Photosalient Effect of Diarylethene Crystals of Thiazoyl and Thienyl Derivatives

Article abstract of DOI:10.1002/chem.201900811

The photoresponse of diarylethene crystals is found to depend on the intensity of UV light, that is, photoinduced bending is switched to photosalient phenomena by increasing the light intensity. The change in the size of the crystal unit cell upon UV irra

Full text of DOI:10.1002/chem.201900811

A Journal of
Accepted Article
Title: Photosalient effect of diarylethene crystals of thiazoyl and thienyl
derivatives
Authors: Kingo Uchida, Yuma Nakagawa, Masakazu Morimoto,
Nobuhiro Yasuda, Kengo Hyodo, Satoshi Yokojima, and
Shinichiro Nakamura
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Photosalient effect of diarylethene crystals of thiazoyl and thienyl
derivatives
Yuma Nakagawa,[a] Masakazu Morimoto,*[b] Nobuhiro Yasuda,[c] Kengo Hyodo,[a] Satoshi Yokojima,[d],[e]
Shinichiro Nakamura,[e] and Kingo Uchida*[a],[e]
Abstract: The photo-response of diarylethene crystals is found to
depend on the intensity of UV light, i.e., photoinduced bending is
switched to photosalient phenomena by increasing the light intensity.
The size change in crystal unit cell upon UV irradiation is larger for
asymmetric diarylethenes having thiazole and thiophene rings than
for corresponding symmetric diarylethenes. As a result, the crystals
of an asymmetric diarylethene show much more drastic photosalient
effects than do the corresponding symmetric diarylethene crystals
upon UV irradiation. We also discover that the crystals of
diarylethene, which had no previous report of a photosalient effect,
show photosalient phenomena upon irradiation with strong UV light.
We further report the dependence of photosalient phenomena on the
size and shape of the crystals.
bending and twisting phenomena are commonly observed in
diarylethene crystals.[12,13] Recently, we synthesized
diarylethene having perfluorocyclohexene ring with two
thiazole rings. The thin crystals of this diarylethene prepared by
sublimation showed photochromism as well as the photosalient
effect.[14] Specifically, they showed bending, jumping, and
scattering upon UV irradiation.[14]
In this work, symmetric diarylethenes 1o and 2o were
synthesized, where 1o[15] has thiazole rings and 2o[16] has
thiophene rings at both ends of the molecule (Scheme 1).
Photochromism in these solutions has already been
reported.[15,16] Photoinduced bending behavior of the crystals has
also been reported, whereas no photosalient phenomena has
been reported.[12,17] We prepared an asymmetric diarylethene 3o
(Scheme 1) according to a previous paper.[18] We prepared the
crystals of 1o, 2o, and 3o by recrystallization from hexane
solutions as well as by sublimation. As a result, photo-induced
phenomena were observed in all three of these crystals.
a
a
Introduction
The scattering phenomenon of artificial crystals by light stimuli is
called the photosalient effect.[1–11] The first organic photosalient
effect was reported by Trommsdorff in 1834 on the bursting of
crystals of -santonin after they turned yellow by exposure to
sunlight.[1] The photosalient effect has recently been the subject
of further investigations.[4] Naumov et al. intensively studied the
crystal jumping and breaking that resulted from strong light
stimuli. Consequently, they named this the photosalient effect.[5-
10]
Diarylethenes are thermally stable photochromic compounds
that undergo cyclization and cycloreversion reactions upon
alternate irradiation with UV and visible light.[11] Photoinduced
[a] Y. Nakagawa, Dr. K. Hyodo, Prof. K. Uchida*
Department of Materials Chemistry
Faculty of Science and Technology, Ryukoku University, Seta
Otsu, Shiga 520-2194, Japan
E-mail: uchida@rins.ryukoku.ac.jp
[b] Prof. M. Morimoto*
Department of Chemistry and Research Center for Smart Molecules
Rikkyo University, 3-34-1 Nishi-Ikebukuro, Toshima-ku
Tokyo 171-8501, Japan
E-mail: m-morimoto@rikkyo.ac.jp
[c] Dr. N. Yasuda
Japan Synchrotron Radiation Research Institute
1-1-1 Kouto, Sayo-cho, Sayo-gun, Hyogo 679-5198, Japan
Scheme 1. Molecular structures of diarylethenes 1, 2, and 3.
[d] Prof. S. Yokojima
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences
1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Results and Discussion
[e] Prof. S. Yokojima, Dr. S. Nakamura, Prof. K. Uchida*
RIKEN, Cluster for Science, Technology and Innovation Hub
Nakamura Laboratory, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Although, synthesis of 3 was carried out by a microflow system,
the photochromic properties were not considered in that earlier
work.[18] We first investigated the absorption spectral changes of
3 in hexane solution (Figure S1). Open-ring isomer 3o has an
Supporting information and the ORCID identification number for the
author of this article can be found under
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These results are consistent with previous reports.[15,16] Upon
irradiation by the same weak intensity of UV light ( = 365 nm,
810 W cm-2), the crystal 3o displayed both coloration and
photosalient phenomena when irradiation was prolonged (80 s)
(Figure 1e and f, Movie S1).
Upon strong UV irradiation ( = 365 nm, 277 mW cm-2) to the
crystals prepared by recrystallization from hexane solutions, all
crystals of 1o, 2o, and 3o showed remarkable photosalient
phenomena on their surfaces accompanied with coloration
(Figure 2, Figure S2-4). A schematic illustration showing the
differences is also given in Figure 2g-i. To compare the crystals’
reactivity and deformation, we conducted X-ray analysis of these
crystals of open- and closed-ring isomers upon 400-nm light
irradiation for
1 min under the same conditions (results
summarized in Table S1). Graphical images of the deformations
for each crystal are depicted in Figure 3.
Under UV irradiation ( = 365 nm, 277 mW cm-2), cracks
appeared on the surface of 1o crystals perpendicular to the long
axis, followed by the crystal surface being cast off. Moreover,
flipping[5] of the peeled[20] crystalline surface was also observed
(Figure 2a and b, Figure S2). This is due to shrinkage of 0.50%
along the a-axis, which is parallel to the crystal’s long axis
(Figure 2a, Table S1). When the crystals are thin, the crystal
showed reversible shrinkage and elongation by alternate
irradiation with UV and visible light. When the aspect ratio of 1o
crystal is high, the crystal showed bending concave to the
incidence of UV light.[12] In our case, the crystal is thick enough
not to bend, and only the surface was photo-converted to 1c and
shrank along the long axis of the crystal (a-axis). Then cracks
were generated perpendicular to the a-axis. Each fragmented
crystal showed bending and dispersion on the surface (Figure
2g, Movie S2). At the same time, flipping of the crystals was also
observed (Figure S2, Movie S3).
Figure 1. Photochromism of single crystals of diarylethenes (1o): (a) and
(b), (2o): (c) and (d), and (3o): (e) and (f). Before UV irradiation: (a, c, e)
and after UV irradiation: (b, d, f). Scale bars: 200 m for (a, b, e, f), and
100 m for (c, d).
For the crystals of 2o, cracks in the vertical and horizontal
directions appeared on the surface. Upon UV irradiation ( = 365
nm, 277 mW cm-2), the crystalline surface collapsed (Figure 2c
and d, Figure S3). Diarylethene 2o also changed its molecular
size in the crystal, and ribbon shaped crystals have been
reported to show complicated helical deformation, depending on
the direction of the incident light.[17] This is due to the
herringbone orientation of 2o molecules in the crystals, where
two conformers exist in a unit cell. The size changes of the unit
cell of 2o were the smallest among those of the three derivatives,
so only a modest photosalient phenomenon was observed for
2o. Nevertheless, it is significant that small-fragment scattering
was observed on the surface during UV irradiation (Figure 2h,
Movie S4). The cracking pattern may be attributed to the release
of photo-induced shrinkage of the a- and c-axes (indicating
shrinkage of the crystal’s surface area) with the expansion
caused by elongation of the a-axis (vertical direction of the
absorption band at 295 nm in hexane. Upon UV irradiation, the
colour of the solution turned purple and a new band appeared at
550 nm, which is attributed to 3c. Upon visible light irradiation,
the colour disappeared and the band of 3o was regenerated.
Absorption coefficients and quantum yields are summarized in
Table 1, together with those of 1 and 2. The absorption maxima
of open- and closed-ring isomers and the quantum yields of
photochromic reactions (cyclization (o→c) and cycloreversion
(c→o)) closely approximate the values averaged between the
corresponding symmetric derivatives 1 and 2. This has often
been observed in other asymmetric diarylethene derivatives.[18,19]
The photochromism of 1o and 2o in crystalline states has
already been reported. A single crystal of newly prepared 3o
also showed photochromism upon alternate irradiation with UV
and visible lights. Upon UV irradiation at weak intensity ( = 365
nm, 810 W cm-2) for 30 min, crystals of 1o and 2o showed
coloration without any photosalient phenomenon (Figure 1a-d).
Table 1. Photochromic properties of diarylethene 1, 2, and 3 in hexane solution.
max / nm ( / 104 M-1 cm-1)

Compound
o→c (313 nm)
c→o (492 nm)
Open-ring isomer
Closed-ring isomer
1[15]
2[16]
3
0.32
0.59
0.25
0.020
0.013
0.013
300 (3.4)
280 (3.6)
295 (3.5)
525 (1.0)
575 (1.6)
550 (1.5)
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Figure 2. Photosalient effect of single crystals of diarylethenes (1o): (a) and (b), (2o): (c) and (d), and (3o): (e) and (f). Before UV irradiation ( = 365 nm,
277 mW cm-2): (a), (c) and (e) and after UV irradiation: (b), (d) and (f). Scale bars: 100 m. Schematic illustration of the differences in photosalient
phenomena of 1o: (g), 2o: (h), and 3o: (i).
surface). The direction of photoinduced size changes is different
from those found in other crystals (Figure 2c, Table S1).
Therefore, cracking perpendicular to the long axis of the crystal
such as 1o was not observed for 2o; instead, irregular breakage
of the crystal surface was observed. From the recrystallization of
2o in a hexane solution, not only rod-shaped but also cubic-
shaped crystals were obtained. In spite of the difference in the
crystal habit, both types of crystals have the same crystal
structures. Peeling phenomena were observed for both of them
(Figure S3, Movie S5).
Upon UV irradiation to the single crystal of 3o, a drastic
collapse of the crystal surface was observed. Small cracks were
initially generated perpendicular to the long axis on the surface,
then drastically larger cracks were generated along the long axis
and the whole crystal was scattered (Figure 2e, f and i, Movie
S6). The initial cracks on the surface are attributed to the
shrinkage of the a-axis of the unit cell, and as a result only
cracks appeared while no breaking of the crystal followed in this
direction. On the other hand, the b-axis of the unit cell expanded
at the maximum ratio in these crystals (Table S1). The direction
corresponds to the increase in the widths of 3o crystals.
Therefore, this induced tearing along the long axis of the 3o
Figure 3. Crystal lattice fluctuation of 1o (a), 2o (b), and 3o (c) upon
crystals.
In this study, we examined the correlation of area, thickness,
400-nm light irradiation.
and volume of crystals, with respect to the latent periods until
the development of the photosalient effect, for three types of
diarylethene bulk crystals. There was no such correlation in the
latent periods until the appearance of crystal surface cracks
commonly found in the three types of diarylethene crystals as
shown in the supplement (1o: Figure S6, 2o: Figure S7, and 3o:
Figure S8). This is because UV light (= 365 nm) is absorbed on
the crystal surface and light does not reach the backside of the
crystal. That is, in a crystal the dye highly concentrates, and thus
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the entire molecules in the crystal do not isomerize.[12] The
photosalient phenomenon originates in the tension between
non-reacted interior and the reacted surface. Therefore, the
photosalient phenomenon on the crystal surface has no
correlation with the area, thickness and volume of the crystals.
In contrast, for the phenomena occurring in the whole crystal,
the latent periods for each crystal and the corresponding
phenomena are different from each other. Therefore, it is
necessary to examine a correlation between crystal area,
thickness and volume as mentioned by Naumov.[5] Actually, the
tearing of 3o crystals has dependence on the thickness of the
crystal, and a thicker crystal takes more time to tear. In fact, in
crystals with a certain minimum thickness, cracks were observed
only on the surface, but such crystals never split (Figure 4).
the most dramatically impressive photosalient phenomena were
again observed for 3o crystals.
We next attempted to confirm whether the photosalient
phenomena observed here were due to the strain caused by the
photoisomerization, i.e., we investigated the thermal effect due
to the strong UV irradiation. During the strong UV irradiation, the
temperature of each surface was monitored by thermography
(testo 882). Even upon strong UV irradiation, the temperature on
the crystals remained nearly unchanged (at room temperature
(24-26 °C): temperature increase due to UV irradiation; 0.9 ±
0.3 °C, under cooling (at 3-5 °C): it was 0.6 ± 0.5 °C).
Accordingly, we conclude that the contribution of temperature
rising was negligible (Figure S10-S18).
Large changes in the unit cell of the crystals induced rapid
responses of the photosalient effect. The relationships of latent
periods to light intensities for these crystals are summarized in
Figure 5. Naturally, irradiation with stronger light shortens the
latent periods. With relatively weak intensities of light (below 300
mW cm-2), the responsiveness of the salient phenomena (i.e.
shorter latent periods) was 3o > 1o > 2o. This order is in
agreement with the order of the relative axis changes of the unit
cells.
Figure 4. Illustration of crystal (a) and the latent periods of photosalient
effect (tearing) by area (b), thickness (c), and volume (d) for crystal 3o
under UV irradiation ( = 365 nm, 277 mW cm-2).
X-ray crystallographic analysis of 3o was carried out, and the
results were compared with those of 1o and 2o. The 400-nm
light was irradiated for 1 min for all crystals, and the deviation of
the crystal axis was monitored. The data are summarized in
Table S1. Upon 400-nm light irradiation for 1 min to a crystal of
1o, the a-axis shrank by 0.50%, while the b- and c-axes
expanded by 0.50, and 0.19%, respectively. As a result of these
changes, the volume of a unit cell expanded by 0.20%. For a 2o
crystal, the a-axis expanded by 0.41%, while the b- and c-axes
shrank by 0.24, and 0.04%, respectively. As a result of these
changes, the volume of a unit cell expanded by 0.26% under the
same irradiation.
For a 3o crystal, the a-axis shrank by 0.73%, while the b- and
c-axes expanded by 0.89, and 0.13%, respectively. The large
shrinkage along the a-axis induced cracking, and the expansion
along the b-axis induced tearing. Then the unit cell volume of the
3o crystals expanded by 0.35%, which was the largest change
among the three crystals. Furthermore, the largest changes
among all axes were observed for the crystal of 3o; such
changes in 1o were moderate, and those in 2o were the
smallest. As a result of having the largest overall changes, the
crystal of 3o has shown the most dramatic photosalient
phenomena among the three derivatives. Such dramatic
phenomena were observed in Naumov’s system.[5,21] Here, each
fragmented surface crystal also jumped or scattered, and in fact
Figure 5. Relationship between UV light intensity ( = 365 nm) and latent
periods for single crystals of 1o (red circles), 2o (blue triangles), and 3o
(violet squares). Focusing on the peeling phenomenon, the latent periods
were calculated for the photosalient effect.
The results mentioned above indicate that the photosalient
phenomena on the crystalline surface of bulk crystals obtained
by recrystallization are independent on crystal size. However,
the photosalient (tearing) phenomena of the thin crystals
prepared by sublimation showed dependence on the thickness
of crystals. For the thin crystals of 1o and 2o, photoinduced
bending phenomena were already been reported, but there has
been no report on photosalient phenomena.[12,17] The crystal
structures of thin crystals have been reported to be the same as
those of bulk crystals of 1o and 2o prepared by
recrystallization.[12,17] Moreover, the structure of the thin crystals
of 3o was the same as that of bulk crystals from recrystallization.
(Table S2, Figure S19). We prepared thin crystals of 1o, 2o, and
3o by sublimation and observed their photoreactive motions
upon weak ( = 365 nm, 810 W cm-2) and strong ( = 365 nm,
277 mW cm-2) UV light irradiation. Initially, weak UV light was
irradiated to the crystals. Consequently, they showed
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Figure 7. Photosalient effect of thin crystals of diarylethenes (1o): (a) and
(b), (2o): (c) and (d), and (3o): (e) and (f). Before UV irradiation ( = 365 nm,
277 mW cm-2): (a), (c) and (e), and after UV irradiation: (b), (d) and (f). Scale
bars: 100 m.
Figure 6. Photoinduced bending of thin crystals of diarylethenes (1o): (a)
and (b), (2o): (c) and (d), and (3o): (e) and (f). Before UV irradiation ( =
365 nm, 810 W cm-2): (a, c, e) and after UV irradiation: (b, d, f). Scale
bars: 100 m.
photoinduced bending as reported,[12,17] where no photosalient
phenomena occurred (Figure 6).
were certainly switched as a function of the intensity of UV light
(810 W cm-2 or 277 mW cm-2). Recently, Chizhik and co-
workers proposed an elaborated model to describe the
photoinduced bending motion of molecular crystals.[22] Although
their model is quite general, the light intensity considered in their
study is much weaker than that in our study. It will be interesting
to investigate the threshold between the bending and salient but
it is beyond the scope of this paper.
The strong UV light was then irradiated to the same thin
crystals (Figure 7). Now, instead of bending, the thin crystals of
3o, among the three types, showed distinct photosalient
phenomena. The thin crystal of 1o showed bending followed by
scattering into small pieces. The thin crystals of 2o also showed
bending with strong UV light. Some thin crystals of 2o showed
cracking without bending (Figure S20). As soon as the UV light
was irradiated to the thin crystals of 3o, they immediately and
explosively broke down (Figure 7e and f, Movie S7); they also
showed jumping, which is a much more dramatic photosalient
phenomenon compared to the phenomena of 1o and 2o (Figure
S21, Movie S8). This is attributed to the large size changes from
3o to 3c compared with those of the other crystals (Figure 3).
Moreover, when irradiating UV light to 3o rod crystals,
photoinduced bending was observed with weak UV light and a
photosalient effect was observed with strong UV light, as with
the thin crystals (Figure 8). Specifically, the 3o rod crystal
showed bending when irradiated with weak UV light but
reversibly changed back to its original shape with irradiation by
visible light (observation of digital microscope: white light). The
reversible bending was successively controlled upon alternate
irradiation with the weak UV and visible lights (Figure S23). In
comparing the curvature on the crystal with weak and strong UV
light, the strong UV light produces bending in a short time than
does the weak UV light. With strong UV light, the crystal cracked
when it bent to about half of the maximum curvature value
reached by weak UV light (Movie S9). Therefore, photoinduced
bending and photosalient phenomena of the thin crystals of 3o
Conclusions
The photosalient phenomena of crystals found in three
diarylethenes were examined while focusing on the effect of
crystal size and UV intensity. Although the diarylethenes of 1o
and 2o have been previously investigated in detail, there has
been no report on the photosalient effect of their crystals.[12,17]
This is due to the fact that the photosalient effect was observed
only when strong UV light was irradiated. Consequently, it is
likely that a much wider class of crystals of diarylethenes may
show the photosalient effect upon irradiation with strong UV light.
This possibility should be carefully investigated not only for
application of the photosalient effect but also for our
understanding of the limitations of using the intensity of
UV/visible light in applying the bending phenomena.
For the bulk crystals prepared by recrystallization, UV-induced
peeling of the surfaces was observed. The peeling phenomena
appeared on the crystalline surfaces, so they were independent
of crystal sizes. On the other hand, the photosalient phenomena
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Figure 8. (a) Molecular packing of 3o. (b) Photoinduced bending of 3o rod crystal due to weak UV light (3o rod crystal: 2.29 × 0.132 × 0.0325 mm (length ×
width × thickness),  = 365 nm, 810 W cm-2). (c) Photosalient effect of 3o rod crystal due to strong UV light (3o rod crystal: 1.01 × 0.154 × 0.0351 mm
(length × width × thickness),  = 365 nm, 277 mW cm-2). (d) Change in the curvature with irradiation time: photoinduced bending of (b) (black circles) and
photosalient effect of (c) (red circles). Scale bars: 0.4 mm for (b), and 100 m for (c). Both (b) and (c) were irradiated from the b-axis direction.
of thin crystals prepared by sublimation did show the size
dependency. In particular, the photosalient phenomena of the
crystal of 3o showed dependence on thickness, i.e., thinner
crystals of 3o showed more remarkable photosalient
Acknowledgements
phenomena. As soon as UV light was irradiated, breaking and
jumping phenomena occurred. This finding is in contrast to the
Kono, and A. Nagai for their help for measurements of thin
observation that the thin crystal of 3o only showed bending with
The authors express thanks to A. Fujimoto, R. Nishimura, R.
crystals of 3o at a synchrotron radiation facility Spring-8, and are
coloration upon weak UV light irradiation. For a bulk crystal of 3o,
grateful
to
Zeon
Co.,
Ltd.,
for
providing
the
the crystal showed coloration upon weak UV irradiation, while
breaking occurred throughout the entire crystal. The crystal of
3o showed the most remarkable photosalient phenomena in its
ability to switch the photoresponse depending on the UV light
intensity. Recently, the application of the photosalient
phenomena has been reported for the hybrid material of an
electrical fuse link,[23] and for hollow-crystal scattering
inclusions.[24] In the near future, photosalient phenomena will be
given much more attention, and related applications could be
developed by effectively controlling these phenomena by light
intensity. We believe the current results provide an important
clue toward achieving this goal.
octafluorocyclopentene to synthesize the diarylethene
derivatives having perfluorocyclopentene moiety. This work was
supported by JSPS KAKENHI Grant Number JP26107012,
JP15H01096, and JP17H05272 in Scientific Research on
Innovative Areas “Photosynergetics” and the CREST program
(JPMJCR17N2) of the Japan Science and Technology Agency,
the Core-to-Core Program A. The synchrotron radiation
experiments were performed using the BL02B1, BL40B2 and
BL40XU beamlines of SPring-8 with the approval of the Japan
Synchrotron Radiation Research Institute (JASRI) (Proposal Nos.
2014B1213, 2015A1240, 2015B1215, 2018A1104, 2018A1208,
2018B1091, 2018B1092 and 2018B1674).
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Conflicts of interest
There are no conflicts of interest to declare.
Keywords: photochromism • diarylethene • crystal • photosalient
effect • asymmetric structure
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10.1002/chem.201900811
Chemistry - A European Journal
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Photosalient
phenomena
were
Y. Nakagawa, M. Morimoto,*
N. Yasuda, K. Hyodo, S. Yokojima,
S. Nakamura, K. Uchida*
observed on diarylethene crystals by
amplifying the UV incidence. The
patterns were dependent on the
molecular ordering.
Page No. – Page No.
Photosalient effect of diarylethene
crystals of thiazoyl and thienyl
derivatives
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