplemental figures and Crystallographic details (CIF). See DOI:
；
；
†
1
‡
0.1039/x0xx00000x
Dr L. Wang and Dr T. Yu contributed equally to this work.
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tunable wettability were fabricated with 2ThDpF. For the
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DOI: 10.1039/C8TC02698J
surfaces based on 3ThDpF, no photoresponsive properties
could be observed. The key factors leading to the diverse
photoinduced deformation properties with similar chemical
structures was revealed by single-crystal analyses and TDDFT
calculations.
Fig. 1 Chemical structures of 2ThDp, 2ThDpF, 3ThDp and 3ThDpF
Some photochromic materials display photoinduced
Results and discussion
36-39
deformation properties in the solid-state.
If obvious real-
Synthesis and characterization. The synthetic details of
compounds 2ThDp, 2ThDpF, 3ThDp and 3ThDpF are described
in the supporting information. All these compounds were
characterized by H NMR spectroscopy, high resolution EI mass
spectrometry and elemental analyses after chemical synthesis.
time and controllable photoinduced deformation could be
realized fast and reversibly in nano-aggregates on substance,
ideal photoresponsive surfaces might be achieved. Therefore,
reversible photoinduced deformation materials with short
responsive-times and simple chemical structures are in high
demand. The photochromism for triphenylethylene derivatives
is usually consistent with large conformational changes which
might lead to photoinduced deformations. Therefore, it is
quite appealing to developing new triphenylethylene based
photochromic materials with simple chemical structures, fast-
responsive time, controllable and decent photochromic
properties.
In order to produce new photochromic systems with
simple chemical structures, time fast-responsive, controllable
photochromism (bleaching) and realization of real-time
photoresponsive surfaces, a series of thienyl containing
triarylethylene photochromic materials have been rationally
designed and synthesized, as shown in Fig. 1. Compounds
1
Photochromic
photochromic properties could be detected for compounds
ThDp and 3ThDp, whilst 2ThDpF and 3ThDpF display obvious
Properties.
After
UV-irradiation,
no
2
color changes after UV-light irradiation. It can be expected that
by introducing fluorine atoms (F) into the triarylethylene
structure the ring-closure state can be stabilized, therefore,
3
,40
promoting the photochromic process.
previous literature,
Different from the
22,23
the photochromism for these
triarylethylene derivatives was no longer only present in the
solid-state. Degassed THF solutions of 2ThDpF and 3ThDpF
displayed color changes from colorless to yellow and orange,
respectively, after UV-light irradiation (365 nm). The color
changes can be ascribed to the ring-closure reaction according
2
ThDpF and 3ThDpF display obvious photochromic properties
22,23,41-43
to previous reports
and the mechanism is further
in the solution-state, solid-state and polymer films. Besides the
color changes, the emission properties for these two
compounds also drastically change during the photochromic
processes. Repeatable, real-time responsive surfaces with
confirmed vide infra. UV-vis absorption spectra for these two
compounds were measured during the photochromic and
bleaching processes. For these photochromic materials, the
-
3
Fig. 2 (a) Time-dependent UV-vis absorption spectra of 2ThDpF in degassed THF solution (1.0×10 M) upon UV-irradiation (365 nm), the inset show the photographs of 2ThDpF
-
3
THF solution before (left) and after (right) UV-light irradiation; (b) Time-dependent UV-vis absorption spectra of 3ThDpF in degassed THF solution (1.0×10 M) upon UV-light
irradiation (365 nm), the inset show the pictures of 3ThDpF in THF solution before (left) and after (right) UV-light irradiation; (c) Picture to illustrate the color changes and emission
changes for compound 2ThDpF and 3ThDpF after UV-light irradiation; (d) Time dependent UV-vis reflectance spectra of compound 2ThDpF during the photochromic process; (e)
Time dependent UV-vis reflectance spectra of compound 2ThDpF during the photochromic bleaching process; (f) Recycling of the photochromic process of compound 2ThDpF as a
function of exposure to UV-light (365 nm) and white-light for 10 seconds and 5 minutes, respectively.
2
| J. Name., 2012, 00, 1-3
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photochromic colors are easily tuned by changing the state for 2ThDpF (named 2ThDpF(C)) is quite stable in the dark.
attachment at the 2- or 3- positions of the thiophene ring. As Without white-light irradiation, the yellow color for 2ThDpF(C)
shown in Fig. 2(a) and 2(b), new absorption bands with the can be maintained for over 24 hours at ambient temperature.
maxima at 432 nm and 461 nm were detected for the The photochromic bleaching process of 2ThDpF can be
degassed THF solutions of 2ThDpF and 3ThDpF, respectively, completed within 300 seconds under white-light irradiation
upon UV-light irradiation. We have estimated the from a halogen lamp (Fig. 2(e)). The time-dependent UV-vis
photocyclization yields (ring-closure reaction) for 2ThDpF and reflectance spectra during the photochromic and bleaching
1
3
ThDpF by comparing the H NMR spectra before and after processes for the 3ThDpF were shown in Fig. S11 and S12.
UV- light irradiation in CD Cl solution at concentration of 1.0
×
Compared to 2ThDpF(C), the ring-closure state of 3ThDpF
3
-2
1
0 mol/L. However, for both compounds no changes could be (named 3ThDpF(C)) displayed a red-shifted absorption band
1
observed in the H NMR spectra after irradiation. We estimate with λmax = 468 nm after UV-irradiation. The red-shift for
the photocyclization yields for both 2ThDpF and 3ThDpF to be absorption of 3ThDpF(C) suggests increased conjugation for
less than 1%. The low photocyclization yields of 2ThDpF and the ring-closed state of 3ThDpF(C) compared to 2ThDpF(C).
3
1
ThDpF can also be noticed in concentrated solutions (1.0
0 mol/L) by the lack of noticeable color changes. Upon UV- during the photochromic process and negligible fatigue could
×
Compound 2ThDpF and 3ThDpF display good reversibility
-3
irradiation, almost no color changes could be detected for be detected after 20 photochromic and bleaching cycles (Fig.
these photochromic materials in the solution state with 2(f) and Fig. S13). Good recyclability of these photochromic
-5
concentration of ca. 1.0
×10 mol/L. On the contrary, obvious materials indicates their potential applications as rewritable
color changes of dithienylethene (DTE)-based photochromic and reversible materials. Besides the color changes, the
materials can be clearly be observed with concentration of ca. emission properties for these photochromic materials are also
-5
[18-21]
1
.0
×
10 mol/L.
After irradiation for 160 seconds and 75 responsive to UV-light irradiation. (Fig. 2(c)) This might be
seconds, the lower-energy absorption bands for the ring- attributed to the non-emissive properties for the ring-closure
closure structures of 2ThDpF and 3ThDpF (named 2ThDpF(C) states of 2ThDpF and 3ThDpF. The emission spectra for
and 3ThDpF(C)) were no longer enhanced, and with 2ThDpF and 3ThDpF before and after UV-light irradiation are
subsequent white-light irradiation, the colors of 2ThDpF(C) and shown in Fig. S14 and S15. We have investigated the
3
ThDpF(C) faded (Fig. S5 and S6). Thermal-back reactions (ring- aggregation states of compounds 2ThDpF and 3ThDpF powder
opening reaction in dark) of the photochromic materials in THF samples by pXRD analyses (Fig S16). The pXRD spectra indicate
-3
(
1.0×10 mol/L) were also investigated by time-dependent that the solid samples are crystalline in morphology. Single
absorption studies, at 303 K, in the dark. The time-dependent crystals of 2ThDpF, which were obtained by recrystallization
absorption spectra of compounds 2ThDpF and 3ThDpF are from a mixed solvent system of hexane-methanol, also exhibit
shown in Figure S7 and S8. The thermal-back reactions are some obvious photochromic properties as the powders
slow and the half-lives of 2ThDpF and 3ThDpF are ca. 9.55 and mentioned above. The UV-vis reflectance spectra and the
6
.44 hours, respectively (see Figure S9 and S10). This suggests photochromic pictures are shown in Fig. S17 to S19. The
relatively good bi-stability of the photochromic materials. In emission intensities for both compounds obviously decrease
the solid state, the half-life of the thermal-back reactions is after UV-irradiation. The color-emission dual-responsive
even longer due to the rigid environment.
In the solid-state, compounds 2ThDpF and 3ThDpF also advantageous for nondestructive read-out processes.
properties for these photochromic materials might be
44
exhibit obvious photochromic properties. After UV-light
The photochromic properties of these compounds were
irradiation (365 nm), both the colors and the emission also studied by doping 2ThDpF and 3ThDpF into poly(n-butyl
properties for 2ThDpF and 3ThDpF change, as shown in Fig. methacrylate) (PBMA) with the dopant concentration of 5 wt%.
2
(c). To further reveal the photochromic properties of 2ThDpF The flexible polymer films (with thicknesses of ca. 1 mm)
and 3ThDpF in the solid-state, time dependent UV-vis containing 2ThDpF and 3ThDpF display obvious photochromic
reflectance spectroscopy studies for the photochromic properties. By UV-light irradiation for ca. 3 minutes the films
processes and photochromic bleaching processes (ring- containing 2ThDpF and 3ThDpF change from colorless to
opening reaction under white-light irradiation) were yellow and deep orange, respectively. Consequently, the
performed. For 2ThDpF, a low-energy absorption band with emission properties of the polymer films also quench after the
λmax = 451 nm forms and gradually increases during UV-light photochromic processes. With white-light irradiation, the
irradiation. Different form other triarylethylene photochromic colors of the films fade with emission reversed.
2
2,23
materials reported in previous literature,
the ring-closed Photopatterning were performed by UV-light or white-light
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Fig. 3 Illustration of the photochromic-based photopatterning processes for polymer films containing 3ThDpF with the dopant concentration of 5 wt%: (a) Before UV-light
irradiation; (b) After UV-light irradiation; (c) After UV-light irradiation using photo-mask (observed under daylight); (d) After UV-light irradiation using photo-mask (observed under
UV-light); (e) The UV-light irradiated film further irradiated using white-light with photo-mask (observed under daylight); (f) The UV-light irradiated film further irradiated with
white-light with mask (observed under UV-light).
irradiation with a 2D-code mask. Fig. 3 shows the polymer film
containing 5 wt% 3ThDpF. An orange 2D-code pattern can be
clearly observed on the polymer films after UV-light irradiation
using a photo-mask. Furthermore, the 2D-code with black
color (non-emissive) could be detected on the polymer films
under UV-light. The message of 2D-codes (under daylight and
UV-light) can be directly recognized by cell phones with
relative programs. Besides, transparent 2D-code patterns have
also been achieved by white-light irradiation again using the
photo-mask on the orange polymer films (which have been
irradiated with UV-light). For the polymer films containing
Fig. 4 The photochromic mechanism for compounds 2ThDpF and 3ThDpF.
2
ThDpF, similar photopatterning can also be fulfilled (Fig. S20).
45
A pale-yellow pattern and a black pattern can be achieved
under daylight and UV-light, respectively. (Fig. S20c and S20d)
Fig. S21 and S22 depict the UV-vis reflectance spectra for the
photochromic bleaching processes of polymer films doped
with 2ThDpF and 3ThDpF. Like these molecules in solution and
solid-state, strong absorption bands at 446 nm and 461 nm
appear after UV-light irradiation of the polymer films
containing 2ThDpF and 3ThDpF, respectively. Compared with
the photochromism in the solution-state, the ring-closed state
for 2ThDpF and 3ThDpF are more stable in polymer films,
which is mainly due to the restricted environment in the rigid
polymer films. These photochromic polymer films show good
repeatability. No fatigue could be detected for polymer films
containing both 2ThDpF and 3ThDpF after 20 photochromic
cycles (Fig. S23 and S24). The high-contrast photochromism
with good repeatability for these photochromic polymer films
are attractive in areas of rewriteable paper, security markings
and optical memory storage systems.
According to the previous literature, the photochromic
response after irradiation is assigned to the ring-closure
reaction between the thienyl rings and the ethene-1,1-
41-43
diyldibenzene moieties.
For compound 3ThDpF, both 2-
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and 4- positions of the thienyl rings might be involved in the changes. It is discovered that most of the cone-sVhieawpAertdiclenOannlione-
ring-closure reaction. In an attempt to provide evidence for sized aggregates were divided and beDcOoIm: 10e.10h3u9m/Cp8T-sCh0a2p69e8dJ.
the photochromic mechanism and identify the ring-closure Consistent with the morphology changes, the contact angle
o
structure of 3ThDpF(C), dehydrogenation reactions were was increases from ca. 43 (before UV-light irradiation) to ca.
o
carried out for 2ThDpF(C) and 3ThDpF(C) and the final 96 (after UV-light irradiation). This drastic change for the
compounds were named 2ThDpF(O) and 3ThDpF(O), contacted angle is mainly attributed to the morphology
46
respectively. The details of the dehydrogenation reactions changes on the surface. More importantly, hump-shaped
are listed in the supporting information and the chemical nano-sized aggregates can be gradually changed to cone-
structures for 2ThDpF(O) and 3ThDpF(O) were unequivocally shaped with the contacted angles decreased to the initial state
1
1
1
confirmed by H NMR spectroscopy, H- H COSY NMR spectra, by white-light irradiation for 5 minutes. During the reverse
and high resolution EI mass spectrometry (Fig. S25 to S28). The process, intermediate states are easily achieved by controlling
chemical structure of 3ThDpF(O) indicates that the ring-closure the irradiation time (Fig. 5(b)). Surface-2ThDpF displays real-
reaction only occurs at the 2- position of the thienyl ring time, reversible photoresponsive surfaces and the
during the photochromic process. Therefore, the intermediate states between the ON/OFF states can also be
photochromic mechanism could be concluded as shown in Fig. achieved by controlling the white-light irradiation time. The
4
.
advantages of real-time photoresponsive surfaces based on
these triarylethylene derivatives could promote the
Real-time photoresponsive surface morphology and morphology changeable and wettability controllable materials
wettability. In an attempt to fabricate photoresponsive to industrial applications.
surfaces based on these photochromic materials, 2ThDpF and
The morphology studies and contact angle analyses were
3
ThDpF, with the thickness of ca. 200 nm, were deposited also performed for the surfaces based on 3ThDpF (surface-
onto identical pieces of SiO substrates by thermal evaporation. 3ThDpF) during the photochromic and bleaching processes. No
2
The thicknesses of the photochromic materials were obvious morphology changes and wettability changes for
confirmed by SEM studies (Fig. S29 and S30). Atomic force surface-3ThDpF could be detected during the photochromic
microscopy (AFM) studies and contact angle analyses were and bleaching processes of 3ThDpF (Fig. S31). It is interesting
performed to investigate the morphology and wettability to discover that the photochromic materials with quite similar
changes during the photochromic process. The surface based chemical structures display totally different photoresponsive
on
2ThDpF
(surface-2ThDpF)
displays
reversible properties on surfaces.
photoresponsive morphologies and wettability. As depicted in
the AFM spectra (Fig. 5), a large scale of cone-shaped nano- Single crystal structure analyses. Single crystals of 2ThDpF
sized aggregates could be observed on the surface-2ThDpF were obtained by recrystallization from hexane-methanol
before irradiation. AFM studies were performed again for the mixed solvent system and the CCDC number is 1574176. To
same area after UV-light exposure to monitor the morphology
Fig. 5 (a) AFM images and contact angles for the surface-2ThDpF before, after UV-light irradiation (1 minute) and further white-light irradiation for 5 minutes. (b) The morphology
reversed process for suface-2ThDpF after white-light irradiation (for 0 minute, 2.5 minutes and 5 minutes).
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Fig. 6 Single-crystal structure for compound 2ThDpF (the aryl rings and carbon atoms
involved in the photochromic reaction are labeled).
Fig.7 Optimized structures of 2ThDpF, 2ThDpF(C), 3ThDpF and 3ThDpF(C).
further investigate the packing mode and the conformational and the UV-vis absorption spectra.
structure for 2ThDpF in the “aggregated” state, single crystal
The optimized structures of 2ThDpF 2ThDpF(C) 3ThDpF and
structure analysis was carried out. Single crystals of 2ThDpF is 3ThDpF(C) are shown in Fig. 6 and the selected structural
based on Pbca space groups and the data for bond distances parameters are listed in Table S3-S6. The optimized structure
and angles are listed in Table S1 and S2 of the supporting of 2ThDpF is in accordance with the structure of the single
information. 2ThDpF molecules display two types of crystal analysis. The carbon atom in the thienyl ring, which is
conformations with slight differences in the crystalline state involved in the ring-closure reaction is also far away from the
(
Fig. 5). For both conformations, the three aryl moieties 4-fluorophenyl moieties. By comparison of the optimized
adopted twisted conformations, which can indeed decrease structures of 2ThDpF and 2ThDpF(C), it can be concluded that
the steric hindrance effect. The thiophene moieties are almost a great magnitude of rotation for the thienyl ring (almost ca.
o
perpendicular to the 4-fluorophenyl moieties at the same side 180 ) is required during the photochromic process. On the
of the double bonds. It is noted that C16 and C34 (labeled in contrary, the conformational structures of 3ThDpF and
Fig. 6), where the ring-closure reaction takes place, are far 3ThDpF(C) are similar and the ring-closure reactions can be
away from the 4-fluorophenyl moieties. The thiophene fulfilled with slight conformational changes. Therefore, the
o
moieties have to rotate almost ca. 180 to fulfill the drastic conformational changes between 2ThDpF and
photochromic ring-closure reaction. Therefore, the 2ThDpF(C) might lead to the morphology and wettability
conformation of 2ThDpF molecules have to be drastically changes in the “aggregation” states. The diverse
changed during the photochromic process. It is quite possible photoresponsive properties in morphologies and wettability
that the obvious morphology changes for the surface-2ThDpF for surface-2ThDpF and surface-3ThDpF are attributed to the
is ascribed to the drastic conformational changes for 2ThDpF different molecular conformational changes during the
during the photochromic process.
photochromic process. These results reveal that
photoresponsive morphologies and wettability for
DFT Calculations. In order to gain further insights into the photoresponsive surfaces are highly related with the
conformational information and photochromic properties, conformational changes that occur during the photochromic
density functional theory (DFT) and time-dependent density
functional theory (TDDFT) calculations at the B3LYP/6-31G*
level was performed for 2ThDpF and 3ThDpF both in the ring-
opened states and ring-closed states. The HOMO and LUMO
electronic distributions, bandgaps and vertical excitation
wavelengths for these compounds are listed in Table S7. The
HOMO and LUMO of the closed forms are the π and π* orbitals
that are delocalized at the 9a,9b-dihydronaphthothiophene
moieties, as depicted in Table S7. Based on the TDDFT
process. Choosing materials in which more obvious
conformational changes take place during the photochromic
process might promote improvements related to the
photoresponsivity of the morphology and wettability of
surfaces.
Conclusions
calculation, the lowest energy absorption band is red-shifted in In summary, thienyl containing triarylethylene photochromic
energy in 3ThDpF(C) (512 nm) relative to 2ThDpF(C) (480 nm),
which is in line with the trend observed in the color changes
materials 2ThDpF and 3ThDpF have been successfully
synthesized. These photochromic molecules provide decent
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1
7 X. Zhang, C. F. Chamberlayne, A. Kurimoto, N. L.ViFewraAnrtkiclae nOdnlinEe.
photochromic properties with good repeatability in the
solution-state, solid-state and in polymer-films.
Photopatterning experiments were carried out using PMBA
polymer films doped with these photochromic materials. Real-
J. Harbron, Chem. Commun., 2016, 52, 4144-4147.
DOI: 10.1039/C8TC02698J
1
1
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1
9
2
ThDpF. The morphology and wettability of surface-2ThDpF
2
2
was demonstrated in real-time and repeatedly tuned using UV-
light and white-light irradiation. By single-crystal analyses and
TDDFT calculations, it is revealed that the photoresponsive
2
7
morphology and wettability are highly related to the 23 T. Yu, D. Ou, L. Wang, S. Zheng, Z. Yang, Y. Zhang, Z. Chi, S.
Liu, J. Xu and M. P. Aldred, Mater. Chem. Front., 2017,
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1
,
conformational changes during the photochromic processes.
This study provides a series of photochromic materials with
1
2
2
2, 17036.
simple structures and
photoresponsive surfaces.
a
new strategy to fabricate
,
4
2
,
3
543-3552.
Conflicts of interest
There are no conflicts to declare.
27 Y. Hu, W. Zou, V. Julita, R. Ramanathan, R. F. Tabor, R. Nixon-
Luke, G. Bryant, V. Bansal and B. L. Wilkinson, Chem. Sci.,
2
016, 7, 6628-6634.
2
2
3
8 K. Uchida, N. Nishikawa, N. Izumi, S. Yamazoe, H. Mayama, Y.
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Acknowledgements
The authors gratefully acknowledge the financial support from
the NSF of China (51733010, 21672267, 51473185, 51703253),
Fundamental Research Funds for the Central Universities,
Guangdong Science and Technology Plan (2015B090913003,
2
017As3010295) and Educational Commission of Guangdong
3
3
3
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DOI: 10.1039/C8TC02698J
Journal Name
ARTICLE
Title: Design, synthesis and photochromism study of thienyl containing triarylethylene derivatives and their
applications in real-time photoresponsive surfaces
Photoresponsive Materials: Developing new photochromic materials with simple chemical structures, striking
photochromic properties and fabrication real-time morphologies changeable surfaces with tuneable wettability
based on these materials.
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