An acid-base resistant Zn-based metal-organic framework as a luminescent sensor for mercury(II)

Article abstract of DOI:10.1016/j.jssc.2019.121153

A monocyclic organic ligand 5-aminoisophthalic acid (H₂APA) with one amino and two carboxylic groups, has been employed to construct a stable Zn-based metal-organic framework, ZnAPA. It features a 3D supramolecular network containing the pores

Full text of DOI:10.1016/j.jssc.2019.121153

Journal of Solid State Chemistry 283 (2020) 121153
Contents lists available at ScienceDirect
Journal of Solid State Chemistry
journal homepage: www.elsevier.com/locate/jssc
An acid-base resistant Zn-based metal-organic framework as a luminescent
sensor for mercury(II)
,
,**
Junling Jiang a, Yantong Lu a, Jingwen Liu a, Yunchun Zhou b, Dian Zhao a *, Chunxia Li a
a Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, Jinhua, 321004, China
b National Analyticla Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022,
PR China
A R T I C L E I N F O
A B S T R A C T
Keywords:
A monocyclic organic ligand 5-aminoisophthalic acid (H2APA) with one amino and two carboxylic groups, has
been employed to construct a stable Zn-based metal-organic framework, ZnAPA. It features a 3D supramolecular
network containing the pores with a size of 8.2 Å and uncoordinated carboxylic oxygen atoms, exhibiting a
pronounced fluorescence response (fast response, high sensitivity and selectivity) to Hg2þ ion over other metal
ions in aqueous solution. The possible fluorescence-based sensing mechanism is also involved. Importantly,
ZnAPA shows extraordinary acid-base resistant stability, highlighting its potential use for detection of Hg2þ in
practical applications.
Metal-organic frameworks
Extraordinary chemical stability
Heavy metal detection
Mercury(II)
Fluorescent probe
1. Introduction
attention [10,11].
Metal-organic frameworks (MOFs), constructed from the metal-
Along with the rapid development of modern industry, the use of
waste water containing industrial and artificial discharges for agriculture
lead to heavy metal accumulation in water and land, which has been a
serious threat to food safety and public health [1,2]. Mercury(II) (Hg2þ),
a typical toxic and dangerous heavy metal ion, which is widely existed in
the air, water and soil due to the slather using in industry and agriculture
[3]. As such metal contaminant is not biodegradable and of high affinity
for thiol group in enzymes and proteins, it tends to accumulate in the
living organisms and leads to the dysfunction of cells and consequently
bringing many health diseases in kidney, brain, central nervous and
endocrine systems [4,5]. Thus, accurate detection of Hg2þ ions is a very
important task to ensure the safe and health of human. At present, many
techniques have been developed for detecting and quantifying Hg2þ ions,
such as atomic absorption spectrum (AAS) [6,7], liquid chromatography
[8], inductively coupled plasma atomic emission spectrum (ICP-AES) [9]
and so on; however, most of them rely on large instruments, and are
time-consuming, expensive and indirect-viewed. Therefore, it is of great
significance to develop simple, fast, visual, highly sensitive and specific
methods for detection of trace aqueous Hg2þ ions. Fluorescence-based
methods, in view of their marked virtues including high selectivity and
sensitivity, visualization, ease of operation, have attracted tremendous
containing nodes or clusters and the organic ligands, have attracted
growing attention in many applications, such as gas storage and sepa-
ration, catalysis, energy conversion, optoelectronics, and solid-state
lighting [12–19]. By combining the tunable optical properties and per-
manent porosity, luminescent MOFs have been regarded as promising
alternatives to develop multifunctional materials for different sensing
applications [20,21]. They can reversibly uptake and release guest spe-
cies, such as molecules and ions, and to offer a platform for specific
luminescent sensing and recognition of targets based on the host-guest
interactions. In this content, considerable efforts have been devoted to
exploit diverse sensory materials based on luminescent MOFs [21–27].
Over the past decade, a number of luminescent MOFs for sensing heavy
metal ions, including Hg2þ, have been realized [28–32]. Despite already
preliminarily investigated, engineering a luminescent MOF with stable
structure and high selectivity and sensitivity for detection of Hg2þ ions in
aqueous solution is still a challenge [33].
To improve the structure stability of luminescent MOF sensors toward
various harsh conditions, especially the strong acidic/basic aqueous so-
lution, great efforts have been made to engineer the topology and
structural composition, pore size and shape, as well as ligand modifica-
tions of MOFs [34–37]. As is well known, most Zn-based MOFs
* Corresponding author.
** Corresponding author.
E-mail addresses: dzhao@zjnu.edu.cn (D. Zhao), cxli@zjnu.edu.cn (C. Li).
https://doi.org/10.1016/j.jssc.2019.121153
Received 12 November 2019; Received in revised form 16 December 2019; Accepted 23 December 2019
Available online 24 December 2019
0022-4596/© 2019 Elsevier Inc. All rights reserved.

J. Jiang et al.
Journal of Solid State Chemistry 283 (2020) 121153
comprising of the traditional paddle-wheel structures are subject to hy-
drolysis when exposed to moisture for a while, showing very poor
chemical durability [38–40]. We thus attempt to develop an acid-based
resistant Zn-based MOF for selectively recognition of the aqueous Hg2þ
ions. In this work, a multi-coordination organic ligand, 5-aminoisoph-
thalic acid (H2APA, Fig. 1a), was selected to construct the target lumi-
nescent Zn-based MOF. Compared with the reported synthetic
procedures [41], we synthesized the MOF crystals under the moderate
conditions. Of note, the monocyclic ligand, possessing three potential
coordination groups and conjugate alkaline center, is an ideal organic
linker for building stable MOFs. In addition to the carboxylate groups, the
amino group can interact strongly to the zinc ions, benefiting to the
construction of a chemical stable framework [40]. Moreover, hydrogen
bonds are frequently present in the framework, which further improve
the thermal stability of the crystal structure. As expected, the
as-synthesized MOF Zn(APA)(H2O) (ZnAPA) features a 3D supramolec-
ular network containing the pores with a size of 8.2 Å and uncoordinated
carboxylic oxygen atoms, showing a linear fluorescence response to the
concentration of Hg2þ ion in aqueous solution. The possible sensing
mechanism is also investigated. Notably, we found that ZnAPA presents
excellent acid-base resistance and thermal stability. These features make
ZnAPA a potential fluorescence probe for the selective detection of Hg2þ
ions in the industrial and artificial waste water.
spectrometer with a dual anode Al/Ag monochromatic X-ray source.
Room-temperature excitation and emission spectra for the samples were
obtained using a Hitachi F4600 fluorescence spectrometer.
2.2. Synthesis of ZnAPA
A mixture of H2APA (400 mg, 2.21 mmol), Zn(NO3)2⋅6H2O (800 mg,
2.69 mmol) was dissolved in DMF/H2O (80 mL, 1:1, v/v) in a 100 mL
glass vial, and then 8 mL dioxane had been added. The glass vial was
capped under autogenous pressure and placed in an oven at 70 ꢀC for
three days. After the resulting mixture was slowly cooled to room tem-
perature, the transparent rod-like crystals were harvested, then washed
with DMF and ethanol for several times, and dried in air.
3. Results and discussion
Compared with the reported synthetic procedures [41], here we
developed a new method to prepare the crystal of MOF ZnAPA at a
moderate temperature. Typically, solvothermal reaction of
Zn(NO3)2⋅6H2O, 5-aminoisophthalic acid (H2APA) in mixed solvents of
N,N-dimethylformamide (DMF), water and dioxane at 70 ꢀC yielded
transparent rod-like crystals of ZnAPA. Powder XRD of the as-obtained
MOF crystals suggests that the sample is isostructural to the simulated
Zn(APA)(H2O) without negligible impurity (Fig. S1). The single-crystal
X-ray structure analysis reveals that ZnAPA crystallizes in the mono-
clinic P21/n space group, and each Zn atom is four-coordinated with two
carboxylate oxygen atoms from two APA ligands and one nitrogen atom
from another APA ligand, and one oxygen atom from the coordinated
water molecule, and the coordinated geometry can be identified as a
distorted tetrahedral configuration (Fig. 1b). In turn, each APA ligand
employs its two carboxylate groups and one amino group to coordinate
with three Zn atoms, respectively (Fig. 1c). Obviously, there is an un-
coordinated carboxylic oxygen atom attaching on the ligand, which can
serve as a functional site to react with the oxyphilic metal ions. The
mononuclear ZnNO3 secondary structural unit of ZnAPA is linked into a
1D infinite chain along the b axis by carbon atoms. The chains are then
bridged orderly to form a 2D layered network through APA ligand
(Fig. 1d). Interestingly, such layered structure exhibits a pore with a size
of about 8.2 Å, which is large enough to accommodate guest ionic spe-
cies, thus enabling the recognition of guest ions via the host-guest
interaction. In addition, these porous 2D layers are connected through
hydrogen bonding interactions to form a 3D supramolecular network, as
shown in Fig. 1e. In order to investigate the stability of ZnAPA, the
2. Experimental
2.1. Materials and measurements
All solvents and reagents were of reagent grade quality purchased
from commercial sources and used without further purification. Ther-
mogravimetric (TG) analysis of the product was carried out on a Netzsch
TG209F3 instrument under N2 atmosphere from room temperature to
800 ꢀC with a heating rate of 10 ꢀC⋅min-1. Infrared (IR) measurements
were performed on a Thermo Fisher Nicolet iS10 spectrometer with
pressed KBr pallets in the range of 400–4000 cm-1 at room temperature.
UV–vis absorption spectra of the samples were recorded using a Hitachi
UH5300 spectrophotometer. Powder X-ray diffraction (PXRD) patterns
were recorded on an MAXima_X XRD-7000 diffractometer with Cu K
α
radiation (λ ¼ 1.542 Å) in 2θ range of 5–50o, with a step speed of 2o⋅min-
1. Single-crystal XRD measurements of ZnAPA was performed on a Bruker
APEX-II diffractometer using graphite-monochromatic Mo Kα radiation
(λ ¼ 0.71073 Å) and an CCD detector at 293 K. X-ray photoelectron
spectroscopy (XPS) was conducted on AXIS Supra x-ray photoelectron
Fig. 1. Single-crystal X-ray structure of ZnAPA, presenting (a) the organic ligand, 5-aminoisophthalic acid; (b) the coordination configure of Zn2þ as five-connected
nodes; (d) each ligand shows a four-connection model; (d) the 2D layered network; (e) 3D supramolecular network structure (Zn, cyan; C, grey; O, red; N, blue; H
atoms are not shown). (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)
2

J. Jiang et al.
Journal of Solid State Chemistry 283 (2020) 121153
Fig. 3. Competitive experiments of ZnAPA in sensing Hg2þ ions with the
interference of other metal ions (100 μM), the baby blue and organic columns
represent in the presence and absence of Hg2þ ions, respectively. (For inter-
pretation of the references to colour in this figure legend, the reader is referred
to the Web version of this article.)
sample in the solid state (Fig. S6), which can be attributed to the metal to
ligand charge transfer. By taking advantage of the ligand-based fluores-
cence of ZnAPA and the attached active sites for guest metal ions, this
material can be used for fluorescent detection of Hg2þ ions. To investi-
gate the ability of ZnAPA to detect a trace quantity of Hg2þ ions, the
suspension state fluorescence experiment was performed. Fig. 2a pre-
sents the fluorescence response of ZnAPA suspension solution (1 mg in 5
mL H2O) with different amounts of Hg2þ ions. With the increasing con-
centration of Hg2þ ions, the intensity of emission at 405 nm for ZnAPA
dramatically decreases; whereas at 100 μM, the intensity decreased by
75%. After that, the emission intensity decreases and the peak shows
slightly red-shift with the Hg2þ concentration raises. The emission of
ZnAPA was completely quenched when concentration of Hg2þ reach
~400 μM. Obviously, in the range of 0–100 μM, the fluorescence in-
tensity of ZnAPA and the concentration of Hg2þ ions delivers a good
linear relationship and the fitted curve follows an equation with a cor-
relation coefficient R2 ¼ 0.9926 and can be described as
I ¼ -69.81 CHg2þ þ 8819
I represent the fluorescence intensity of ZnAPA and C Hg2þ indicates
the concentration of Hg2þ ions. The limit of detection (LOD) can be
calculated using: LOD ¼ 3δ/S, where δ and S indicate the standard de-
viations for blank solutions of fluorescence intensity and the slope of the
fitted curve, respectively. Accordingly, the LOD value of ZnAPA towards
Fig. 2. (a) Fluorescence spectra of ZnAPA (1 mg) in water solution (5 mL) with
increasing amounts of Hg2þ (0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80,
90, 100, 120, 150, 180, 200, 250, 300, and 400
μM, respectively); (b) the
relationship of peak fluorescence intensity of ZnAPA and concentration of Hg2þ
ions in aqueous solution.
Hg2þ was determined to be 0.1243
reported probes [33,42,43].
μM, which is comparable to many
powder sample of ZnAPA was treated at different temperatures and
characterized by XRD measurement. From the obtained powder XRD
patterns (Fig. S3), ZnAPA was thermal stable after heat treating at 200 ꢀC
in air atmosphere. Moreover, the TG analysis experiments were per-
formed. As can be seen in the TG curve (Fig. S2), ZnAPA undergoes two
steps of weight loses in nitrogen atmosphere: the first mass loss stage, in
the range of 220–300 ꢀC corresponds to the loss of coordinated water
molecule; the second step occurred at 410–800 ꢀC is attributed to the
gradually collapse of the framework. This implies that the main crystal
framework can withstand the high temperature of 410 ꢀC, demonstrating
its good thermostability.
In order to investigate whether ZnAPA acts as a highly selective
fluorescent molecular probe for Hg2þ ion, interference experiment was
performed (Fig. 3). Some possible heavy metal ions in real wastewater
samples were selected, and added consecutively into the suspensions of
ZnAPA, respectively. Clearly, in presence of different kinds of metal ions,
including Agþ, Kþ, Naþ, Liþ, Cd2þ, Ca2þ, Mg2þ, Ni2þ, Zn2þ, Al3þ, and
Cr3þ, no significant fluorescence changes of ZnAPA were detected.
However, after adding Hg2þ ions into the ZnAPA solutions containing
these interfering metal ions, the fluorescence of ZnAPA quenched
immediately. Such results indicate that the Hg2þ induced fluorescence
response was unchanged in the environment of 1 equiv of other inter-
fering metal ions, suggesting that ZnAPA was a high selective probe for
Hg2þ recognition. In general, there are several factors could have con-
tributions to the high selectivity for Hg2þ, such as the suitable pore size of
the framework, the soft acidity, the conjugation of benzene, and the large
radius of the Hg2þ ions [30,31].
The excitation and emission spectra of the free ligand H2APA and as-
synthesized MOFs in the solid state were measured under room condi-
tions and shown in Fig. S5. Upon excitation at 316 nm, the ligand H2APA
exhibits a broad band centered at 416 nm, which is assigned to the π*-π
transition. Compared to free ligand, the emission of ZnAPA shows a
slightly red-shifted emission of the H2APA ligands around at 424 nm.
Interestingly, the compound ZnAPA in aqueous solution exhibits the
maximum emission at 405 nm and a blue shift of 19 nm compared to the
The mechanism of the Hg2þ-induced fluorescence quenching for
ZnAPA was further investigated. In theory, Hg2þ ions could readily
3

J. Jiang et al.
Journal of Solid State Chemistry 283 (2020) 121153
Fig. 5. Powder XRD patterns of ZnAPA measured after being immersing in tap
water, boiling water, PBS solution, pH ¼ 1 and 4 HCl solution, as well as pH ¼
10 NaOH solution for 2 days, respectively.
group and Hg2þ ions, the uncoordinated oxygen atoms of APA ligands
can serve as active sites to interact with Hg2þ ions, thus inhibiting the
intermolecular energy transfer and quenching the luminescence of
ZnAPA (Fig. S8). The fluorescence quenching mechanism was further
investigated by comparing the UV–vis absorption spectra of Hg2þ, ZnAPA
and Hg2þ-incorporated ZnAPA. Powder XRD results indicate that the
crystallinity and framework of ZnAPA was unchanged after soaking in
Hg2þ solution for 12 h (Fig. S9). By comparing the UV–vis absorption
spectrum of Hg2þ (Fig. S10) and the excitation spectrum of ZnAPA, one
can see that the excitation wavelength of ZnAPA was covered by the
absorption spectrum of Hg2þ ions. This result indicates that the Hg2þ ions
can adsorb the excitation energy of ZnAPA and influence the energy
transfer process in the ZnAPA.
In order to characterize the chemical stability of ZnAPA, the powder
samples were treated with tap water, PBS solution, HCl (pH ¼ 2, 4) and
NaOH (pH ¼ 10) aqueous solution at room conditions, as well as boiling
water for 2 days. After that, the measured PXRD profiles (Fig. 5) of these
samples show good crystallinity and integrated structures, suggesting the
superior stability of ZnAPA, comparable, even, to the classic UiO series
[44]. It is worth noting that there are very few Zn-based luminescent
MOFs possessing good chemical stability in PBS, boiling water and in
aqueous solution with a pH range from 2 to 10. Such as, the frameworks
based on paddle-wheel Zn2(COO)4 units are tend to hydrolysis in the
presence of water, and unstable in an acid/base solution [35–37]. The
extraordinary chemical stability of ZnAPA might stem from its special
structure, where four-coordinated Zn2þ subunits are more stable than
paddle-wheel units and the Zn–N(NH2) bonding interactions are stronger
than Zn–O(COOH) [38]. The high selectivity and superior chemical
stability features make the luminescent ZnAPA a potential candidate for
detection of Hg2þ ion in practical applications.
Fig. 4. XPS analysis of the O 1s peaks of ZnAPA before (a) and after (b) treated
with the aqueous solution of Hg2þ ions (100
μM).
chelate with some soft electron donor atoms, such as sulfur, nitrogen or
phosphorus, and hinder the energy transfer from the to * orbital
π
π
within the chromophore, thus quenching the fluorescence intensity.
However, it is necessary to point out that, in ZnAPA, the amino groups of
ligand APA are coordinated to the Zn2þ centers, and only uncoordinated
carboxylic oxygen atoms can serve as free-standing donors for guest Hg2þ
ions. To investigate the interactions between the functional site and Hg2þ
ions, X-ray photoelectron spectroscopy (XPS) was applied to analyze the
N 1s and O 1s peak of ZnAPA as well as Hg2þ-incorporated ZnAPA. The
high-resolution N 1s XPS spectrum of ZnAPA can be fitted into three
major peaks, as shown in Fig. S7. Specifically, the peak at 407.49 eV
corresponds to the bonding interaction between the N atom of the amino
group and Zn2þ ions. After treating with Hg2þ ions, this peak delivers a
blue shift of 0.31 eV, which indicates that the coordinated N atom of the
amino group have affinity interactions with guest Hg2þ ions [30,31]. As
shown Fig. 4a, O 1s of ZnAPA can be fitted into two peaks at 531.90 eV
and 533.30 eV, respectively assigned to the free hydroxyl oxygen and the
carbonyl oxygen. In the presence of Hg2þ, the O 1s peak at 533.30 eV was
shifted to 533.17 eV (Fig. 4b), suggesting the bonding interaction be-
tween the uncoordinated oxygen and Hg2þ. These results indicate that in
addition to the affinity interactions between the N atoms of the amino
4. Conclusions
In summary, the monocyclic ligand 5-aminoisophthalic acid, with
multi-coordination groups, was used to construct the acid-based resistant
MOFs with Zn2þ ions. The as-synthesized MOF ZnAPA was characterized
by means of single-crystal XRD, powder XRD, FTIR, and TG analysis. Our
results show that ZnAPA features high selectivity and favorable limit of
detection to the Hg2þ in aqueous solution. The possible mechanism of the
Hg2þ-induced fluorescence quenching for ZnAPA was discussed in detail.
Most importantly, ZnAPA shows extraordinary chemical stability in PBS
buffer solution, boiling water and in aqueous solution with a pH range
4

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