Fluorescence staining of salicylaldehyde azine, and applications in the determination of potassium tert-butoxide

Article abstract of DOI:10.1039/C6RA01035K

Salicylaldehyde azine (1), with an aggregation-induced emission (AIE) function, was synthesized from salicylaldehyde and characterized by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS), and X-ray single crystal diffraction. Compound 1 exhibited high thermal stability and good light-emitting behavior in the solid state. It could be preferably used to dye cellulose and KBr. No obvious changes in fluorescence intensity occurred when compound 1 was dissolved in different pH buffer solutions. The addition of TFA led to slight fluorescence quenching, and the fluorescence intensity gradually increased with increasing potassium tert-butoxide solution concentrations. The fluorescence intensity of compound 1 showed a good linear relationship with the concentration of potassium tert-butoxide (0.5–4.0 10⁴ M), y ? 99.193x + 93.599, R² ? 0.9902; the limit of detection (LOD) was 1.07 10⁷ M. It could measure the content of potassium tert-butoxide with a relative standard deviation (RSD) value of 1.5%.

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PAPER
Fluorescence staining of salicylaldehyde azine and applications
in the determination of potassium tert-butoxide
a
a
ab
c
a
ab
a
a
Received 00th January 20xx,
Accepted 00th January 20xx
Jinlai Yang, Jian Rui, Xu Xu, Yiqin Yang, Jun Su, Haijun Xu, Yunyun Wang, Nan Sun,
ab
Shifa Wang*
DOI: 10.1039/x0xx00000x
Salicylaldehyde azine (1) with an aggregationꢀinduced emission (AIE) function was synthesized from salicylaldehyde and
characterized by Fourier transform infrared spectroscopy (FTꢀIR), nuclear magnetic resonance (NMR), high resolution mass
spectrometry (HRMS), and Xꢀray single crystal diffraction. Compound 1 exhibited high thermal stability and good lightꢀ
emitting behavior in the solid state. It could be preferably used to dye cellulose and KBr. No obvious changes in
fluorescence intensity occurred when compound 1 was dissolved in different pH buffer solutions. The addition of TFA led
to slight fluorescence quenching, and the fluorescence intensity gradually increased with increasing potassium tertꢀbutoxide
solution concentrations. The fluorescence intensity of compound 1 showed a good linear relationship with the concentration
www.rsc.org/
ꢀ4
2
ꢀ7
of potassium tertꢀbutoxide (0.5ꢀ4.0×10 M), y=99.193x+93.599, R =0.9902; the limit of detection (LOD) was 1.07×10 M.
It could measure the content of potassium tertꢀbutoxide with a relative standard deviation (RSD) value of 1.5%.
Antiꢀcounterfeiting technologies in paper products (banknote) are
3
2,33
1
. Introduction
very important.
Fluorescent materials can identify the source
1
ꢀ9
information after being irradiated, and fluorescence plays a very
important role in the field of antiꢀcounterfeiting.
In recent years, new organic fluorescent probes and solid lightꢀ
3
4ꢀ36
10ꢀ16
Because of good
emitting materials
have been greatly described due to their good
lightꢀemitting behavior, favorable permeability and adhesive force
with cellulose, compound 1 could be used an antiꢀcounterfeiting
material and dye.
Potassium tertꢀbutoxide is an important catalyst and can also be
employed in organic synthesis for condensation, rearrangement,
utility in fluorescence. Many fluorescent compounds with
a
fluorescence enhancement function in a solution state exhibit
fluorescence quenching in the solid state. This has limited the
17
development of fluorescence dyes. Some fluorescent compounds
have been successfully synthesized to overcome this disadvantage
3
7ꢀ40
1
8,19
ringꢀopening, etc.
However, the main method to detect the
such as polythiophene and its derivataives,
as well as
41
2
0
content of potassium tertꢀbutoxide is titration. Thus, it would be
useful to detect the content of potassium tertꢀbutoxide. In this paper,
compound 1 was used to fluorescently detect potassium tertꢀ
butoxide.
tetraphenylethene
derivataives,
1ꢀmethylꢀ1,2,3,4,5ꢀ
21
22
pentaphenylsilole, and pꢀsexiphenyl.
Concurrently, some studies on salicylaldehyde azines have been
2
3,24
reported including pharmacological proprieties
and optical
25,26
properties.
The AIE characteristic of salicylaldehyde azine was
first fully studied by Tang. In addition, twoꢀphoton absorption and
twoꢀphoton excitation fluorescence of salicylaldehyde azines were
2
7
2. Experimental
2
8
2
.1. Materials and instruments
investigated. This was also used as a simple fluorescent probe for
29
Zn(II). Next, some derivatives of salicylaldehyde azine were
synthesized for optical application. A novel fluorescence turnꢀon
detection method in human serum albumin (HSA) and bovine serum
albumin (BSA) in aqueous solution was investigated with 2,4ꢀ
All the raw materials and solvents were purchased from
1
commercial suppliers and used without further purification. HꢀNMR
13
and CꢀNMR spectra were recorded on a Bruker 500 MHz FTꢀNMR
spectrometer in DMSO with TMS as internal standard, respectively.
Fourierꢀtransform infrared (FTꢀIR) spectra were recorded on a
Nicolet 380 FTꢀIR spectrophotometer. Melting points were
measured using an Xꢀ6 microscopic melting point apparatus. UVꢀvis
absorption spectra were measured on a UVꢀ2450 spectrophotometer
3
0
dihydroxylꢀ3ꢀiodo salicylaldehyde azine.
Meanwhile, chloroꢀ
salicylaldehyde azine and bromoꢀsalicylaldehyde azine exhibited
AIEE properties and iodoꢀsalicylaldehyde azine could be applied as
3
1
a turnꢀon fluorescence probe for egg albumin detection.
(
SHIMADZU) using a quartz cuvette with a 1ꢀcm path length.
Fluorescence emission spectra were determined on a Perkin Elmer
LS 55 fluorescence spectrophotometer, excitation wavelength at 385
nm, scan from 450 nm to 750 nm with a 100 nm/min of scan speed.
Fluorescence microscopic images were photographed with
a
fluorescence microscopic imaging system (BX51 Olympus). Xꢀray
data were collected on a Bruker D8 Venture area diffractometer.
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Confocal fluorescence microscopic images were read on a LSM710
confocal laser scanning microscopy.
2
.2. Synthesis of compound 1
A 250 mL dried threeꢀnecked flask equipped with a thermometer,
stirrer and condenser was charged with salicylaldehyde (2.44 g, 20
mmol), and hydrazine hydrate (0.63 g, 10 mmol) in 100 mL of
ethanol. Then the resulting mixture was refluxed for 2 h with a large
amount of precipitation appeared (Scheme 1). The precipitation
was also refluxed with 1 ml hydrochloric acid for 1 h in 100 mL of
ethanol to offer the reaction products, which was purified twice by
recrystallization with 100 mL ethanol. Acicular yellow crystal; yield
Scheme 1. Synthesis of compound 1
3
3
o
ꢀ1
of 90%; mp: 227.2ꢀ227.4 C; FTꢀIR (KBr) ν (cm ): 3436, 1623,
1
1
4
2
1
575, 1486, 1402, 752; H NMR (DMSO, 300 MHz): 6.89ꢀ6.94 (t,
H), 7.32ꢀ7.37 (m, 2H), 7.63ꢀ7.65 (d, 2H), 8.95 (s, 2H), 11.07 (s,
1
3
6
H); C NMR (DMSOꢀd , 75 MHz), δ (ppm): 116.48, 118.15,
Fig. 1 XꢀRay crystal structure of compound 1.
+
19.54, 130.82, 133.16, 158.61, 162.75; HRMS (m/z): [M+H] calcd
for C14H N O +H , 241.0971; found, 241.0959.
12 2 2
+
3
.3. Solid state fluorescence properties
3
. Results and discussion
3.3.1. Fluorescence enhancement properties
3
.1. Synthesis
Stable lightꢀemitting behavior in the solid state is the foundation
of fluorescence. Figs. 2a and 2b show that compound 1 has good
fluorescence and emits Kelly light. To study pH effects, three KBr
pellets were prepared for fluorescence analysis after evenly grinding
Compound
1
was first synthesized by
a
reaction of
salicylaldehyde and aqueous hydrazine. The compound was
1
13
characterized by HRMS, IR, HꢀNMR, CꢀNMR, and Xꢀray single
crystal diffraction (Table S1, Supplementary data and Fig. 1). These
analyses confirmed compound 1 to be a salicylaldehyde azine.
ꢀ6
three different mixtures (a mixture of 1.0 g KBr and 1.0×10 mol
ꢀ6
compound 1; a mixture of 1.0 g KBr, 1.0×10 mol compound 1 and
ꢀ
6
ꢀ6
1
1
.0×10 mol TFA; a mixture of 1.0 g KBr, 1.0×10 mol compound
3
.2. Thermal stability
ꢀ6
and 1.0×10 mol potassium tertꢀbutoxide). The addition of TFA or
Good thermal stability is required for fluorescence dyes, and we
potassium tertꢀbutoxide enhanced the fluorescence (Fig. 2b). TFA
had the most pronounced effects. Thus, the addition of an organic
acid or alkali could not lead to fluorescence quenching in the solid
state.
assessed this for compound 1 using TGA under a nitrogen stream
Fig. S1, Supplementary data). Compound 1 was thermally stable up
(
o
to ca. 232 C corresponding to a 5% of the material weight loss.
Thus, compound 1 had good thermal stability.
3
.3.2. Application of compound 1
Fig. 2 (a) Fluorescence microscopic images (upper) and microscopic images (lower) of compound 1. (b) The fluorescence intensity
of compound 1 as a KBr pellet was affected by TFA and potassium tertꢀbutoxide (λex385 nm). Inset is a photo of compound 1 under a
365 nm light.
2
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ꢀ3
Compound 1 solution (1.0×10 M) was used to dye filter paper,
pledget, cotton and KBr. The images were obtained under sunlight
and 365 nm UV light (Fig. 3). Under sunlight, the color of the dyed
materials changed only a little, but they emitted strong Kelly light
under 365 nm irradiation and could be a fluorescence dye. Confocal
fluorescence microscopy images showed the microstructures of these
dyed materials (Fig. S2). Compound 1 had good permeability with
cellulose and was wellꢀmixed with KBr. Then, an antiꢀcounterfeiting
icon was prepared with compound 1 and filter paper (Fig. S3). The
icon was not seen under the sunlight, but it was very clear under a
Fig. 3 Photographs of filter paper (a), pledget (b), cotton (c)
ꢀ3
dyed by compound 1 (1.0×10 M) and a mixture of compound
ꢀ6
1
and KBr powder (1.0×10 mol/g, d) under sunlight (left) and
3
65 nm irradiation. Compound 1 could also be used to indicate
365 nm UV light (right).
devices at night (Fig. S4).
We next studied the pH effects of compound 1 (1×10 M) with
ꢀ4
water. The light stability test also proved that compound 1 was stable
solutions of buffered 4ꢀ(2ꢀhydroxyethyl)ꢀ1ꢀpiperazineethanesulfonic
on the substrate.
2 5
acid (HEPES, 20 mM, 90% (v/v) C H OH) (Fig. S5). The
3
.4. Optical properties in solution
fluorescence intensity had no significant change in different pH
values; there was no fluorescence quenching. This showed that
compound 1 was stable, and its fluorescence intensity was pHꢀstable.
The adhesive force and influence of light on compound 1 and the
substrate were other important factors influencing the applications.
Thus, a study on adhesive force and influence by light was finished
Compound was readily soluble in methanol, ethanol,
1
isopropanol, ethyl acetate, trichloromethane, dichloromethane, and
cyclohexane. UVꢀvis absorption and fluorescence spectra of
ꢀ4
compound 1 in these solvents (1×10 M) were studied (Fig. S9,
Supplementary data). Compound 1 had two absorption maximum
peaks at 294 nm and 357 nm, and there were no significant changes
in different solvents (Fig. S9a). In contrast, the fluorescence
intensity was markedly affected by solvents (Fig. S9b). A methanol
solution of compound 1 had a peak intensity at 540 nm, but other
solutions redꢀshifted from 540 nm to 550 nm. These solutions of
compound 1 had good fluorescence after dissolution in cyclohexane,
(
Figs. S6, S7, S8). No significant fluorescence quenching occurred
after the dyed pledget and filter paper were washed with water for 5
min and treated with sunlight for 120 h. There was no fluorescence
when they were washed at the same time with ethanol due to the
dye’s solubility in ethanol. The results showed that compound 1 had
good adhesive force because it could not be easily washed off by
ꢀ4
Fig. 4 UVꢀvis absorption spectral change (a) and fluorescence spectral change (b) of compound 1 in ethanol (1.0×10 M) with
ꢀ4
different molar ratios of potassium tertꢀbutoxide and compound 1. The fluorescence intensity of compound 1 in ethanol (1×10 M)
+
with equal K (c) and other metal ions (d), λex385 nm
.
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trichloromethane, dichloromethane, or isopropanol.
To further study the stabilities of compound 1 affected by TFA or
potassium tertꢀbutoxide in solution, the UVꢀvis absorption and
ꢀ4
fluorescence spectra of compound 1 in ethanol (1.0×10 M) with
different equivalents of TFA or potassium tertꢀbutoxide were shown
in Fig. S10 and Fig. 4.
Fig. S10a shows that the absorbance peak was stable with
increasing TFA, but the fluorescence intensity was affected by
increased TFA. This lead to a slight decrease without minimal
changes (Fig. S10b). Compound 1 has two nitrogen atoms and two
42
sites to bind protons. The two nitrogen atoms were unaffected by
+
H , and the UVꢀvis absorption and fluorescence spectra were stable.
Thus, the structure of compound 1 was stable.
Versus Fig. S10a, the absorbance of compound 1 was markedly
affected by potassium tertꢀbutoxide (Fig. 4a). The color turned from
colorless to yellow when the solution of compound 1 had more than
Fig. 5 The linear relationship of peak fluorescence intensity and
the concentration of potassium tertꢀbutoxide.
2
equivalents of potassium tertꢀbutoxide. The absorbance of the two
peaks at 294 nm and 356 nm decreased gradually with the addition
of an increasing potassium tertꢀbutoxide. A new absorption peak
appeared at 411 nm when the molar ratio of potassium tertꢀbutoxide
and compound 1 was 1:1. An obvious absorption peak emerged after
more than 2 equivalents of potassium tertꢀbutoxide were added to
the solution. That is, the color change indicated a response.
The fluorescence spectra of compound 1 in ethanol (1.0×10 M)
with different equivalents of potassium tertꢀbutoxide are also
provided (Fig. 4b). Fluorescence enhancement occurred, and the
for the complex of compound 1 and potassium tertꢀbutoxide (the
stoichiometric ratio was 1:1).
Fig. 5 depicts a good linear relationship of the peak fluorescence
ꢀ
4
intensity and concentration of potassium tertꢀbutoxide (0.5ꢀ4.0×10
2
M), y=99.193x+93.599, R =0.9902. The limit of detection (LOD) for
determining potassium tertꢀbutoxide was 1.07×10 M using 3σbi/m,
where σbi is the standard deviation of six groups of blank signals;
ꢀ4
ꢀ7
4
6
m is the slope of the linear calibration plot. To detect the content of
intensity increased as
a function of potassium tertꢀbutoxide
potassium tertꢀbutoxide purchased from the supplier, two samples of
concentration. The peak fluorescence intensity increased rapidly
with potassium tertꢀbutoxide concentration until 4 equivalents were
added at which point it plateaued.
ꢀ4
compound 1 (1×10 M) with potassium tertꢀbutoxide were prepared
Table S2). The content was calculated after measuring the peak
(
fluorescence intensity of the two samples. The two content were
calculated to be 97.81% and 99.91%. The concentration of
potassium tertꢀbutoxide was successfully measured via this new
method with a RSD of 1.5%. This highlights the utility of compound
+
ꢀ
To study the mechanism, the impact of K and OH was analyzed
(
Fig. 4c). Except potassium tertꢀbutoxide, the addition of
monopotassium phosphate, potassium sulphate, potassium
carbonate, potassium fluoride, or potassium hydroxide, led to no
1
.
ꢀ
significant fluorescence enhancement. Potassium hydroxide had OH
,
which could only lead to a slight fluorescence enhancement. The –
ꢀ
42
OH of compound 1 might lead to deprotonation with OH , but this
was not the main reason for fluorescence enhancement. To further
understand the mechanism, the fluorescence intensity of compound 1
4. Conclusion
Salicylaldehyde azine (1) was directly synthesized from
salicylaldehyde. Compound 1 had good fluorescence, thermal
stability, adhesive forces, and light stability in the solid state. The
dye could be used to dye filter paper, pledget, cotton and KBr. It is a
candidate material for antiꢀcounterfeiting and is a fluorescence
indicator. Compound 1 was stable at different pH values in the
solution state and was not quenched by TFA. However, the
fluorescence intensity of compound 1 gradually increased with
increasing potassium tertꢀbutoxide concentrations. A good linear
relationship of the peak fluorescence intensity and concentration of
ꢀ4
(
1×10 M) and equal metal ion concentrations in ethanol solution
2
+
were discussed (Fig. 4d). The system with Zn
also had
fluorescence enhancement, which agreed with the simple fluorescent
33
probe data. No significant fluorescence change occurred when
other metal ions were added to the solution. The solution with
2
+
compound 1 and Cu had quenching.
2
+
43ꢀ
There are many reasons why Zn might enhance fluorescence.
45
The unfixed C=N structure is nonꢀfluorescent due to the
predominant decay process of C=N isomerization in the excited
states. After complexing with metal ions, the fluorescence increases
strongly because it restricts the rotation of the C=N bond and leads
to the suppression of C=N isomerization. The reason for potassium
ꢀ4
potassium tertꢀbutoxide (0.5ꢀ4.0×10 M) was also obtained
2
ꢀ7
(
y=99.193x+93.599, R =0.9902); the LOD was 1.07×10 M. This is
new tool to measure potassium tertꢀbutoxide concentrations, and it
increases the value of salicylaldehyde azine.
tertꢀbutoxide causing fluorescence enhancement might be
complexation reaction with compound 1, which maintains the Zn
a
2
+
condition. Mass spectrometry (MS) of compound 1 without and with
equivalent of potassium tertꢀbutoxide in ethanol (1×10 M) were
measured by LCꢀMS (Fig. S11). It was clear to see that the m/z
Acknowledgements
ꢀ
4
The authors gratefully acknowledge the project supported by the
Doctorate Fellowship Foundation of Nanjing Forestry University
=
241.3 peak was for compound 1 and another m/z =375.1 peak was
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RSC Advances., 2016, 00, 1-5 | 5

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DOI: 10.1039/C6RA01035K
Graphical Abstract:
Fluorescence staining of salicylaldehyde azine and applications in the
determination of potassium tert-butoxide
a
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ab
c
a
ab
a
Jinlai Yang, Jian Rui, Xu Xu, Yiqin Yang, Jun Su, Haijun Xu, Yunyun Wang, Nan
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ab
Sun, Shifa Wang*