Novel spiropyran derivative based reversible photo-driven colorimetric and fluorescent probes for recognizing Fe3+, Cr3+ and Al3+ metal ions

Article abstract of DOI:10.1016/j.inoche.2020.107968

A novel spiropyran derivative, 3-(5-methoxy-6′-nitro-3H-spiro[benzo[d]thiazole-2,2′-chromen]-3-yl)propane-1-sulfonate (MO-SP) as a chemosensor for metal ions has been synthesized. The prepared MO-SP as a colorimetric and fluorescent sensor is sensitive to common trivalent metal ions (Al³⁺, Cr³⁺ and Fe³⁺). In addition, it can be used as a “naked eye” identification agent of Fe³⁺, Cr³⁺ and Al³⁺. When Fe³⁺, Cr³⁺ or Al³⁺ was added, the color changed from orange to yellow, meanwhile, the absorbance at the maximum absorption wavelength decreased obviously, but it did not change significantly when other metal ions were added. The MO-SP is proved to be sensitive, selective, good linear-relationship and low detection limit for recognition of Fe³⁺, Cr³⁺ and Al³⁺. Moreover, the MO-SP also could be employed as molecular logic function.

Full text of DOI:10.1016/j.inoche.2020.107968

InorganicChemistryCommunications117(2020)107968
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Inorganic Chemistry Communications
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Short communication
Novel spiropyran derivative based reversible photo-driven colorimetric and
fluorescent probes for recognizing Fe3+, Cr3+ and Al3+ metal ions
⁎
⁎
Minyan Huanga, Jintao Zhoua, Xudong Zhengc, Yuzhe Zhangc, Song Xua, , Zhongyu Lia,b,c,
a Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, PR China
b Jiangsu Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University, Changzhou 213164, PR China
c School of Environmental and Safety Engineering, Changzhou University, Changzhou 213164, PR China
G R A P H I C A L A B S T R A C T
A R T I C L E I N F O
A B S T R A C T
Keywords:
A novel spiropyran derivative, 3-(5-methoxy-6′-nitro-3H-spiro[benzo[d]thiazole-2,2′-chromen]-3-yl)propane-1-
sulfonate (MO-SP) as a chemosensor for metal ions has been synthesized. The prepared MO-SP as a colorimetric
and fluorescent sensor is sensitive to common trivalent metal ions (Al3+, Cr3+ and Fe3+). In addition, it can be
used as a “naked eye” identification agent of Fe3+, Cr3+ and Al3+. When Fe3+, Cr3+ or Al3+ was added, the
color changed from orange to yellow, meanwhile, the absorbance at the maximum absorption wavelength de-
creased obviously, but it did not change significantly when other metal ions were added. The MO-SP is proved to
Spiropyran derivative
Colorimetric chemosensor
Fluorescent chemosensor
Trivalent metal ions
be sensitive, selective, good linear-relationship and low detection limit for recognition of Fe3+, Cr3+ and Al3+
.
Moreover, the MO-SP also could be employed as molecular logic function.
1. Introduction
content of some metal ions such as Fe3+, Hg2+ and Cr3+ is high, it will
affect the metabolism of cells and injury some organs which will
eventually cause irreversible harm to our body [1–4]. In order to detect
In human life, metal ions can be seen everywhere, but when the
⁎ Corresponding authors at: Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University,
Changzhou 213164, PR China (Z. Li).
E-mail addresses: cyanine123@163.com (S. Xu), zhongyuli@mail.tsinghua.edu.cn (Z. Li).
https://doi.org/10.1016/j.inoche.2020.107968
Received 28 March 2020; Received in revised form 5 May 2020; Accepted 12 May 2020
Availableonline15May2020
1387-7003/©2020ElsevierB.V.Allrightsreserved.

M. Huang, et al.
InorganicChemistryCommunications117(2020)107968
and measure metal ions, researchers have made great efforts to develop
suitable chemical sensors [5–7]. These sensitivity and selectivity sen-
sors play an important role in the field of biological, medicinal and
environment researches.
of different ion complexes can be distinguished by comparison of
spectral behaviors, which is ionchromism [34–40].
In the present work, a novel spiropyran derivative, 3-(5-methoxy-6′-
nitro-3H-spiro[benzo[d]thiazole-2,2′-chromen]-3-yl)propane-1-sulfo-
nate (MO-SP) as a chemosensor for metal ions has been synthesized.
The as-prepared probe can effectively recognize the trivalent metal ions
(Cr3+, Al3+ and Fe3+). The MO-SP chemosensor can provide a broad
application prospect because of its good anti-interference capability,
excellent reversibility and low detection limit.
Transition metals and heavy metal elements are abundant in nature,
some of which play an exceedingly important role in life. For the past
few years, domestic and foreign research enthusiasm for trivalent metal
ions (M3+) is only increasing [8]. Chromium, one of the major pollu-
tants for environment, was produced by steelmaking industry, fossil
fuel combustion and paint industries, each of which delivers toxic in-
gredients into the soil and streams [9–11]. In addition, highly sensitive
Cr3+ can enter the body then bind to DNA and has harmful effects on
cell structure and cell composition [12]. Sorting the most abundant
elements in the current crust by quality, aluminum is the third, so it is
widely used in shipbuilding, aerospace equipment, corrosion resistant
containers and indoor sound insulation board [13–16]. The heavy use
of aluminum leads to increasing leakage into the environment, which
can be dangerous both in humans, animals and plants [17]. For in-
stance, health problems, such as neurological disorders, have also been
linked to the accumulation of Al3+ in brain tissue [18]. Iron-one of the
high content metals on Earth, plays the role of a catalyst to transport
oxygen in oxido-reductase reactions [19]. Either the excess or defi-
ciency may damage organisms and induce a variety of diseases such as
renal failure, cell death, cancer and Alzheimer [20–23]. Considering the
potential impact of M3+ on the environment and human survival, we
need to find appropriate methods to detect them effectively.
2. Experimental section
2.1. Reagents and materials
All raw materials and solvents are purchased and used without
further purification. Metal ion solution (1.0 × 10−2 M) was prepared
with pure water and nitrate (Ba2+, Pb2+, Ni2+, Al3+, Mg2+, Cr3+, K+
,
Na+, Fe3+, Zn2+, Cu2+, Ag+, Ca2+, Cd2+ and Co2+).
2.2. Synthesis of 3-(2-methyl-5-methoxybenzothiazole) propane-1-
sulfonate
The synthetic route of 3-(2-methyl-5-methoxybenzothiazole) pro-
pane-1-sulfonate is shown in Scheme 1. A 250 mL circular bottom flask
was taken and 2-methyl-5-methoxybenzothiazole (0.90 g, 0.005 mol)
was measured and dissolved in toluene (20 mL). After stirring for
30 min, 1, 3-propanolactone (1.00 g, 0.008 mmol) was added. The
reaction mixture was refluxed overnight. The precipitate produced was
filtered at room temperature and washed with acetone and ethyl
acetate and eventually dried to yield the white powder (84%), namely
intermediate. 1H NMR (400 MHz, DMSO‑d6) δ 8.25 (d, J = 9.0 Hz, 1H),
8.12 (s, 1H), 7.39 (d, J = 6.8 Hz, 1H), 4.92 (t, J = 8.2 Hz, 2H), 3.96 (s,
3H), 3.16 (s, 3H), 2.63 (t, J = 6.2 Hz, 2H), 2.22–2.09 (m, 2H).
Several methods for the determination and detection are reported
such as atomic absorption spectrometry with electrothermal (graphite
furnace) atomization (GF-AAS) [24–25] and inductively coupled
plasma optical emission spectrometry (ICP-OES) [26]. The advantages
of GF-AAS are high efficiency and good sensitivity, which can reach ppb
level, on the contrary, its disadvantages are large background inter-
ference and time consumption. ICP-OES can measure the amount of
elements in the sample but it is not economical and environmentally
friendly. The analytical methods based on UV–Visible spectro-
photometry and fluorescence spectroscopy are relatively real-time, in-
expensive and convenient, so they are valued and widely used.
Spiropyrans are one of the important photochromic compounds that
have attracted much interest from the viewpoints of both fundamental
elucidation of photochemical reactions [27,28] and their potential ap-
plication for optical devices and sensors [29–33]. The photochromism
of spiropyrans usually results from photo-cleavage of the C-O bond
under an irradiation, creating a ring-opened merocyanine form which
displays broad absorption in the visible region and which can be con-
verted back to the (colorless) ring-closed SP form by another irradia-
tion. With the in-depth study of photochromic spiropyrans, researchers
found that different external stimuli such as solvents, pH and ions have
different effects on the performance of spiropyrans. For example, the
choice of different solvents can cause reversible changes in the position
and intensity of the UV–Vis absorption spectrum of the compound,
which is called solvatochromism. In addition, spiropyran compounds
complexed with some ions to form relatively stable blue-shift metal
complexes, which are easily detected on the spectrum, and the stability
2.3. Synthesis of 3-(5-methoxy-6′-nitro-3H-spiro[benzo[d]thiazole-2,2′-
chromen]- 3-yl)propane-1-sulfonate (MO-SP)
The synthetic route of MO-SP is shown in Scheme 2. The above
intermediate product (0.30 g, 0.001 mol) was dissolved in ethanol
(20 mL) and then piperidine (0.09 g, 0.001 mol) was slowly added.
After constant stirring for
1 h, 5-nitro salicylaldehyde (0.16 g,
0.001 mol) was put in, the solution was refluxed for 18 h to produce a
red solution. The mixture was purified by column chromatography
(dichloromethane: methanol = 50:1) and obtained the red powder
(41%), namely MO-SP. 1H NMR (300 MHz, DMSO‑d6) δ 8.59–8.48 (m,
2H), 8.17–8.08 (m, 2H), 7.98 (d, J = 2.4 Hz, 1H), 7.84 (dd, J = 9.7,
3.1 Hz, 1H), 7.28 (dd, J = 9.0, 2.3 Hz, 1H), 6.31 (d, J = 9.7 Hz, 1H),
4.87 (t, J = 7.9 Hz, 2H), 3.95 (s, 3H), 2.68 (t, J = 6.3 Hz, 2H), 2.16 (q,
J = 8.2, 6.5 Hz, 2H). 13C NMR (75 MHz, DMSO‑d6) δ 179.42, 173.74,
161.12, 148.88, 143.26, 132.23, 132.03, 128.33, 124.91, 123.94,
121.29, 119.25, 117.27, 109.49, 100.24, 63.25, 56.93, 47.82, 24.64.
Scheme 1. Synthetic route of intermediate.
2

M. Huang, et al.
InorganicChemistryCommunications117(2020)107968
Scheme 2. Synthetic route of MO-SP.
water = 1:1, V/V) was deep red and the absorption spectrum showed a
prominent band at the visible region. While under visible condition, the
solution of MO-SP changed to pale red with a reduced absorption at
500 nm and a slight red-shift. This result indicated that MO-SP can be
transformed from its original open loop merocyanine (MC) structure to
the closed loop SP structure under visible light irradiation. However,
after 2 h of visible light exposure and 2 h of ultraviolet light exposure,
the absorption can rise somewhat, but lower than that in the dark. The
absorption peak of ultraviolet and visible light after cyclic irradiation at
500 nm showed that partial degradation occurred after the three cycles,
but the reproducibility was good (inset of Fig. 1).
3.2. Metal-induced recognition of MO-SP
In order to study the recognition of metal ions by MO-SP, various
cations such as Cd2+, Mg2+, Ni2+, Cu2+, Ca2+, Co2+, Fe3+, Al3+
,
Cr3+, Pb2+, Ag+, Na+, K+, Zn2+ and Ba2+ (1 × 10−2 M) were added
to the aqueous solution of spiropyran derivative (4 × 10−5 M, etha-
nol:water = 1:1, V/V). Fig. 2 shows the absorption and fluorescence
spectra of MO-SP after adding different cations. It was found that the
absorption of Fe3+/Cr3+/Al3+-MO-SP at 500 nm decreased sig-
nificantly while adding of other metal ions caused only negligible
changes in absorption spectra (Fig. 2A). Similarly, the solution changed
from orange to yellow when 0.05 mL of Fe3+/Cr3+/Al3+ was added
while the color of other metals did not change (Fig. S4). This result
demonstrated that MO-SP could be used as a colorimetric chemosensor
for M3+ (Fe3+/Cr3+/Al3+). As is shown in Fig. 2B, the intensity of
Al3+ varied the most, while that of Fe3+ and Cr3+ changed little. These
results manifest that MO-SP has a superb identification for Fe3+, Al3+
Fig. 1. Absorption and color changes after exposure to dark, Vis 2 h and Vis
2 h + UV 2 h. Inset: Cycle curves at different irradiations at 500 nm.
2.4. Characterization
1H NMR and 13C NMR spectra were recorded on Bruker Avance III
300 MHz or 400 MHz using tetramethylsilane (TMS) as an internal
standard and DMSO as solvent. The IR spectra were performed on a
Protégé 460 spectrometer using KBr disk. The fluorescence emission
spectra were recorded on a F-280 spectrometer. The absorption spectra
were measured by an UV-759 spectrophotometer.
and Cr3+
.
3. Result and discussion
The sensitivity of MO-SP was studied by titration experiment. Fig. 3
shows the effect of concentration of M3+ (Fe3+, Al3+ and Cr3+) on the
absorption of MO-SP (Fig. 3A, B and C). Fig. 3a, b and c) displays the
absorption wavelength diagram corresponding to each concentration at
the absorption wavelength of 500 nm. It can be found that with in-
creasing of the concentration of metal ion, the absorption at 500 nm
3.1. Photochromic behavior of MO-SP
Fig. 1 shows the photochromic performance of MO-SP. Before ir-
radiation, the color of the MO-SP solution (4 × 10−5 M, ethanol:
Fig. 2. Change of UV–Vis absorption (A) and fluorescent (B) of MO-SP (4 × 10−5 M, ethanol: water = 1:1, V/V) upon 0.05 mL addition of different metal ion
solutions (Pb2+, Na+, Ni2+, Fe3+, Mg2+, K+, Cd2+, Zn2+, Ag+, Ca2+, Ba2+, Cu2+, Co2+, Cr3+ and Al3+).
3

M. Huang, et al.
InorganicChemistryCommunications117(2020)107968
Fig. 3. Absorption spectra of the MO-SP solution (4 × 10−5 M, ethanol: water = 1:1, V/V) with increasing amounts of M3+ (1 × 10−2 M, in water). (A, a) Fe3+; (B,
b) Cr3+; (C, c) Al3+
.
MO-SP+M
MO-SP+M
0.6
0.4
0.2
0.0
B
A 0.6
MO-SP+M+Cr3+
MO-SP+M+Fe3+
0.4
0.2
0.0
Ba2+ Na+ Ca2+ Cd2+ Zn2+ Co2+ K+ Ag+ Pb2+ Ni2+ Mg2+ Cu2+ None
Ba2+ Na+ Ca2+ Cd2+ Zn2+ Co2+ K+ Ag+ Pb2+ Ni2+ Mg2+ Cu2+ None
MO-SP+M
MO-SP+M+Al3+
0.6
C
0.4
0.2
0.0
Ba2+ Na+ Ca2+ Cd2+ Zn2+ Co2+ K+ Ag+ Pb2+ Ni2+ Mg2+ Cu2+ None
Fig. 4. Competitive selectivity study of M3+-MO-SP complex in the presence of excess amounts of different metal ions (1 × 10−2 M, in water). (A) Fe3+-MO-SP; (B)
Cr3+-MO-SP; (C) Al3+-MO-SP.
decreased ratio-metrically and then gradually reached steady. This re-
sult suggested that there was an equilibrium relationship between MO-
SP and M3+ (Fe3+/Cr3+/Al3+) complex. In order to prove the above
conclusion, the fluorescence titration experiment was performed. As
shown in Fig. S5, the fluorescence result of MO-SP is similarly in ac-
cordance with absorption of MO-SP.
3.3. Competitive selectivity for detecting M3+ (Fe3+, Al3+ and Cr3+) in the
presence of other metal ions
The competitive selectivity of MO-SP towards M3+ was studied
when the interference of various monovalent or divalent metal ions
were added. The absorption spectra of MO-SP (4 × 10−5 M, ethanol:
4

M. Huang, et al.
InorganicChemistryCommunications117(2020)107968
Fig. 5. Linear relationship between the absorption of MO-SP at 500 nm and the
Fig. 7. Change of absorbance of MO-SP when M3+ and EDTA are added al-
concentration of M3+ (A) Fe3+, (B) Cr3+ and (C) Al3+
.
ternately. (1: Fe3+/Cr3+/Al3+ 2: EDTA).
water = 1:1, V/V) were used to investigate its sensitivity in aqueous
solutions with different interfering ions (1 × 10−2 M) coexisting with
Fe3+, Al3+ or Cr3+ (1 × 10−2 M). It was found that after adding other
metal ions, the absorbance of MO-SP did not change significantly
(Fig. 4), indicating the established chemosensing process is completely
unaffected by other metal ions. Moreover, as shown in Fig. S6, though
there were some intensity fluctuations in the fluorescence spectra, it
can also conclude the stability of MO-SP in the presence of other metal
ions.
3.5. Reversibility of MO-SP
Reversibility is also an effective indicator to evaluate the chemo-
sensor performance of MO-SP. As can be seen from the Fig. 7, after the
addition of M3+ (Fe3+/Cr3+/Al3+) and EDTA alternately, the absorp-
tion changes at 500 nm were observed. It can be found that Fe3+, Al3+
and Cr3+ can all be invertible three times. This result indicated that the
sensor of MO-SP had great stability and repetition. The reason for the
incomplete recovery of the reversible curve is that the number of mo-
lecules with reverse-photochromic ability gradually decreases or even
completely loses its reversible property due to oxidation decomposition
during the cyclic process of repeated discoloration and fading of pho-
tochromic materials.
3.4. Detection limit and response time
Fig. 5A–C show the linear relationship between the absorption of
MO-SP at 500 nm and the concentration of Fe3+ in the range of
0.1–2.1 μM, Cr3+ in the range of 0.1–2.2 μM, Al3+ in the range of
0.1–2.4 μM, respectively. The detection limits of Fe3+, Cr3+ and Al3+
are calculated to be 4.56 μM, 4.39 μM and 4.89 μM, respectively. This
result indicated that MO-SP can be used as a highly selective recogni-
3.6. Possible complexation mechanism of MO-SP-M3+
Fig. 8A shows the infrared spectra of MO-SP in the presence and
absence of M3+. The characteristic absorption wavenumber of C-N
bond at 1420 cm−1 was shifted to 1384 cm−1 after M3+ (Fe3+, Al3+
and Cr3+) was added. Similarly, the absorption wavenumber of C-S-C
was shifted from 1240 cm−1 to 1230 cm−1, suggesting that C-S-C and
C-N of MO-SP were involved in the recognition of M3+. To further
confirm this conclusion, 1H NMR spectra of MO-SP in the presence and
absence of M3+ were performed. In Fig. 8B, the proton (Ha, Hb) of MO-
SP was 6.3 ppm and 4.8 ppm, while after adding M3+ (Fe3+, Al3+ and
Cr3+), the Ha and Hb were offset to the lower field, which verified that
N-M3+-S coordination occurred.
tion sensor of Fe3+, Cr3+ and Al3+
.
It is acknowledged that the response time is one of the important
factors to evaluate chemosensor performance. After 0.05 mL Fe3+
/
Cr3+/Al3+ was added to MO-SP (4 × 10−5 M) solution, the absorption
at 500 nm gradually decreased in 0–400 s and changed almost stable
after 400 s (Fig. 6). It can be found that the response time of MO-SP to
Fe3+/Cr3+/Al3+ is short and the corresponding performance is good.
It is well known that the complex curve of chemosensor and the
metal ion allows us to know their binding ratio, and the highest point of
the complex curve corresponds to their binding ratio [41]. As seen from
Fig. S7, Job’s plot shows that the absorption of Fe3+/Cr3+/Al3+ at 0.6/
0.4/0.6 mol fraction absorbance reach maximum. These data indicate
that the chemometrics of Fe3+/Cr3+/Al3+ -MO-SP complexes are
about 2:1,1:2 and 2:1, respectively. Therefore, the chemosensor me-
chanism between MO-SP and M3+ (Fe3+/Cr3+/Al3+) can be proposed
based on the analysis of Job’s plot, IR and 1H NMR (Scheme 3).
3.7. Application of MO-SP in molecular logic gate
In recent years, the application of molecular logic gates has become
a hot topic [42,43]. The gate seems to be a simple switch, but can be
used for the signal amplification and transduction, which is a very
meaningful research. As seen from Fig. 9, M3+ (Fe3+, Cr3+ and Al3+
)
Fig. 6. Absorbance of MO-SP (4.0 × 10−5 M) at 500 nm after adding M3+ (A)
and chelating agent EDTA were taken as the input signal, and the ab-
sorption change at 500 nm was taken as the output signal. The
Fe3+, (B) Cr3+, and (C) Al3+ for a period of time.
5

M. Huang, et al.
InorganicChemistryCommunications117(2020)107968
Hb
Ha
Fig. 8. (A) FT-IR spectra of MO-SP and MO-SP -M3+. (B) 1H NMR spectra of MO-SP and MO-SP -M3+.
Scheme 3. Possible complexation mechanism.
6

M. Huang, et al.
InorganicChemistryCommunications117(2020)107968
Fig. 9. (a) Truth table, (b) INHIBIT logic circuit based on M3+ and EDTA as chemical inputs and absorbance mode as output.
occurrence of the absorbance at 500 nm depends on the complex of
MO-SP and M3+, and the absorbance at 500 nm increased when EDTA
was added to the solution. Only when M3+ (Fe3+, Cr3+ and Al3+) was
used as input, the value of output for the absorbance at 500 nm is 1.
While in other cases, the value is 0. Therefore, it is practical to apply the
recognition of MO-SP to M3+ to circuit elements with memory and
erase functions.
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In summary, a novel spiropyran derivative, 3-(5-methoxy-6′-nitro-
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(MO-SP) as a chemosensor has been synthesized. The prepared MO-SP
can be used as a colorimetric and fluorescent sensor to selectively detect
common trivalent metal ions (Al3+, Cr3+ and Fe3+) in ethanol and
water solutions. The chelated of MO-SP-M3+ can be converted to the
original form of spiropyran by the irradiation and EDTA. Therefore, this
chemosensor provided a reversible optical-driven and chemistry-driven
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Declaration of Competing Interest
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Acknowledgements
This work was financially supported by the National Natural Science
Foundation of China (No. 21876015).
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