A highly selective fluorescent chemosensor for Mg2+ based on a diarylethene with a quinoxaline unit

Article abstract of DOI:10.1002/poc.4030

A new fluorescent probe 1O was synthesized through linking diarylethene and Quinoxaline-2-hydraqzide group, probe 1O showed a selective “off-on” fluorescent response toward Mg²⁺. In the presence of Mg²⁺, the probe 1O displayed a distinct change of fluorescence color, from dark to green, the fluorescence intensity increased 6.8-fold, and meanwhile, emission peak has a significant blue shift, which was shifted from 524 nm to 518 nm. Then, on account of the fluorescence properties of compound 1O, we designed a logic gate. On top of that, probe 1O also can be successfully used to monitor Mg²⁺ of the actual water samples.

Full text of DOI:10.1002/poc.4030

Received: 18 July 2019
DOI: 10.1002/poc.4030
Revised: 31 August 2019
Accepted: 10 October 2019
R E S E A R C H A R T I C L E
A highly selective fluorescent chemosensor for Mg2+ based
on a diarylethene with a quinoxaline unit
Yaping Zhang | Hui Li
| Duohua Jiang | Shouzhi Pu
Jiangxi Key Laboratory of Organic
Chemistry, Jiangxi Science and
Technology Normal University,
Nanchang, China
Abstract
A new fluorescent probe 1O was synthesized through linking diarylethene and
Quinoxaline‐2‐hydraqzide group, probe 1O showed a selective “off‐on” fluores-
cent response toward Mg2+. In the presence of Mg2+, the probe 1O displayed a
distinct change of fluorescence color, from dark to green, the fluorescence
intensity increased 6.8‐fold, and meanwhile, emission peak has a significant
blue shift, which was shifted from 524 nm to 518 nm. Then, on account of
the fluorescence properties of compound 1O, we designed a logic gate. On
top of that, probe 1O also can be successfully used to monitor Mg2+ of the
actual water samples.
Correspondence
Hui Li, and Shouzhi Pu, Jiangxi Key
Laboratory of Organic Chemistry, Jiangxi
Science and Technology Normal
University, Nanchang 330013, China.
Email: lihui5626@163.com;
pushouzhi@tsinghua.org.cn
Funding information
the National Natural Science Foundation
of China, Grant/Award Numbers:
21861017, 41867052 and 41867053; the
Open Project Program of “311 high level
engineering center”, Jiangxi Science
&Technology Normal University, Grant/
Award Number: KFGJ19004
KEYWORDS
diarylethene, fluorescence, magnesium detection, quinoxaline
1 | INTRODUCTION
magnesium is about 300 mg, which could come from sea-
food, vegetables, grains, and dairy products. In the natu-
Magnesium ion, as a rich divalent metal ion in the biol-
ogy and the environment, plays a momentous role in
the cells and environment. In the cellular processes, mag-
nesium is of the essence for biological activities and phys-
iological processes,[1–3] including the regulation of a
hundred of enzymes, structural stabilization of protein,
skeletal development, signal transduction, and the activ-
ity of enzymes involved in ATP synthesis in mitochon-
dria.[4–6] Deficiency of magnesium can result in a
variety of diseases such as hypertension, diabetes,
hypocalcaemia, osteoporosis, and myocardial infarction.
In contrast, the high level of magnesium would lead to
serious age‐related and mental illnesses, however, ratio-
nal amounts of magnesium are advantageous to human
health. As reported, magnesium is a fateful modulator
of cell function, and the overall concentration of magne-
sium ion in mammalian cells should be between 14 and
20 nM [7]; if not, the deficiency of magnesium will lead
to cell death.[8] For an adult, the daily intake of
ral environment, excess magnesium is toxic to plants.
When nutrients are absorbed, antagonistic effects
between ions in crops can be enhanced, however, the
deficiency of magnesium may influence plant develop-
ment and growth,[9–11] leading to the decline in agricul-
tural productivity and quality. Hence, it is valuable to
synthetize a simple, rapid, and sensitive probe of magne-
sium for its distribution and its concentration in the envi-
ronment and cells.[12,13]
As we all know, technologies for detecting biological
and environmental species were reported, for example,
flame atomic absorption spectrometry, spectrophotome-
try, voltammetry, and electrochemical stripping analy-
sis.[14–16] On account of their complicate procedures,
long response and inferior sensitivity was neglected by
people.[17,18] In the last few years, fluorescent probes have
become a valuable detection method for anion, cation,
and biological species because of their high sensitivity,
specificity,
fast
reaction
speed,
and
simple
J Phys Org Chem. 2019;e4030.
wileyonlinelibrary.com/journal/poc
© 2019 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/poc.4030

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ZHANG ET AL.
technology.[19–21] The fluorescent probes are widely used
because it does not need expensive equipment. However,
among the fluorescent probes, diarylethene derivatives
have drawn the attention of many researchers owing to
their advantages—fatigue resistance, thermal stability,
and fast response.[22–25] Furthermore, diarylethene deriv-
atives are the most potential photochromic materials that
can be used as optical memory for optical switching
devices.[26,27] By exposure to light, they can change
between two isomers (the ring‐open and ring‐closed) with
different photophysical properties.[28,29] So, combining
diarylethene with different functional groups to detect
ions is very valuable in the field of fluorescent sensor.
So far, fluorescent probes based on different
fluorophores, including coumarin, rhodamine, pyrrol-
idine, naphthalimides, and calixarene, have been
reported[30–32]; some of them can be used to detect ions
real‐time, including species in cells.[33–35] Meanwhile, a
great number of diarylethene chemosensors that were
based on diarylethene and fluorophore have also been
reported; they can identify various ions, but they have a
shortcoming—most of them cannot identify ions in the
cells. Thus, it is still a challenge to synthesize a probe of
diarylethenes, which can be used to detect species in
cells.[36–40] In summary, fluorescent probes that have
been reported can be used to detect various ions success-
fully. But, most of them mainly recognize copper, mer-
cury, iron, zinc, cyanido, et al. As we all know, among
the reported fluorescent sensor, the fluorescent probe
for Mg2+ based on a diarylethene is rare. Therefore, the
fluorescent probe for magnesium ion detection based on
diarylethene has great potential.
the fluorescent spectrum of the sensor under chemical
species and light stimulation in the methanol solution,
we found that it could be used to recognize Mg2+ with
high selectivity. In addition, the construction of com-
1
pound 1O was characterized by using the H NMR, 13C
NMR, and electrospray ionization mass spectrometry
(ESI‐MS). The photophysical and photochemical behav-
iors of the target compound (1O) were organically stud-
ied. The diagrammatic drawing of photochromism is
shown in Scheme 1.
2 | EXPERIMENTAL
2.1 | General methods
The solvent used in the experiment is pure analytical
after distillation and purification before use. Other
reagents were bought by Dinnochem and used without
1
further purication. H NMR and 13C NMR spectra were
tested on a Bruker AV400 (400 MHz) spectrometer, and
using DMSO as solvent, the internal standard is
tetramethylsilane. The melting point was obtained by
using the WRS‐1B melting point apparatus. A Bruker
amazon SL Ion Trap Mass spectrometer was used to test
the mass spectra. Agilent 8453 UV/Vis spectrophotometer
is used for the measurement of the absorption spectra,
and the equipment of photoirradiation is an MUL‐165
UV lamp and an MVL‐210 visible lamp. Hitachi F‐4600
spectrophotometer was used to get the fluorescence
spectra. PE CHN 2400 analyzer was used to get the ele-
mental analysis. Metal nitrates (Zn2+, Co2+, Al3+, Cd2+
Ni2+, Ba2+, Fe3+, Sn2+, Pb2+, Ca2+, Cr3+, Sr2+, Mg2+
,
,
and Cu2+) and metal chlorides (Ba2+, K+, Hg2+, and
Quinoxaline and its derivatives are important
benzopyrazine compounds with aromatic properties.
Many functional quinoxaline derivatives are expected to
be used as molecular probes, chemical switches and
supramolecular receptors [41–43], and have practical appli-
cations in medical drugs, agricultural drugs, dyes, and
other fields.[44–46] Therefore, the synthesis and research
of quinoxaline compounds have attracted much atten-
tion. Wherefore, a novel fluorescence chemosensor based
on diarylethene‐containing aldehyde group and
quinoxoline group was synthesized (1O) by investigating
Mn2+) are dissolved in deionized water (0.1 mol L−1
)
and used for detection. According to the demands of each
experimental set up, the solution would be diluted.
2.2 | Synthesis of 1O
The route of synthetic of [1‐(2‐methyl‐5‐phenyl‐3‐
thienyl)‐2‐{2‐methyl‐5‐[3‐oxo‐3, 4‐dihydroquinoxaline‐2‐
carbohydrazide] phenyl‐3‐thienyl} perfluorocyclopen‐
tene] (1O) was shown in Scheme 2. In line with the
SCHEME 1 Photochromism of diarylethene 1O

ZHANG ET AL.
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SCHEME 2 Synthetic route of diarylethene 1O
previous methods, compound 5 and 6 were easily synthe-
161.92.Fig. S4. Anal. calcd. for C9H8N4O2 (%): C, 52.94;
H, 3.95; N, 27.44; O, 15.67, found: C, 52.92; H, 3.96; N,
27.44; O, 15.69.
sized in high yield.[38,47]
2.2.1 | Synthesis of quinoxolinone‐2‐ethyl
carboxylate (4)
2.2.3 | Synthesis of [1‐(2‐methyl‐5‐phenyl‐
3‐thienyl)‐2‐{2‐methyl‐5‐[Quinoxolinone‐2‐
hydrazide] phenyl‐3‐thienyl}
In a stirred solution of ethanol of compound 2 (1.08 g, 10
mmol), compound 3 (2.09 g, 12 mmol) of 1.2 equivalent
was added and continuously stirred and refluxed for 6
hours. It was cooled to room temperature, white solid
precipitated, and filtered to get the white solid of com-
pound 4 (2.10 g, 9.63 mmol) with 96% yield. M.p. 425 −
perfluorocyclopentene] (1O)
In a round‐bottom flask, compound 6 (0.274 g, 0.5 mmol)
and 5 (0.102 g, 0.5 mmol) were dissolved with ethanol (10
mL). After being refluxed for 4 hours until reaction
completely, the mixture was cooled to room temperature
and was filtered to get compound 1O (0.261 g, 0.355
mmol), a blue‐green solid in 71% yield. M.p. 559 − 560
K; 1H NMR (400 MHz, DMSO‐d6), δ (ppm): 1.94 (d,
3H), 1.99 (s, 3H), 7.41 (t, 5H), 7.47 (s, 1H), 7.52 (s, 1H),
7.61 (d, 2H), 7.64 (d, 2H), 7.76 (d, 1H), 7.83 (d, 2H), 8.05
(s, 1H), 8.34 (s, 1H), 12.29 (s, 1H), 12.46 (s, 1H) Fig. S5.;
13C NMR (100 MHz, DMSO‐d6), δ (ppm): 14.54, 116.53,
123.02, 123.80, 123.93, 124.23, 124.44, 125.78, 126.07,
127.85, 128.65, 129.33, 129.71, 129.83, 131.65, 132.68,
132.99, 133.70, 134.08, 134.27, 134.64, 141.36, 141.77,
142.21, 144.54, 148.63, 150.97, 153.10, 154.60, 156.36,
160.04, 167.03 Fig. S6.; MS (m/z): 733.1 [M − H+]−; Anal.
calcd. for C37H24F6N4O2S2 (%): C, 60.48; H, 3.29; N, 7.63,
found: C, 60.45; H, 3.24; N, 7.60.
1
426 K; H NMR (400 MHz, DMSO‐d6), δ (ppm): 1.32 (t,
3H), 4.35‐4.38 (m, 2H), 7.37 (t, 2H), 7.65 (d, 1H,), 7.84
(d, 1H), 12.91 (s, 1H)(Fig. S1.); 13C NMR (100 MHz,
DMSO‐d6), δ (ppm): 14.42, 62.19, 116.28, 124.32, 129.61,
131.15, 132.60, 133.17, 150.99, 152.80, 164.13.Fig. S2.
Anal. calcd. for C11H10N2O3 (%): C, 60.55; H, 4.62; N,
12.84: O, 22.00, found: C, 60.53; H, 4.63; N, 12.83; O,
22.02.
2.2.2 | Synthesis of
quinoxolinone‐2‐hydrazide (5)
To a stirred solution of compound 4 (1.09 g, 5 mmol) in
refluxing ethanol, hydrazine hydrate (0.76 g, 15 mmol)
was added, keep stirring for 4 hours. When the reaction
is complete and it is cooled to room temperature, there
is yellow solid separation, concentrated under vacuum,
and the crude product is recrystallized in ethanol with a
3 | RESULTS AND DISCUSSION
1
yield of 78%. M.p. 442 − 443 K; H NMR (400 MHz,
3.1 | Photochromism and fluorescence
DMSO‐d6), δ (ppm): 4.67 (s, 2H), 7.35‐7.39 (m, 2H), 7.61
(d, 1H), 7.83 (d, 1H), 10.04 (s, 1H), 12.85 (s, 1H) Fig.
S3.; 13C NMR (100 MHz, DMSO‐d6), δ (ppm): 115.61,
123.88, 129.24, 131.27, 131.78, 132.31, 150.87, 153.83,
properties of 1O
The fluorescence switching properties and photochromic
properties of compound 1O in methanol solvent was

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ZHANG ET AL.
researched. As shown in the Figure 1A, at room temper-
ature, by alternately irradiating ultraviolet light and visi-
ble light, the ultraviolet (UV) absorption spectrum and
the color of the solution in the methanol solvent changed
significantly in 1O. In the initial state, 1O is in an open‐
loop state, and at 298 nm, a strong ultraviolet absorption
peak appears (mainly caused by the π → π* transition in
the molecule).[48] After irradiation with ultraviolet light
having a wavelength of 297 nm, the absorption peak
was gradually decreased, and the color of 1O changes
from colorless to blue. Meanwhile, a new UV absorption
peak appeared at 601 nm, and the absorbance increased
until the highest value was reached. This indicates that
the ring‐opening state 1O undergoes a closed‐loop reac-
tion and is converted into a closed‐loop state 1C. When
exposed to visible light, 1C undergoes ring‐opening reac-
tion to form 1O, and ultraviolet absorption peak at 601
nm decreases, while the ultraviolet absorption peak
increased at 298 nm. With the irradiation of visible light
(λ > 500 nm), ultraviolet absorption peak returns to the
initial state, and the solution also turns blue into color-
less. When the steady state of the light is reached, it can
be seen from the figure that the equal absorption point
of the substance is at 360 nm.[49]
Figure 1B shows the change in fluorescence emission
intensity of cyclization of compound 1O in the methanol
FIGURE 1 Changes in the absorption spectra of 1O upon alternating irradiation with UV (λ = 297 nm) and visible light (λ > 500 nm) in
methanol (2.0 × 10−5 mol L−1), (A) absorption spectral change and (B) fluorescence change, excited at 380 nm
FIGURE 2 Changes in the fluorescence of 1O induced by the addition of various metal ions (8.0 equivalent) in methanol (2.0 × 10−5 mol
L
−1): (A) emission spectral changes, (B) emission intensity changes. (C) Photos of fluorescence changes in fluorescence

ZHANG ET AL.
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solvent with UV and visible light (λ > 500 nm) irradia-
tion. When excited at 380 nm in methanol, fluorescence
emission peak of the substance at 524 nm exhibits a weak
green fluorescence. Then, irradiated with ultraviolet light,
fluorescence emission intensity of the solution of 1O
gradually decreasesd, and the green fluorescence also
slowly disappeard. This indicates that the cyclization
reaction of 1O produced 1C. When the steady state of
light is reached, the emission intensity is basically
unchanged, and the fluorescence modulation efficiency
of 1O is 90%. However, to irradiate the solution with vis-
ible light, the fluorescence intensity of compound 1O will
gradually increase, and eventually it will reach the initial
height and the fluorescent color will also return to the
initial state. This shows that the cyclization reaction of
1O is a reversible process.
3.2 | Fluorescence response to metal ions
As shown in Figure 2, it is the fluorescence response of
1O to all kinds of ions in methanol solvent. At room tem-
perature, 5.0 times equivalents of all ions were respec-
tively added to the methanol solution of 1O (including
Pb2+, K+, Ni2+, Ca2+, Cd2+, Hg2+, Sr2+, Mn2+, Zn2+
,
Cu2+, Mg2+, Ba2+, Co2+, Sn2+, Cr3+, Al3+, Fe3+). Only
when Mg2+ was added, the fluorescence emission
intensity of the 1O solution increased remarkably, and
emission peak was shifted from 524 nm to 518 nm. The
fluorescence intensity of Zn2+ and Ca2+ slightly
increased, while the other ions did not change (Figure 2
A). The fluorescence intensity of Mg2+ increased by 6.8
times compared with 1O and other ions (Figure 2B).
The fluorescence colors of the solution were also changed
FIGURE 3 Changes in fluorescence of 1O in methanol (2.0 × 10−5 mol L−1) induced by Mg2+/EDTA and light stimuli at room
temperature, excited at 380 nm: (A) 1O induced by Mg2+/EDTA; (fig. Mg2+ fluorescence titration curve of 1O) (B) 1C induced by Mg2+
/
EDTA; (fig. Mg2+ fluorescence titration curve of 1C) (C) 1O′ induced by UV/Vis light; (D) Changes in fluorescence color of 1O, 1O′ , 1C and
1C′ induced by Mg2+/EDTA and light stimuli in methanol (2.0 × 10−5 mol L−1). (E) Changes in absorption spectra and color of 1O and 1O′
induced by UV/Vis lights stimuli in methanol (2.0 × 10−5 mol L−1
)

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ZHANG ET AL.
significantly, which was from the original weak fluores-
cence to a very strong green fluorescence, indicating the
formation of a 1O − Mg2+ complex (Figure 2C). There-
fore, 1O could be used for a fluorescent probe with high
selectivity recognition.
equivalents, the fluorescence intensity reached its maxi-
mum. When a certain amount of EDTA solution is added
to the solution, the fluorescence intensity returns to the
original state of 1C, which indicates that the coordination
of 1C and Mg2+ is also a reversible process. As shown in
Figure 3C, irradiating with ultraviolet light, fluorescence
intensity of compound 1O′ significantly decreased, bright
green fluorescence gradually turn into dim, formed a 1C′,
and the fluorescence emission intensity of compound 1C′
is quenched to 92% compared with 1O′. After visible light
irradiation, 1C' can open ring to generate 1O′, and the
fluorescence color returns to 1O′ state, so the photochro-
mic reaction of 1O′ is also a reversible process. As shown
in Figure 3D, 1O was subjected to changes in fluores-
Figure 3 is mainly to study the fluorescence changes of
1O under the stimulation of Mg2+/EDTA and UV/Vis.
Firstly, Mg2+ fluorescence titration was carried out. As
shown in Figure 3A, the maximum fluorescence intensity
of the compound 1O solution piecemeal increased as Mg2
+
was added dropwise from 0 equivalents to 8.0 equiva-
lents, those may be because the enhancement of chela-
tion fluorescence (CHEF), and inhibits the phototransfer
process, which in turn enhances the fluorescence inten-
sity.[50–52] When Mg2+ was added to 8.0 equivalents, fluo-
rescence emission intensity of the compound 1O solution
reached the maximum, and formed the complex 1O′.
When a certain amount of EDTA solution is added, its
fluorescence emission intensity returns to the original
state of 1O. It is shown that the coordination between
compound 1O and Mg2+ is a reversible process.
cence color under the stimulation of UV/Vis and Mg2+
/
EDTA. The above consequences indicate that fluores-
cence change of compound 1O can be availably adjusted
by the affection with UV/Vis and Mg2+/EDTA.
Furthermore, similar to other diarylethene com-
pounds, 1O′ can also undergo photochromic reaction.
As shown in the Figure 3E, at 298 nm, there is a strong
absorption peak in the initial state. Under the exposure
of 297 nm light, the color of the solution has changed,
which was turning blue. At 601 nm, a fresh absorption
In the uniform experimental conditions, we have per-
formed a fluorescence titration experiment of 1C by Mg2+
(Figure 3B). When Mg2+ was added from 0 to 8.0
FIGURE 4 The limit of detection (LOD) and Hildebrand‐Benesi plot for 1O in methanol (2.0 × 10−5 mol L−1): (A) Job's plot showing the
1:1 complex of 1O and Mg2+; (B) Hildebrand‐Benesi plot based on the 1:1 for 1O, the association constant of 1O with Mg2+ was calculated to
be 1.96 × 105 L mol−1; (C) LOD for Mg2+ was 1.21 × 10‐6 mol L−1

ZHANG ET AL.
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peak was appeared. This is because under the irradiation
of ultraviolet light, a ring‐closing reaction occurs in the
open‐loop 1O′, and a closed‐loop state 1C′ is generated.
Conversely, the closed‐loop state 1C′ is irradiated with
suitable visible light (λ > 500 nm), the blue fade and
become colorless, the ultraviolet absorption also returns
to the position of compound 1O′. When reached the
photostationary state, an equal absorption point appears
at 323 nm.
equation, we concluded that the complexation constant
(Ka) of compound 1O for Mg2+ was 1.96 × 105, and exhib-
ited a very well linear relationship (R = 0.999) as shown
in Figure 4B. As shown in Figure 4C, the detection limit
of compound 1O for Mg2+ is 1.21 × 10−6 mol L−1 and
shows a well‐linear relationship (R = 0.997).
To further determine complexation relationship
between compound 1O and Mg2+, we used mass spec-
trometry data to explore it. In the methanol solution of
1O, a main peak appeared at 733.14 m/z, which
corresponded to compound [1O‐H+]−; after 8.0 equiva-
lents of Mg2+ was added. At 880.9 m/z, a characteristic
peak appeared, which was assigned to [1O + Mg2+
So as to determine the complex ratio of compound 1O
with Mg2+, we conducted a test for the complex ratio
(Figure 4). In the complexation ratio test experiment,
we kept the concentration of 1O and Mg2+ under the
same conditions, and the total volumes of the two
remained unchanged (2000 μL), and change the molar
ratio of compound 1O, make it from 0 to 1, measure the
intensity of fluorescence and make the Job plot curve. It
can be seen from the Job plot curve of Figure 4A that
the value of [1O]/([1O] + [Mg2+]) is 0.5, the value reach
maximum, which indicates that compound 1O and Mg2
+2NO3 ‐H+]−. (Figure 5A). In order to explore more
−
on the coordination of compound 1O with Mg2+, we per-
1
formed the H NMR titration experiments in DMSO‐d6
solvent. As Figure 5B shows, following the addition of
Mg2+, the signal of Ha down shifted from 12.435 to
12.366, and there is a crack peak; The shift of Hc was
shifted from 8.343 to 8.372, and the signal strength
becomes weak, manifesting the coordinated bond of
─CH═N─Mg2+ was formed. And the Hb was shifted
+
are 1:1 bound. For the above 1O fluorescence titration
experiment of Mg2+, in line with the Benesi‐Hildebrand
FIGURE 5 (A) Mass spectra showing
the 1:1 complex of 1O and Mg2+: the mass
1
spectra of 1O and 1O′; (B) H NMR
spectra (400 MHz) measured during the
titration of 1O with Mg2+ in DMSO‐d6

8 of 10
ZHANG ET AL.
from 12.271 to 12.247, it may be affected by the chelation,
thus, exhibited the formation of the coordinate bond of
1O − Mg2+, so, its proposed sensing mechanism of Mg2
values of 0 or 1. For instance, if signal inputs 1 and 3 were
off, and another two inputs were on, that is, In1 = 0, In2
= 1, In3 = 0, In4 = 1, thus, output = 0, indicates that
output signal is off. Similarly, there are many possibilities
for input and output signals of logic gates. Table 1 lists
whole possible logic strings, and the truth table of
homologous output signals. Figure 6B shows the logical
circuit diagram.
+
by 1O was shown in Figure 5B.
3.3 | Application in logic circuit
From all the test results, the fluorescence intensity of
compound 1O can be efficaciously controlled with
UV/Vis, Mg2+/EDTA in methanol, and it can be used in
the design of logic gate circuit. The photoswitching
behaviour of compound 1O was revealed in Figure 6A.
So, on account of the properties of 1O, we integrate four
input signals and one output signal to build a logic gate
(Figure 6). The four inputs are In1: 297 nm UV light,
In2: λ > 500 nm visible light, In3: Mg2+, In4: EDTA.
The output has a fluorescence intensity of 518 nm. For
this logic circuit, the signals of input and the output could
be “off” or “on,” and has a homologous disparate Boolean
3.4 | Application to real samples
In order to explore whether the probe is suitable for sam-
ples, we used water samples of the Ganjiang River of
Nanchang City and the natural water to carry out the
recovery test on the basis of the former methods.[53,54]
First, using the 0.2‐mm membrane to filter the collected
water sample, and diverse amounts of Mg2+ were added,
its test results can be known by a series of calculations. As
shown in Tables 2 and 3, the recovery of Ganjiang River
FIGURE 6 (A) Proposed mechanism of the absorption and fluorescence changes for 1O in the presence of Mg2+ by photo‐irradiation; (B)
combinational logic circuits equivalent to the truth table given in Table 1: In1 (UV light), In2 (visible light), In3 (Mg2+), In4 (EDTA)

ZHANG ET AL.
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for Mg2+ was between 100% and 103%, and in natural
4 | CONCLUSION
TABLE 1 Truth table for all possible strings of four binary‐inputs
data and the corresponding output digit of photochromic behavior
of 1O
A new fluorescent probe has been synthesized, which can
be recognize magnesium ions by fluorescence enhance-
ment. At 524 nm, in the presence of magnesium ions,
its fluorescence intensity enhanced 6.8 times than 1O.
Through ESI‐MS spectra, fluorescence titration experi-
ment, and Job's plot, it was concluded that 1O complexed
with Mg2+ in 1:1. Hence, 1O could be used to detect Mg2+
in a way that fluorescence enhancement. Also, we can
use compound 1O to design logic gates. Furthermore,
the novel probe 1O based on the diarylethenes can be
successful used to detect the Mg2+ in actual water
samples.
Input
Outputa
In4
In1 (UV) In2 (Vis) In3 (Mg2+) (EDTA)
λem = 518 nm
0
0
0
0
0
1
1
1
1
1
1
1
1
0
0
0
0
0
0
1
1
0
1
1
0
0
0
1
1
1
0
1
0
0
1
1
1
0
0
1
1
0
1
1
0
0
1
0
0
1
0
0
1
0
0
0
0
1
1
1
1
1
1
0
0
0
1
1
0
0
0
1
0
0
0
0
0
0
0
0
ACKNOWLEDGEMENTS
The authors are grateful for financial support from
the National Natural Science Foundation of China
(21861017, 41867052, 41867053), the “5511” Science and
Technology Innovation Talent Project of Jiangxi, and
the Open Project Program of “311 high level engineering
center”, Jiangxi Science &Technology Normal University
(No.KFGJ19004) .
ORCID
aWhen the emission intensity at 518 nm more than six fold of the original
state, the output signal is defined as 1, otherwise defined as 0.
Hui Li https://orcid.org/0000-0003-3042-195X
REFERENCES
water, the recovery for Mg2+ was between 98% and
101%. Therefore, 1O can be used to test Mg2+ in the water
samples.
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TABLE 2 Detection of Mg2+ in Ganjiang River samples
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SUPPORTING INFORMATION
Additional supporting information may be found online
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How to cite this article: Zhang Y, Li H, Jiang D,
Pu S. A highly selective fluorescent chemosensor
for Mg2+ based on a diarylethene with a
quinoxaline unit. J Phys Org Chem. 2019;e4030.
https://doi.org/10.1002/poc.4030
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