Photochromism of a novel asymmetrical diarylethene with a (formyloxyethoxy)ethyl-linked naphthalimide moiety

Article abstract of DOI:10.1002/poc.3336

A novel asymmetrical diarylethene with a (formyloxyethoxy)ethyl-linked naphthalimide unit was synthesized, and its photochromic and fluorescence properties were systematically investigated in both solution and a poly(metyl methacrylate) film. The diarylethene showed significant photochromism and notable fluorescence switching properties upon irradiation with ultraviolet/visible light. Compared with the parent diarylethene, introduction of the naphthalimide moiety was effective to increase the molar absorption coefficient, the fluorescence quantum yield, and fluorescent modulation efficiency of the diarylethene. Copyright

Full text of DOI:10.1002/poc.3336

Research Article
Received: 16 March 2014,
Revised: 23 June 2014,
Accepted: 25 June 2014,
Published online in Wiley Online Library: 4 August 2014
(wileyonlinelibrary.com) DOI: 10.1002/poc.3336
Photochromism of a novel asymmetrical
diarylethene with a (formyloxyethoxy)ethyl-
linked naphthalimide moiety
Xue Lia, Gang Liua and Shouzhi Pua*
A novel asymmetrical diarylethene with a (formyloxyethoxy)ethyl-linked naphthalimide unit was synthesized, and its photochro-
mic and fluorescence properties were systematically investigated in both solution and a poly(metyl methacrylate) film. The
diarylethene showed significant photochromism and notable fluorescence switching properties upon irradiation with
ultraviolet/visible light. Compared with the parent diarylethene, introduction of the naphthalimide moiety was effective to in-
crease the molar absorption coefficient, the fluorescence quantum yield, and fluorescent modulation efficiency of the diarylethene.
Copyright © 2014 John Wiley & Sons, Ltd.
Keywords: diarylethene; fluorescence switch; naphthalimide; photoirradiaton; photochromism
as a donor in photochromic fluorescence resonance energy
transfer (pcFRET); the fluorescent emission of the donor was
INTRODUCTION
Photochromic compounds have attracted tremendous atten-
tion because of their wide applications in optical memory
media and photooptical switching devices.[1,2] Among various
types of photochromic compounds, diarylethenes with hetero-
cyclic aryl rings are the most promising candidates for photo-
electronic applications because of their excellent thermal
stability, notable fatigue resistance, rapid response, and high
reactivity in solid state.[3–6]
To date, the molecular skeletons mainly focus on exploitation
of the central ethene bridge and introduce heterocyclic aryl rings
with different substituents. For instance, the central ethene
bridge has been confined to a cyclopentene unit[7] or its strong
electron-withdrawing analogs, such as perfluorocyclopentene,[8]
maleic anhydride,[9] and maleic imide.[10,11] More recently,
several groups have successfully synthesized novel diarylethenes
with new rings as a central bridge to perform photochromism.[12,13]
Owing to the structural changes of diarylethenes upon photo-
chromic reaction, numerous efforts have been undertaken for the
synthesis of diarylethene derivatives with a range of heteroaryl
units, such as thiophene,[14,15] benzothiophene,[16] furan,[17]
benzofuran,[18] thiazole,[19] indole,[20,21] pyrazole,[22] and pyrrole
rings.[23]
In recent years, much effort has been focused on designing and
synthesizing fluorescent diarylethene derivatives by introducing
one or more fluorescent moieties.[24–28] Among the fluorophores,
a naphthalimide unit has attracted much research interest because
of its unique photophysical properties.[29,30] Its absorption and fluo-
rescence emission spectra lie within the ultraviolet (UV) and visible
(vis) regions, and the various photophysical properties can be easily
tuned through skillful structural design. The versatility of the struc-
ture resulted from either the aromatic “naphthalene” moiety or the
“N-imide site”. Consequently, the 1,8-naphthalimide derivatives
have been extensively used as strongly absorbing and colorful dyes
in the field of anion recognition and sensing.[31,32] Recently, 1,8-
naphthalimide has been introduced to the diarylethene sys-
tems.[33–35] For instance, Irie et al.[33] developed the naphthalimide
modulated by cyclical transformations of the photochromic
acceptor. Tian et al.[34] reported novel diarylethenes containing
naphthalimide as the center ethene bridge that exhibited
considerably high cyclization quantum yield and good fatigue
resistance. Yi et al.[35] studied the switchable supramolecular
self-assemblies on the basis of the interaction between a mela-
mine group containing a photochromic diarylethene unit and
naphthalimide derivate. Both the absorption and fluorescence
spectra of the assembly can be reversibly switched by alter-
nating UV/Vis light irradiation. The valuable achievements were
helpful for us to explore the character of diarylethene deriva-
tives labeled with a naphthalimide moiety. Moreover, benzo-
furan is a fascinating aryl because of its relative lower aromatic
stabilization energy that can be potential to improve the ther-
mal stability of the closed-ring isomers of diarylethenes.[36] In
this study, a novel diarylethene, 1-(2-methyl-3-benzofuryl)-2-
{2-methyl-5-{4-[N-(2-(2-formyloxyethoxy)ethyl)naphthalimide]
phenyl}-3-thienyl}perfluorocyclopentene (1o), was synthesized.
In the molecule, 2-methylbenzofuran is selected as one of the
two aryl groups, and naphthalimide occupies a fluorescent
group. In order to evaluate the effect of the naphthalimide on
the photochromic behavior, 1-(2-methyl-3-benzofuryl)-2-[2-
methyl-5-(4-formylphenyl)-3-thienyl]perfluorocyclopentene
(2o) is synthesized as a model compound. Their photochromism
and fluorescence in both solution and poly(metyl methacrylate)
(PMMA) amorphous films were studied. The photochromic pro-
cesses of diarylethenes 1 and 2 are shown in Scheme 1.
* Correspondence to: S. Z. Pu, Jiangxi Key Laboratory of Organic Chemistry,
Jiangxi Science and Technology Normal University, Nanchang 330013, China.
E-mail: pushouzhi@tsinghua.org.cn
a X. Li, G. Liu, S. Z. Pu
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology
Normal University, Nanchang 330013, China
J. Phys. Org. Chem. 2014, 27 764–769
Copyright © 2014 John Wiley & Sons, Ltd.

DIARYLETHENE WITH A NAPHTHALIMIDE FLUOROPHORE
in both methanol (2.0 × 10À5 mol LÀ1) and
PMMA films. As shown in Fig. 1(A), the absorp-
tion maximum of compound 1o was observed
at 317 nm (ε, 3.69 × 104 L molÀ1 cmÀ1) in meth-
anol. Upon irradiation with 313 nm light, the
colorless solution of 1o turned violet with the
emergence of a new vis absorption band cen-
tered at 535 nm (ε, 1.84 × 104 L molÀ1 cmÀ1),
which could be attributed to the closed-ring
form 1c. The violet solution became colorless
upon irradiation with vis light (λ > 450 nm),
indicating that 1c returned to its initial form
1o. The absorption spectral change was accom-
panied by a clear isosbestic point that was
observed at 342 nm. In order to clarify the
Scheme 1. Photochromism of diarylethenes 1o and 2o
difference between the diarylethenes with or
without the fluorescent dye, the photochro-
RESULTS AND DISCUSSION
mism of 2o was studied under the same conditions. The absorp-
tion spectral changes of 2o induced by photoirradiation in
methanol are shown in Fig. 1(B). In methanol, the open-ring isomer
of diarylethene 2o was 326 nm (ε, 2.91× 104 L molÀ1 cmÀ1).
Irradiation 2o with 313 nm light, a new absorption band centered
at 537 nm (ε, 1.64 × 104 L molÀ1 cmÀ1) because of the formation
of 2c, accompanied with a color change from colorless to violet.
The photoconversion ratios of 1 and 2 in the photostationary state
were determined using analytical HPLC, and the results are shown
in Fig. 2. It was calculated that the photoconversion ratios were
93% for 1 and 88% for 2, respectively.
Synthesis of diarylethene
The synthetic route to the target compound is shown in
Scheme 2. Diarylethene 2o was prepared by the reported
method.[37] Compounds 3 and 5 were then synthesized by Jones
oxidation[38] and acylation reaction,[39] respectively. Finally,
diarylethene 1o was synthesized by the esterification reaction
of 3 with 5. The structure of diarylethene 1o was confirmed by
mass spectrum, nuclear magnetic resonance (NMR) spectros-
copy, elementary analysis, and infrared spectroscopy.
The cyclization/cycloreversion quantum yields of 1 and 2 were
measured and summarized in Table 1. 1,2-Bis(2-methyl-5-phenyl-
3-thienyl)perfluorocyclopentene[40] was used as a reference for
the cyclization and the cycloreversion reactions. The standard
deviation of the experimental error is 4%. The cyclization
Photochromism
Diarylethenes 1 and 2 showed reversible color and absorption
spectrum changes upon alternating irradiation with UV/Vis light
Scheme 2. Synthetic route for diarylethenes 1o
Figure 1. Absorption spectra and color changes of diarylethenes 1o and 2o by irradiation in methanol (2.0 × 10À5 mol LÀ1) at room temperature: (A) 1o
and (B) 2o
J. Phys. Org. Chem. 2014, 27 764–769
Copyright © 2014 John Wiley & Sons, Ltd.
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X. LI, G. LIU AND S. PU
and 2c. The result was in good agreement with that of the
reported diarylethenes.[42–44] The reason may be attributed to
the polar effect of the polymer matrix and stabilization of molec-
ular arrangement in solid media.[45]
Fatigue resistance of diarylethenes is also critical to the practi-
cal applications in optical devices.[1,46] The fatigue resistance of 1
was examined in both methanol and a PMMA film (Fig. 4(A) and
4(B)) with alternating UV/Vis irradiation in the air at room tem-
perature. After repeating 10 coloration/decoloration cycles, no
obvious degradation was detected by UV/Vis absorption spec-
troscopy. The result indicated that 1c showed remarkable fatigue
resistance in solution. Moreover, the thermal stability of the
open-ring and closed-ring isomers of 1 was examined in metha-
nol at room temperature and 65 °C. At room temperature, storing
the solution in the dark for more than 10 days, no change
was observed in the UV/Vis spectra. When the methanol
solution containing 1 was heated under reflux (65 °C) for more
than 4 days in darkness, no decomposition was detected by
UV/vis spectroscopy.
Figure 2. Photoconversion ratios of 1o and 2o in the photostationary
state by HPLC method: (A) 1o and (B) 2o
quantum yield of 1 is higher than that of 2, whereas its
cycloreversion quantum yield is lower than that of 2. As can
also be seen from the data in Table 1, the absorption maxima
(λmax), molar absorption coefficient, and photoconversion ratio
were obviously different. The naphthalimide moiety was effec-
tive to increase the molar absorption coefficient and the
photoconversion ratio.
Fluorescence switching property
For practical applications in optical devices, it is important that
the photochromic materials can maintain good photochromism
in solid supports such as PMMA films.[41] 1 and 2 showed similar
photochromism in PMMA films as observed in methanol (Fig. 3).
Irradiation of 1o/PMMA film with 313 nm UV light resulted in the
appearance of a new absorption band at 542 nm, accompanied
with a color change from colorless to violet. The maximum ab-
sorption peak of 2c/PMMA was at 544 nm. Compared with those
in methanol, the absorption maxima of the closed-ring isomers
in PMMA films were bathochromic shifted by 7 nm for both 1c
The fluorescence properties of 1o and 2o in methanol
(2.0 × 10À5 mol LÀ1) and PMMA films (10% w/w) were measured
at room temperature. In methanol, the emission peaks of 1o
and 2o appeared at 392 and 445 nm when excited at 348 and
295 nm light, respectively. Choice of anthracene in acetonitrile
(Φf = 0.27) as a reference, the fluorescence quantum yields of
1o and 2o were 0.028 and 0.005 with 5% experimental error,
respectively. Like the reported diarylethenes,[47,48] 1o and 2o
exhibited remarkable fluorescence switching properties in
methanol during the photoisomerization. Upon irradiation with
Table 1. Photoreaction parameters of 1 and 2 in methanol (2.0 × 10À5 mol LÀ1
)
Compds
λ
o,max /nma (ε LÀ1 molÀ1 cmÀ1
)
λ
c,max /nmb (ε LÀ1 molÀ1 cmÀ1
Methanol PMMA film
)
Φc
PRd
Methanol
PMMA film
Φo-c
Φc-o
1
2
317 (3.69 × 104)
326 (2.91 × 104)
319
331
535 (1.84 × 104)
537 (1.64 × 104)
542
544
0.39
0.36
0.01
0.04
93%
88%
*Standard deviation of the experimental error: 4%.
aAbsorption maxima of open-ring forms.
bAbsorption maxima of closed-ring forms.
cQuantum yields of cyclization reaction (Φo-c) and cycloreversion reaction (Φc-o), respectively.
dPhotoconversion ratios of 1 and 2 (PR%) in the photostationary state.
Figure 3. Absorption spectra and color changes of diarylethenes 1o and 2o by irradiation in PMMA films (10% w/w) at room temperature: (A) 1o and (B) 2o
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J. Phys. Org. Chem. 2014, 27 764–769

DIARYLETHENE WITH A NAPHTHALIMIDE FLUOROPHORE
313 nm UV light, the emission
intensity of 1o and 2o de-
creased obviously. The back
irradiation with appropriate
vis light regenerated the
open-ring isomers and recov-
ered the original emission
intensity. When it arrived at
the photostationary state, the
emission intensity of 1o and
2o was quenched to ca 20
and 40% (shown in Fig. 5),
respectively. The reversible
Figure 4. Fatigue resistance of 1 in both methanol and a PMMA film
fluorescence
quenching
mechanism of 1o and 2o is
different. The fluorescence
quenching of 2o was ascribed
to the enlargement of π-
electron
delocalization[1,2]
,
while that of 1o was ascribed
to the intramolecular energy
transfer.[49,50] The N-alkyl-
substituted 1,8-naphthalimide
derivative emits fluorescence
at
a
short wavelength.[51]
When diarylethene 1 is in the
open-ring form (λmax = 317
nm, in methanol), the 1,8-
naphthalimide unit emits fluo-
rescence because the energy
state of the diarylethene unit
is higher than the fluorescent
state. However, when it is in
Figure 5. Emission intensity changes of diarylethenes 1o and 2o upon irradiation with 313 nm light in meth-
anol (2.0 × 10À5 mol LÀ1) at room temperature: (A) 1o and (B) 2o
the closed-ring isomer (λmax
=
542 nm, in methanol) upon
irradiation with UV light, its
energy state is lower than the
fluorescent state. As a result,
the fluorescence of the 1,8-
naphthalimide unit is efficiently
quenched. In PMMA films, the
emission peaks of 1o and 2o
were observed at 416 and
425 nm when excited at 281
and 290-nm light, respectively.
The emission intensity changes
induced by photoirradiation of
1 and 2 in PMMA films are
shown in Fig. 6. Compared with
those in methanol, the emission
peaks in PMMA films had an
obvious red shift of 24 nm for
1 and a hypochromatic shift of
20 nm for 2. The fluorescent
intensity was quenched to 17%
for 1 and 21% for 2. As de-
scribed previously, the fluores-
cent modulation efficiency of 1
was greater than that of the
parent diarylethene 2 in both
methanol and PMMA films,
Figure 6. Emission intensity changes of diarylethenes 1o and 2o upon irradiation with 313 nm light in PMMA
films (10% w/w) at room temperature: (A) 1o and (B) 2o
Figure 7. Fluorescent switch cycles of diarylethene 1o: (A) in methanol and (B) in a PMMA film
J. Phys. Org. Chem. 2014, 27 764–769
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X. LI, G. LIU AND S. PU
calcd for C26H16F6O3S (%): C, 59.77, H, 3.09, and O, 9.19; found C, 59.71,
H, 3.14, and O, 9.16.
indicating that introduction of naphthalimide to the diarylethene
was effective to enhance the emission intensity, fluorescent
modulation efficiency, and fluorescence quantum yield.
As shown in Fig. 7, the fluorescent switch had good reversibil-
ity with alternating UV (313 nm) and visible light (>450 nm)
irradiation for more than 10 cycles. The reversible changes can
be used in a repeated “write-erase” process.[52]
N-[2-(2-Hydroxyethoxy)ethyl]naphthalimide (5)
To a stirred ethanol solution of 4 (0.40 g, 2.00 mmol), dropwise 2-(2-
aminoethoxy)ethanol (0.32 mL, 3.20 mmol) was added in ethanol
(15 mL) in a single-necked flask; the mixture was heated to reflux for
4 h. After being cooled down to room temperature, the solvent was
removed under reduced pressure. The solid was purified through flash
column chromatography to obtain a white solid 5 (0.49 g, 85% yield).
M.p. 114–115 °C. 1H NMR (400 MHz, DMSO-d6), δ (ppm): 3.89–3.94
(m, 4H, -CH2CH2-), 4.44–4.50 (m, 4H, -CH2CH2-), 4.55 (s, 1H, -OH), 7.98
(t, 2H, J = 8.0 Hz, naphthyl-H), 8.56 (d, 2H, J = 8.0 Hz, naphthyl-H), and
8.59 (d, 2H, J = 8.0 Hz, naphthyl-H); 13C NMR (DMSO-d6, 100 MHz, TMS):
39.63, 61.48, 67.84, 72.46, 123.73, 125.61, 128.46, 137.73, 137.94, 130.76,
and 159.54; HRMS (ESIÀ): m/z: calcd for C16H15NO4, 285.1001; found
285.0992; anal. calcd for C16H15NO4 (%): C, 67.36, H, 5.30, N, 4.91, and
O, 22.43; found C, 67.41, H, 5.34, N, 5.02, and O, 22.51.
CONCLUSIONS
In conclusion,
a novel fluorescent diarylethene with a
(formyloxyethoxy)ethyl-linked naphthalimide unit was synthe-
sized, and the effect of the naphthalimide moiety on the photo-
chromism and fluorescence was studied. Although the
naphthalimide moiety is effective to enhance the fluorescence
quantum yield, there is no substantial overlap between the
naphthalimide emission spectrum and the absorption spectrum of
the open-ring and closed-ring isomers of the diheteroarylethene.
As a result, diarylethene as an acceptor in pcFRET was not realized.
Further studies on the FRET principle are now in progress.
1-(2-Methyl-3-benzofuryl)-2-{2-methyl-5-{4-[N-(2-(2-
formyloxyethoxy)ethyl)naphthalimide]phenyl}-3-thienyl}
perfluorocyclopentene (1o)
To
compounds 5 (0.13g, 0.45mmol) and 3 (0.18 g, 0.35 mmol), 1-ethyl-3-(3-
dimethylaminopropyl)carbodiimide (0.87 g, 0.45 mmol),
a stirred anhydrous N,N-dimethylformamide (3 mL) solution of
EXPERIMENTAL SECTION
General
hydroxybenzotriazole (0.61mg, 0.45mmol), and triethylamine (60μL) were
added. The mixture was stirred at 20°C for 3h under nitrogen, and then,
it was concentrated, diluted with 5% of K2CO3 (aqueous), and extracted
with ethyl acetate. The combined organic layer was dried with MgSO4, fil-
tered, and evaporated. The crude product was purified by silica gel column
chromatography using petroleum ether/ethyl acetate (v/v = 2/1) as the elu-
ent to yield 1o (0.10g, 36%) as a white solid. M.p. 145–146 °C. 1H NMR
(CDCl3, 400 MHz), δ (ppm): 1.92 (s, 3H, -CH3), 2.15 (s, 3H, --CH3), 3.89–3.94
(m, 4H, -CH2CH2-), 4.44–4.50 (m, 4H, -CH2CH2-), 7.23 (s, 1H, thienyl-H),
7.25–7.29 (m, 2H, benzofuryl-H), 7.39 (d, 1H, J = 8.0Hz, benzofuryl-H), 7.43
(d, 1H, J= 8.0Hz, benzofuryl-H), 7.47 (d, 2H, J = 8.0Hz, phenyl-H), 7.68–7.72
(t, 2H, J= 8.0, naphthyl-H), 7.86 (d, 2H, J= 8.0, phenyl-H), 8.16 (d, 2H,
J= 8.0Hz, naphthyl-H), and 8.54 (d, 2H, J = 8.0Hz, naphthyl-H); 13C NMR
(CDCl3, 100 MHz), δ (ppm): 13.36, 14.84, 39.10, 64.14, 68.08, 68.58, 105.44,
111.10, 119.95, 122.56, 123.67, 124.65, 125.01, 126.01, 126.19, 126.88,
128.21, 129.15, 130.30, 131.29, 131.57, 133.89, 137.13, 141.09, 142.70,
154.19, 156.15, 164.25, and 165.87; IR (KBr, v, cmÀ1): 344, 747, 781, 896,
837, 989, 1067, 1093, 1123, 1274, 1273, 1333, 1344, 1662, 1714, and
2864; HRMS (ESIÀ): m/z: calcd for C42H29F6NO6S 789.1620; found
788.1622; anal. calcd for C42H29F6NO6S (%): C, 63.88, H, 3.70, N, 1.77, and
O, 12.16; found C, 63.82, H, 3.73, N, 1.79, and O, 12.15.
Nuclear magnetic resonance spectra were recorded on a Bruker AV400
(400 MHz) spectrometer with CDCl3 as the solvent and TMS as an internal
standard. Melting points were measured on a WRS-1B melting point
apparatus. UV/Vis spectra were recorded on a PerkinElmer Lambda 900
spectrometer. Photoirradiation was carried out with an SHG-200 UV
lamp, a CX-21 ultraviolet fluorescence analysis cabinet, and a BMH-250
vis lamp. Radiation of appropriate wavelength was isolated by different
light filters. Luminescence spectra were measured on a Hitachi 4600 fluo-
rescence spectrophotometer (the widths of the emission slit were se-
lected 5.0 and 5.0 nm). The fluorescence quantum yield measurement
was measured by excitation of the respective diarylethene (absorbance
at 0.05) and compared with the emission of anthracene in acetonitrile
(standard, Φf = 0.27). All solvents used were of spectrograde and were
purified by distillation prior to use. All reagents were obtained from
J&K Scientific Ltd without further purification. The PMMA films were pre-
pared by first dissolving 10-mg diarylethene sample and 100 mg PMMA
in chloroform (1 mL) with the aid of ultrasound; then, the homogeneous
solution was spin coated on a quartz substrate (10 × 10 × 1 mm).
1-(2-Methyl-3-benzofuryl)-2-[2-methyl-5-(4-carboxyphenyl)-
3-thienyl]perfluorocyclopentene (3)
Acknowledgements
To a stirred acetone (50 mL) solution of 2o (0.34 g, 0.66 mmol), dropwise
Jones reagent that was prepared from CrO3 (0.13 g, 1.29 mmol), H2SO4
(0.09 mL), and H2O (3.00 mL) was added. The mixture was further stirred
overnight. The reaction mixture was extracted with ether, and the or-
ganic layer was washed with brine, dried over MgSO4, filtered, and evap-
orated. The crude product was purified by silica gel column
chromatography (dichloromethane) to yield 3o (0.25 g, 74%) as a white
powder. M.p. 208–209 °C. 1H NMR (CDCl3, 400 MHz), δ (ppm): 1.91 (s,
3H, -CH3), 2.14 (s, 3H, -CH3), 6.78 (s, 1H, thienyl-H ), 7.20–7.24 (m, 1H,
benzofuryl-H), 7.26–7.31 (m, 1H, 1H, benzofuryl-H), 7.43 (d, 1H,
J = 8.0 Hz, benzofuryl-H), 7.49 (d, 1H, J = 8.0 Hz, benzofuryl-H), 7.64 (d,
2H, J = 8.0 Hz, phenyl-H), and 8.12 (d, 2H, J = 8.0 Hz, phenyl-H); 13C NMR
(CDCl3, 100 MHz, tetramethylsilane (TMS)): 13.36, 14.84, 107.74, 111.56,
117.23, 121.01, 121.86, 122.63, 123.04, 123.36, 124.24, 124.69, 127.44,
130.29, 130.84, 135.92, 136.05, 136.67, 138.43, 139.04, 154.73, and
169.04; high-resolution mass spectrometry (HRMS) (electrospray ioniza-
tion (ESIÀ): m/z: calcd for C26H16F6O3S: 522.0724; found 521.0717; anal.
This work was supported by the National Natural Science
Foundation of China (21162011, 21262015, and 51373072), the
Science Funds of Natural Science Foundation of Jiangxi Province
(20122BAB213004 and 20132BAB203005), and the Project of
the Science Funds of Jiangxi Education Office (KJLD12035
and GJJ12587).
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