1-[(2-Hydroxy-phenylimino)-methyl]-naphthalen-2-ol: application in detection and adsorption of aluminum ions

Article abstract of DOI:10.1007/s11164-021-04514-7

A novel “on–off” Al³⁺ ions fluorescence-enhanced sensor (E)-1-(((2-hydroxyphenyl) imino)methyl)naphthalen-2-ol (AH-2) and its hydrogel hybrid (PAMN) were synthesized. AH-2 showed excellent selectivity and ultrasensitive to Al³⁺ ions;

Full text of DOI:10.1007/s11164-021-04514-7

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-021-04514-7
1‑[(2‑Hydroxy‑phenylimino)‑methyl]‑naphthalen‑2‑ol:
application in detection and adsorption of aluminum ions
Songsong Xue1 · Zhengfeng Xie1,2 · Jiawei He1
Received: 21 March 2021 / Accepted: 8 June 2021
© The Author(s), under exclusive licence to Springer Nature B.V. 2021
Abstract
A novel “on–of” Al3+ ions fuorescence-enhanced sensor (E)-1-(((2-hydroxyphe-
nyl) imino)methyl)naphthalen-2-ol (AH-2) and its hydrogel hybrid (PAMN) were
synthesized. AH-2 showed excellent selectivity and ultrasensitive to Al3+ ions; the
detection limit was 2.36×10–9 M. The most plausible complexation mechanism was
1
studied by H NMR, FT-IR, HR-MS, Job’s plot and theoretical calculation. And, it
was interesting that PAMN could adsorb Al3+ ions with a removal rate of over 99%,
which also could easily be distinguished by the naked eye in UV lamp (365 nm).
Before and after adsorption of Al3+ ions, the microstructures of PAMN were ana-
lyzed by scanning electron microscope and X-ray energy spectrometer. The silica
gel detect plates prepared in this work could rapidly and conveniently detect Al3+
ions with a concentration greater than 5×10–6 M (0.13 mg/L) in aqueous solution,
and the detection concentration (0.13 mg/L) was lower than the national standard
concentration of Al3+ ions (0.2 mg/L) in city tap water of china.
Keywords Al3+ ions · Fluorescence enhanced · Ultrasensitive · Adsorb · Detection
Introduction
Aluminum (III) is widely used in the felds of mineral material, food additives, clini-
cal drugs, and water treatment [1–4]. It can easily intake the human body through
food and water [5–7]. According to a World Health Organization reported, the mean
daily intake of Al3+ ions is about 3–10 mg/day. If excessive or lacking Al3+ ions, it
may lead to diseases such as encephalopathy, myopathy, and joint diseases [8–15].
* Zhengfeng Xie
xiezhf@swpu.edu.cn
1
Oil and Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College
of Chemistry and Chemical Engineering, Southwest Petroleum University, Sichuan 610500,
China
2
Research Institute of Industrial Hazardous Waste Disposal and Resource Utilization, Southwest
Petroleum University, Sichuan 610500, China
Vol.:(0123456789)
1 3

S. Xue et al.
In China, the national standard for Al3+ ions content in urban tap water is 0.2 mg/L
or less. Thus, it is very important to establish a simple, efcient, and highly sensi-
tive method to detect and remove Al3+ ions in environment and biological system
[16–20].
Compared to some traditional methods of detecting and analyzing Al3+ ions,
sensor detection method and solid-phase extraction method have the advantages of
high sensitivity and convenience. And this method has attracted widespread atten-
tion [21–33]. This paper mainly uses sensor detection method to detect Al3+ ions.
However, various Al3+ ions sensors have been reported [18–24, 34–36]. But as a
hard acid, Al3+ ions tend to coordinate with some hard base coordination atoms
nitrogen and oxygen to form complexes. Schif bases are hard bases that are rich in
nitrogen and oxygen and can be used in coordination with Al3+ ions. Nevertheless,
most has reported Al3+ ions sensors are complex structures and insensitivity to Al3+
ions detection, which greatly limits their applications in the feld of environment and
biology [10–15, 37–43]. So, Schif base fuorescent sensors with simple structure
and sensitivity to Al3+ ions still need a lot of exploration. Moreover, the functions
of these sensors are relatively simple, which can only detect Al3+ ions, but cannot
remove Al3+ ions. In addition, these sensors did not quantitatively detect aluminum
ions. Therefore, it is urgent to design Al3+ ions sensors with simple structure, simple
reaction step, quantitative determination, high sensitivity, and high removal rate.
Hence, based on previous work of our laboratory [26–30, 44–46], a high selectiv-
ity, quantitative determination, simple reaction step, and ultrasensitive Schif base
Al3+ ions sensor (E)-1-(((2-hydroxyphenyl)imino)methyl)naphthalen-2-ol (AH-2)
and its hydrogel hybrid (PAMN) were synthesized. AH-2 exhibited extremely high
selectivity and sensitivity to aluminum ions. And AH-2 can realize the quantitative
detection of aluminum ion. In addition, for better practical applications, the probe
AH-2 was doped into polyacrylamide (PAM) in this experiment to obtain a novel
polymer material (PAMN) that achieves efcient adsorption of aluminum ions.
Experimental
Materials
All chemicals were analytical pure and used without further purifcation. Aniline,
2-aminophenol, 1-naphthaldehyde, and 2-hydroxy-1-naphthaldehyde were pur-
chased from Adamas Reagent Co., Ltd. Acetate, nitrate, potassium, and sodium
salts of cations and anions (K+, Fe3+, Cd2+, Ag+, Zn2+, Co2, Al3+, Hg2+, Cr3+, Cu2+,
Pb2+, Mg2+, Ni2+, Ba2+, Ca2+, Br−, CH3COO−, Cl−, CN−, CO32−, F−, H2PO4−,
−
−
−
HCO3 , HPO42−, HSO3 , I−, NO3 , P2O74−, S2−, PO43−, SCN−) and other reagents
(petroleum, ethyl acetate, ethanol, dimethyl sulfoxide, acetic acid) were purchased
from Chengdu Cologne Chemicals Co., Ltd. In the spectral experiment in this paper,
all cations solutions were prepared from their hydrochloride, acetate, or nitrate con-
fguration. All anion solutions were made from their potassium or sodium salts.
Water was deionized water.
1 3

1‑[(2‑Hydroxy‑phenylimino)‑methyl]‑naphthalen‑2‑ol:…
Scheme 1 The synthetic procedure of fuorescence probe AH-1
Scheme 2 The synthetic procedure of fuorescence probe AH-2
Apparatus
BRUKER AV-400 MHz spectrometer was purchased from BRUKER (Beijing)
Technology Co., Ltd., which used to test and obtain 1H NMR and 13C NMR, operat-
1
ing, respectively, at 400 MHz ( for H) and 101 MHz ( for 13C) using TMS as the
internal standard in DMSO-d6 solvent. Metash UV-6000PC UV–Vis spectrometer
and F-320 fuorescence spectrometer were purchased from Shanghai Metash instru-
ments Co., Ltd, to record the absorption spectra and emission spectra. Hitachi Scan-
ning Electron Microscope SU1510 was purchased from Jiangsu Vanke Science and
Education Instrument Co., Ltd., to obtain SEM and EDS spectra (Scheme 1).
Synthesis of compound AH‑1, AH‑2, AH‑3
The synthetic route of the compound AH-2 is shown in Scheme 2. Specifc steps:
2-aminophenol (0.14 g, 1.3 mmol) and 2-hydroxy-1-naphthaldehyde (0.21 g,
1.2 mmol) were added to the round bottom fask, with 25 mL anhydrous ethanol
as solvent, and then dripped acetic acid (2 mL) into the fask. The reaction system
was refuxed at 80 ℃ for 3 h. The reaction system was cooled at room temperature.
It could achieve a large number of yellow solid precipitated. The yellow solid was
washed with ethanol, which dried in a vacuum drying oven for 48 h. Yields: 87.3%.
1H NMR (400 MHz, DMSO-d6) δ 15.73 (d, J=9.6 Hz, 1H), 10.37 (s, 1H), 9.51 (d,
J=9.1 Hz, 1H), 8.39 (d, J=8.4 Hz, 1H), 7.93 (dd, J=8.1, 1.5 Hz, 1H), 7.80 (d,
J=9.4 Hz, 1H), 7.67 (dd, J=7.9, 1.4 Hz, 1H), 7.48 (ddd, J=8.5, 7.0, 1.4 Hz, 1H),
7.26 (ddd, J=7.9, 7.0, 1.0 Hz, 1H), 7.12 (ddd, J=8.6, 7.3, 1.5 Hz, 1H), 7.02 (dd,
J=8.1, 1.4 Hz, 1H), 6.96 (ddd, J=8.5, 7.3, 1.4 Hz, 1H), 6.80 (d, J=9.4 Hz, 1H).13C
NMR (101 MHz, DMSO-d6) δ 178.10, 149.88, 148.92, 138.41, 134.39, 129.46,
129.05, 128.58, 127.22, 126.32, 125.56, 123.50, 120.30, 120.17, 118.04, 116.44,
108.18 (Fig. S10, Fig. S11). HR-MS, calculated for C17H13NO2: 263.0946, found:
264.1025 [M+H] + (Fig. S12). Elemental analysis: calcd. for C17H13NO2: C 74.99,
H 5.21, N 14.69, found: C 75.05, H 5.01, N 14.61 (Scheme 3).
1 3

S. Xue et al.
Scheme 3 The synthetic procedure of fuorescence probe AH-3
In addition, the synthetic routes of the compounds AH-1 and AH-3 are shown in
supporting information (Fig. S3, Fig. S4, Fig. S5, Fig. S6, Fig. S7, Fig. S8).
Preparation of solution
The concentration of AH-1, AH-2, and AH-3 was 1.0×10–3 M with DMSO as sol-
vent. The concentration of cations or anions solution was 1.0×10–1 M with deion-
ized water as solvent. In this experiment, all spectra tests were carried out in the
solution of DMSO/H2O (V:V=1:99, pH=7).
Removal rate experiment
After PAMN-adsorbed Al3+, the removal rate (Q) was calculated by the following
formula:
Ci − Cf
Q =
× 100%
(1)
Ci
Q: ions removal rate, Ci: ions initial concentration, Cf : ions fnal concentration.
Results and discussion
Selective recognition of cations or anions by AH‑2
The response properties of AH-2 to cations and anions (K+, Fe3+, Cd2+,
Ag+, Zn2+, Co2, Al3+, Hg2+, Cr3+, Cu2+, Pb2+, Mg2+, Ni2+, Ba2+, Ca2+, Br−,
−
−
−
CH3COO−, Cl−, CN−, CO32−, F−, H2PO4−, HCO3 , HPO42−, HSO3 , I−, NO3 ,
P2O74−, S2−, PO43−, SCN−) were investigated by means of UV–Vis spectropho-
tometer and fuorescence spectrophotometer. Figure 1a, b is the ultraviolet spec-
trum of AH-2 on cations and anions in the solution of DMSO/H2O (V:V = 1:99,
pH = 7). It showed the addition of cations, the maximum absorption wavelength
of AH-2 almost unchanged, but the maximum absorption peak had a certain dif-
−
ference (Fig. 1a). It also could be seen that when CN−, HPO42−, P2O74−, HCO3 ,
3−
S2−, PO4 ions were added, the maximum absorption wavelength of AH-2 had
a bathochromic shift, and other anions did not have bathochromic shift phenom-
enon (Fig. 1b). Figure 1c, d is the fuorescence spectra of AH-2 on cations and
1 3

1‑[(2‑Hydroxy‑phenylimino)‑methyl]‑naphthalen‑2‑ol:…
Fig. 1 a, b UV–Vis spectra of AH-2 (1.0×10–5 M) in DMSO/H2O (V:V=1:99, pH=7) upon addition
of various ions (1.0×10–4 M); c, d fuorescence spectra of AH-2 (1.0×10–5 M) and upon the addition of
various ions (1.0×10–4 M) in DMSO/H2O (V:V=1:99, pH=7) (λex =461 nm); e, f fuorescence spectra
of AH-2 (1.0×10–5 M) and upon the addition of various ions (1.0×10–4 M) in DMSO/H2O (V:V=1:99,
pH=7, Blank: refers to the AH-2 solution without adding any ions)
anions in the solution of DMSO/H2O (V:V = 1:99, pH = 7). From the fuorescent
emission spectra, it could be seen that only the fuorescence intensity of AH-
2 after adding Al3+ ions had been greatly enhanced at 527 nm, which exhib-
ited obvious fuorescence enhancement phenomenon. The fuorescence intensity
increased from 9.6 to 1343.09, which increased by about 140 times. However,
the fuorescence intensity of AH-2 at 527 nm substantially had little changed
after adding other cations or anions. From Fig. 1e, f, it could be observed that
only the fuorescence intensity of the probe after adding Al3+ ions had a strong
enhancement phenomenon and presented a strong yellow-green fuorescence.
And as shown in Fig. 2a, c, AH-1 and AH-3 did not respond to Al3+ ions under
1 3

S. Xue et al.
Fig. 2 a, b, and c Fluorescence spectra of AH-1, AH-2, AH-3 (1.0×10–5 M) and upon the addition
of Al3+ ions (1.0×10–4 M) in DMSO/H2O (V:V=1:99, pH=7) (λAH-1ex =453 nm, λAH-2ex =461 nm,
λAH-3ex =406 nm)
DMSO/H2O (V:V = 1:99, pH = 7). According to the above phenomenon, it was
also indicated that probe AH-2 had good specifc recognition properties for Al3+
ions.
Competitive experiments of AH‑2 on Al3+
The presence of other ions may interfere with the detection of target ions, so a
competitive experiment was carried out in this experiment. 10 equiv. of other
ions were added to the DMSO/H2O (V:V = 1:99, pH = 7) solution of AH-2, and
then 10 equiv. Al3+ ions were also added. As shown in Fig. 3a, b, the fuores-
cence intensity of AH-2 was substantially unchanged before Al3+ ions were
added. When Al3+ ions were added, the fuorescence intensity of AH-2 had
obvious fuorescence enhancement. Therefore, AH-2 could be used as an Al3+
ions probe, which had an excellent anti-interference ability.
1 3

1‑[(2‑Hydroxy‑phenylimino)‑methyl]‑naphthalen‑2‑ol:…
(a)
probe + metal ions
probe + metal ions + Al3+
1400
1200
1000
800
600
400
200
0
+
2+ 2+
Mg Ni
2+
+
2+
3+
2+
Zn
2+ 2+
3+
2+
Pb
2+
Cr
2+
Blank
Ag
Hg
k
Cu
Fe
Ba Ca
Co
Cd
probe + anions
probe + anions + Al3+
(b)
1400
1200
1000
800
600
400
200
0
-
-
N
-
-
-
-
-
-
-
N
-
O
-
-
-
4-
7
O
k
2
2-
S
3-
n
I
r
F
3
4
3
3
a
3
B
Cl
l
O
O
O
O
C
4
4
O
O
B
PO
C
N
SC
C
HS
PO
2
2
HC
P
3
H
HP
H
C
Fig. 3 a, b Interference experiments with Al3+ (1.0×10–4 M) and ions coexisting in DMSO/H2O
(V:V=1:99, pH=7) (λex =461 nm)
The sensitivity of AH‑2 to Al3+
Sensitivity is one of the important indicators of probe performance. Within a cer-
tain range of Al3+ ions concentration (5.0×10–8 ~1.0×10–5 M), the fuorescence
titration experiment was carried out. Figure 4a shows the gradual change between
the fuorescence intensity of AH-2 and the concentration of Al3+ ions when Al3+
ions of diferent concentrations were added to AH-2. It could be seen that with the
increase of Al3+ ions concentration, the fuorescence intensity of AH-2 increased
gradually, and there was obvious fuorescence enhancement. In addition, the fuo-
rescence intensity enhancement demonstrated a good linear relationship over Al3+
1 3

S. Xue et al.
Fig. 4 a Fluorescence spectra of AH-2 (1.0×10–5 M) in DMSO/H2O (V:V=1:99, pH=7) upon the addi-
tion of Al3+ (5.0×10–8 ~1.0×10–5 M) and b the linear relationship between fuorescence intensity of
AH-2 and the diferent concentrations of Al3+
ions (R2 =0.9942) (Fig. 4b), and the detection limit of AH-2 toward Al3+ was deter-
mined to be as low as 2.22×10–9 M on the basis of 3σ/k, indicating high sensitivity
of probe AH-2 for quantitative determination of Al3+ [31, 44–46]. Therefore, AH-2
showed super sensitivity to Al3+ ions and could be used to detect Al3+ ions.
Mechanism exploration experiments
Explore the optimal detection mechanism of AH-2 and Al3+. Firstly, the Job’s
plot was measured to determine the optimal stoichiometric ratio of the interaction
between AH-2 and Al3+ ions. The results showed that the complexation ratio of
1
AH-2 and Al3+ ions was 1:1 (Fig. S16). Then, H NMR titration experiments were
executed in DMSO-d6 by the gradual addition of Al3+ ions to elucidate the plausible
1
intermolecular interactions between probe AH-2 and Al3+ ions. Figure 5 shows H
NMR spectra of AH-2 in DMSO-d6 solution with the addition of increasing concen-
trations of Al3+ ions. Figure 5c, in AH-2, the naphthol hydroxyl proton locating at
15.73 ppm was characteristic of an intramolecular hydrogen bond (Ha), the proton
peak of phenolic hydroxyl (Hb) was at 10.37 ppm, and the proton peak of –CH=N
was at 9.51 ppm. Figure 5a, b shows the addition of Al3+ ions, the peaks of Ha and
Hb disappeared completely [47, 48]. These results showed that AH-2 coordinates to
Al3+ ions with naphthol hydroxyl, phenolic hydroxyl, and imine groups. And these
experimental results could be verifed by FTIR (Fig. 6). Figure 6 shows that the C=N
stretching vibration peak in AH-2 appears at 1631 cm−1. When AH-2 was complex
with Al3+ ions, its C=N stretching vibration peak shifts to 1637 cm−1, which was
6 cm−1 compared with the displacement of C=N stretching vibration peak in AH-
2. And at 1361 cm−1 was the OH peak on the benzene ring of AH-2. When AH-2
was complex with Al3+, the OH peak shifts to 1377 cm−1, which showed a change
of 16 cm−1. It demonstrated that AH-2 forms a complex with Al3+ ions. The above
experimental results could also be verifed by mass spectrometry (Fig. S13) [AH-
2+Al3+ +2Na+ +CH3OH]+, m/z=366.0686, calcd for: 366.0635). According to the
1 3

1‑[(2‑Hydroxy‑phenylimino)‑methyl]‑naphthalen‑2‑ol:…
Fig. 5. 1H NMR spectra of AH-2 with Al3+ ions in DMSO-d6
Fig. 6 FT-IR of AH-2 and AH-2+Al3+
experimental results and literature [47, 48], the most plausible mechanism of AH-2
and Al3+ ions is shown in Fig. 7.
In addition, in order to further understand the electronic structure of AH-
2 and AH-2-Al3+ and verify the experimental results, density functional theory
1 3

S. Xue et al.
Fig. 7 The optimal detection mechanism of AH-2 toward Al3+
was adopted in this paper. The calculation of complex was done based on the
1
1:1 stoichiometric ratio obtained from Job’s plot, H NMR and HR-MS analy-
sis. The structure of the optimized Al3+ complex indicated the tridentate behav-
ior (O, N, O) of AH-2 toward Al3+ (Fig. S17). In addition, the stability of AH-
2 and AH-2-Al3+ structures was analyzed by calculation. Figure 8 shows that
HOMO–LUMO energy diference was 0.13414 eV for AH-2. After AH-2 inter-
acting with Al3+, the energy diference decreased to 0.07054 eV. The decrease in
HOMO–LUMO energy diference indicated the formation of AH-2-Al3+ complex
structure. And AH-2-Al3+ complex structure was more stable than AH-2. The
above results better verify the possible mechanism of AH-2 recognition of Al3+ is
shown in Fig. 7.
Fig. 8 The optimized structures of AH-2 and AH-2+Al3+ and electron distribution of the HOMO and
LUMO energy levels
1 3

1‑[(2‑Hydroxy‑phenylimino)‑methyl]‑naphthalen‑2‑ol:…
Adsorption experiment
A novel Al3+ adsorption material (PAMN) was prepared by doping AH-2 with
polyacrylamide (PAM). It was hoped that based on the coordination of AH-2
and Al3+, a better removal of Al3+ could be achieved. Before adsorption of Al3+,
PAMN presented a yellow solid under natural light (Fig. 9a). PAMN presented
a no light under UV lamp (Fig. 9b). After adsorption of Al3+, PAMN presented
yellow hydrogels under natural light (Fig. 9(c)). PAMN presented a light yellow
light (Fig. 9d), which formed a sharp contrast with before adsorption. It indicated
that PAMN could be used as a material to remove Al3+ ions. After adsorption by
PAMN, the concentration of Al3+ ions in aqueous solution was determined to be
1.92 × 10–7 M. The experiment result showed that the removal rate of Al3+ was
99% by PAMN. It showed that PAMN was a kind of high efcient material for
removal of Al3 + ions.
And, the microstructure of PAMN before and after adsorption was observed.
Before the adsorption, it could be observed that the surface of PAMN has uneven
folds and pores (Fig. 10a, b) and its surface was free of Al3+ ions (Fig. 10c). Nev-
ertheless, after the adsorption, the surface of PAMN presented a dense similar
rose-petal structure (Fig. 10d, e) and presented Al3+ ions in its surface (Fig. 10f).
The dense similar rose-petal structure could efectively keep the adsorbed Al3+
ions from being lost easily, so as to better absorb Al3+ ions. It is suggested that
PAMN could be used to remove Al3+ ions in the environment felds.
Fig. 9 a and b images of PAMN under natural light and 365 nm under ultraviolet light without Al3+
adsorption, respectively; c, d images of PAMN under natural light and 365 nm under ultraviolet light
with Al3+ adsorbed, respectively
1 3

S. Xue et al.
Fig. 10 (a), (b) SEM images and (c) EDS images before PAMN adsorption of Al3+; (d), (e) SEM images
and (f) EDS images after PAMN adsorption of Al3+
Actual water sample detection experiment
Taking into account the toxicity of Al3+ ions, actual water sample detection
experiment was explored to verify the practicability of the probe AH-2 in the
actual environment. The water samples were picked from lake water, tap water,
and mineral water. The ability of AH-2 to detect Al3+ ions in actual water sam-
ples was evaluated. The recovery experiment was carried out by the standard
addition method, and three concentrations Al3+ (1, 2, 3 μM) were added to dif-
ferent water samples, and the Al3+ ions concentration in the water samples was
determined by fuorescence spectroscopy. As shown in Table 1, the recovery rate
of Al3+ was between 98.0% and 146.0% in the water sample. The results indicated
Table 1. Determination of Al3+ in diferent water samples
Sample
Add (μM)
Found (μM)
Recovery (%)
R.S.D. (n=3) (%)
Lake water
1.00
2.00
3.00
1.00
2.00
3.00
1.00
2.00
3.00
1.46
2.45
3.42
1.13
2.11
3.18
0.98
2.03
3.05
146.0
122.5
114.0
113.0
105.5
106.0
98.0
2.05
1.87
2.23
1.77
2.33
1.95
2.96
2.54
1.92
Tap water
Mineral water
101.5
101.7
1 3

1‑[(2‑Hydroxy‑phenylimino)‑methyl]‑naphthalen‑2‑ol:…
that AH-2 could be used for the quantitative detection of Al3+ ions in actual water
samples with high accuracy and precision.
Detection experiment
In order to rapidly and conveniently detect the concentration of Al3+ ions in aque-
ous solution, silica gel detect plates were prepared, which were used to detect
the Al3+ ions solution with a certain concentration (5 × 10–9 ~ 5 × 10–5 M). Fig-
ure 11a-1, a-2 shows the photographs under natural light and UV lamp when dif-
ferent concentrations of Al3+ ions (1: 5 × 10–9 M; 2: 5 × 10–8 M; 3: 5 × 10–7 M; 4:
5 × 10–6 M; 5: 5 × 10–5 M) were added to the DMSO/H2O (V:V = 1:99, pH = 7)
of AH-2. Figure 11a-1 shows that there was no diference after adding diferent
concentrations of Al3+ to AH-2 under natural light. Figure 11(a-2) shows that the
fuorescence of AH-2 gradually increased under the UV lamp. Figure 11b shows
that Al3+ ions solution (concentration > 5 × 10–6 M) was dropped on silica gel
detection plate, and bright yellow fuorescence could be clearly observed under
UV lamp (365 nm). While when the concentration was less than 5 × 10–6 mol/L,
there was no light. It is indicated that silica gel detect plates could be used for the
rapid and convenient detection of Al3+ ions (concentration > 5 × 10–6 M) in on-
site environment.
Fig. 11 a-1 and a-2 were the photographs under natural light and UV lamp when diferent concentrations
of aluminum ions were added to the DMSO/H2O (V:V=1:99, pH=7) of AH-2; b-1 images of silica gel
detection plates (bottom) and silica gel plates (top) under natural light; b-2 images of silica gel detection
plates (bottom) and silica gel plates (top) under UV lamp (365 nm); b-3 images of silica gel detection
plates (bottom) and silica gel plates (top) under UV lamp (365 nm) after adding diferent concentration
(1: 5×10–9 M; 2: 5×10–8 M; 3: 5×10–7 M; 4: 5×10–6 M; 5: 5×10–5 M) of Al3+ ions
1 3

S. Xue et al.
Conclusion
Summary, a simple probe AH-2 based on 1-[(2-hydroxy-phenylimino)-methyl]-
naphthalen-2-ol Schif base was designed and synthesized, which was capable of
selectively detecting Al3+ ions. Probe AH-2 displayed preeminent selectivity and
superior sensitivity toward Al3+ ions. Moreover, AH-2 could be served as a prac-
tical fuorescent chemosensor for rapid monitoring of Al3+ ions by virtue of silica
gel plates, indicating that AH-2 has potential practical application value. More
importantly, AH-2 was doped into PAM to prepare a novel type of adsorption
material (PAMN) that has a high-efciency adsorption efect on Al3+ ions. We
expect probe AH-2 can extend its potential applications in environment and bio-
logical systems.
Supplementary Information The online version contains supplementary material available at https://doi.
org/10.1007/s11164-021-04514-7.
Acknowledgements The author is grateful to project supported by the Sichuan Youth Science and Tech-
nology Innovation Research Team Project (No.2020JDTD0018).
Declarations
Confict of interest The authors declare that they have no known competing fnancial interests or personal
relationships that could have appeared to infuence the work reported in this paper.
References
1. Y.K. Jang, U.C. Nam, H.L. Kwon, C. Kim, Dyes. Pigm. 99, 6 (2013)
2. N. Behera, V. Manivannan, J. Photoch. Photobio. A. 353, 77 (2018)
3. R. Jalili, A. Khataee, Microchim. Acta. 186, 29 (2018)
4. A.A. Rodrigues, S.C. Vasconcelos-Filho, G.M.L. Rehn, D. Rodrigues, C.L. Rodrigues, C. Muller,
Flora 236, 9 (2017)
5. J.G. Martinez, T.F. Otero, Sens. Actuators. B. 195, 365 (2014)
6. K. Shen, S. Mao, X. Shi, Luminescence 33, 54 (2018)
7. Z. Xie, M. Fu, B. Yin, Q. Zhu, Chin. Chem. Lett. 38, 124 (2018)
8. G. Yang, X. Meng, S. Fang, New. J. Chem. 42, 14630 (2018)
9. N. Chatterjee, S.B. Maity, A. Samadder, Rsc. Adv. 6, 17995 (2016)
10. S. Kim, J.Y. Noh, S.J. Park, Rsc. Adv. 4, 18094 (2014)
11. L.K. Kumawat, N. Mergu, M. Asif, V.K. Gupta, Sens. Actuators. B. 231, 847 (2016)
12. S.K. Mittal, R. Sharma, M. Sharma, A. Mittal, J.P. Sharma, J. Appl. Electro. Chem. 44, 1239 (2014)
13. M. Soylak, S. Saracoglu, L. Elci, M. Dogan, Int. J. Environ. An. Ch. 82, 225 (2010)
14. M. Tuzen, M. Soylak, Anal. Chim. Acta. 504, 325 (2004)
15. T.T. Wei, J. Zhang, G.J. Mao, Anal. Methods. 5, 324 (2013)
16. C. Lim, H. Seo, J.H. Choi, S.H. Kim, S. Song, E.H. Kim, S. Lim, C. Choi, H.H. Ji, J. Photoch. Pho-
tobio. A. 356, 312 (2018)
17. S. Ma, L. Li, M. She, M. Wang, R. Li, Chin. Chem. Lett. 28, 214 (2017)
18. C. Arroyave, J. Barcelo, C. Poschenrieder, R. Tolra, J. Inorg. Biochem. 105, 1477 (2011)
19. X. Qiao, M. Wei, T. Dong, F. Xia, P. Chen, C. Zhou, J. Electroanal. Chem. 808, 35 (2018)
20. C. Sun, X. Miao, L. Zhang, W. Li, Z. Chang, Inorg. Chim. Acta. 478, 112 (2018)
21. X. Wen, Z. Fan, Anal. Chim. Acta. 945, 75 (2016)
22. S. Dey, S. Halder, A. Mukherjee, K. Ghosh, P. Roy, Sens. Actuators. B. 215, 196 (2015)
1 3

1‑[(2‑Hydroxy‑phenylimino)‑methyl]‑naphthalen‑2‑ol:…
23. D.P. Singh, R. Dwivedi, A.K. Singh, B. Koch, P. Singh, V.P. Singh, Sens. Actuators B Chem. 238,
128 (2017)
24. Y. Xu, S. Mao, H. Peng, F. Wang, H. Zhang, S.O. Aderinto, H. Wu, J. Photoch. Photobio. A. 332,
273 (2017)
25. Y.C. Chu, Z.F. Xie, D.J. Zhuang, Y.-Y. Yue, Y.-H. Yue, W. Shi, S. Feng, Chin. J. Chem. 37, 1216
(2019)
26. Y.-B. Chen, W. Shi, Y.-H. Hui, X.-H. Sun, L.-X. Xu, L. Feng, Z.-F. Xie, Talanta 137, 38 (2015)
27. Y.-C. Chu, Z.-F. Xie, Y.-S. Yue, Y.-S. Yue, X.-J. Kong, W. Shi, S. Feng, ACS Omega 24, 5367
(2019)
28. Z.-F. Xie, X.-J. Kong, L. Feng, J.C. Ma, Y.-Q. Li, X. Wang, W.-R. Bao, W. Shi, Y.H. Hui, Sens.
Actuators B Chem. 257, 154 (2018)
29. L. Feng, W. Shi, J.-C. Ma, Y.-B. Chen, F. Kui, Y.-H. Hui, Z.F. Xie, Sens. Actuators B Chem. 237,
563 (2016)
30. D. Chen, J. Yang, J. Dai, X. Lou, X. Fan, J. Mater. Chem. B. 32, 1033 (2018)
31. H. Abdolmohammad-Zadeh, E. Rahimpour, Anal. Chim. Acta. 881, 54 (2015)
32. M.M. El-Wekil, H.R.H. Ali, A.A. Marzouk, R. Ali, New J. Chem. 42, 9828 (2018)
33. B.A. Alyami, A.M. Mahmoud, S.A. Alkahtani, M.M. El, Talanta. 226, 122167 (2021)
34. J.H. Jou, H.H. Yu, Y.X. Lin, J.R. Tseng, S.H. Peng, Y.C. Jou, C.H. Lin, S.M. Shen, C.Y. Hsieh,
M.K. Wei, J. Fluoresc. 27, 1191 (2017)
35. J. Qin, Z. Yang, J. Photoch. Photobio. A. 303, 99 (2015)
36. L. Wang, L. Yang, D. Cao, Sens. Actuators B Chem. 202, 949 (2014)
37. J. Zhang, S. Wang, C. Liu, G. He, T. Peng, Chin. J. Chem. 36, 1179 (2018)
38. K. Deng, L. Wang, Q. Xia, R. Liu, J. Qu, Sensor. Actuat. B-Chem. 296, 126645 (2019)
39. Z. Li, W.-H. Chen, L.-Y. Dong, Y. Song, R.-H. Li, Q. Li, D.-H. Qu, H. Zhang, Q.-B. Yang, Y.-X. Li,
New J. Chem. 44, 3261 (2020)
40. Z. Li, F.-C. Dai, J. Wang, S.-H. Wang, L.-W. Xiao, L.-L. Li, Synthetic Met. 39, 116234 (2020)
41. Y. Wang, Z. Fan, S. Lei, X. Kong, L. Hou, X. Shao, Spectrochim. Acta. A. 208, 131 (2019)
42. P.P. Soufeena, K.K. Aravindakshan, J. Lumin. 205, 400 (2019)
43. Y.-Y. Yue, Z.-F. Xie, Y.-C. Chu, S.-S. Xue, Chin. J. Org. Chem. 40, 501 (2020)
44. X.-D. Ren, Z.-F. Xie, H.-Q. Wu, W. Shi, Y. Zhang, Colloid. Surface. A. 583, 124003 (2019)
45. Y.-P. Hao, Z.-F. Xie, W.-R. Bao, X. Wang, W. Shi, Chin. J. Org. Chem. 38, 2109 (2018)
46. C. Wang, L.-Z. Wang, S.-M. Fang, D.-W. Qin, J.-H. Zhou, G. Yang, S.-S. Jin, H.D. Duan, Res.
Chem. Intermediat. 45, 2045 (2019)
47. A. Ghosh, A. Sengupta, A. Chattopadhyay, D. Das, Rsc. Adv. 5, 24194 (2015)
48. L.-J. Hou, W.-T. Liang, C.-H. Deng, C.F. Zhang, B. Liu, S.-M. Shuang, Y. Wang, Rsc. Adv. 10,
21629 (2015)
Publisher’s Note Springer Nature remains neutral with regard to jurisdictional claims in published
maps and institutional afliations.
1 3