Two uranyl heterocyclic carboxyl compounds with fluorescent properties as high sensitivity and selectivity optical detectors for nitroaromatics

Article abstract of DOI:10.1039/C6NJ03933B

The two compounds UO₂(C₁₆H₇N₄O₄)₂·2H₂O (1) and UO₂(C₂₀H₁₂N₅O₂)₂ (2) have been synthesized, based on the differen

Full text of DOI:10.1039/C6NJ03933B

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ISSN 1144-0546
PAPER
Jason B. Benedict et al.
The role of atropisomers on the photo-reactivity and fatigue of
diarylethene-based metal–organic frameworks
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Two Uranyl Heterocyclic Carboxyl Compounds with Fluorescent
Properties as High Sensitivity and Selectivity Optical Detectors for
Nitroaromatics
Received 00th January 20xx,
Accepted 00th January 20xx
Shuang Li,a Li Xian Sun,b Jue Chen Ni,a Zhan Shi,c Yong Heng Xing,*a Di Shang,a Feng Ying Bai*a
DOI: 10.1039/x0xx00000x
ABSTRACT: The two compounds, UO2(C16H7N4O4)2·2H2O (1) and UO2(C20H12N5O2)2 (2) have been synthesized, based on the
different heterocyclic carboxyl ligands, 2,3-pyrazino[1,10]phenanthroline-2,3-dicarboxylic acid (H2L1) and 2,6-bis(2-
pyrazinyl)pyridine-4-benzoic acid (HL2). Two compounds were characterized by the elemental analysis, IR spectroscopy,
PXRD, thermogravimetric analysis and UV-vis Spectroscopy. The single crystal X-ray diffraction analysis revealed that both
compounds 1 and 2 exhibited 2D sheet structures. Moreover, the study of fluorescence quenching properties of
compounds 1 and 2 showed that the luminescent intensity decrease for both 1 and 2 were especially obvious with the
increasing of the nitroaromatics concentration, even if the nitroaromatics were at a very low concentration (for 1 is 15
ppm, for 2 is 20 ppm), which can also be detected. The experimental results suggest a high selective quenching of initial
fluorescence intensity in the presence of nitroaromatic compounds. And by calculating the quenching constants of the
nitroaromatics using the SV equation (I0/I) = KSV[A] + 1, we can see the KSV values of the quencher TNP are both largest for
two compounds, and the values are 1.6×106 and 8.5×105 for 1 and 2, respectively. It means that the two compounds are
of the best sensitive luminescence. In addition, compound 2 exhibit enhanced fluorescence behavior towards to aldehyde
compounds, showing a turn-on fluorescence responsive behavior.
www.rsc.org/
dinitrobenzene (DNB), etc., which are the main ingredients of
explosives, and they also are classified as plastic explosives.9,10
Among all of the nitroaromatics, 2,4,6-trinitrophenol (TNP) is
Introduction
The rapid and selective detection of high energetic chemicals
have become a major concern, which due to the increasing use
of explosive materials.1-4 Therefore, the development of
simple, inexpensive and rapid detection methods of trace
explosive materials has become very important, that is mainly
applied in the fields of homeland security, environmental
implications and so on.3b,5-7 As we known, nitroaromatics, one
of the most important chemical intermediates, have been
widely used for dye, pharmaceuticals, fluorescent probes and
pesticide in recent years.8 Moreover, nitroaromatics remain as
key energetic materials for the preparation of landmines and
improvised explosive devices (IED).5a Nitroaromatics include
2,4,6-trinitrophenol (TNP), 2,4,6-trinitrotoluene (TNT), 2,4,6-
trinitrobenzene (TNB), 2,4-dinitrotoluene (DNT), and 1,3-
one of the most dangerous chemicals and its explosive nature
is even stronger than 2,4,6-trinitrotoluene (TNT), and TNP has
been used as an important ingredient of explosives and rocket
fuels.8b,11,12 Beside these, TNP is used in glass, match,
fireworks, dye, and lather industries.8c
However, the
nitroaromatics are well-known as the highly toxic contaminant
with broad range of detriment, and TNP also causes
unpleasant effects on human health such as irritant to skin/eye
and damage the respiratory system.11b,13 Moreover, aldehydes
are great harm for our health. Therefore, the highly sensitive
and selective detection of nitroaromatics and aldehydes are of
high significance. Up to now, many methods have been
reported, such as canines and sophisticated instrumental
methods, for nitroaromatics detection are inconvenient and
not always available.14 And as we known, fluorescence sensing
is the change of the interaction between the molecules and
the fluorescence signal; the aim is to achieve special
recognition of certain molecules or ions. The fluorescence
signals are including fluorescence enhancement or quenching,
the change of fluorescence characteristic peak position,
change of fluorescence lifetime and change of fluorescence
polarization, and so on. Thus, to solve these problems, optical
detection method is attracting increasing attention because of
their high simplicity, sensitivity and quick response time, and
the design of coordination polymers/metal–organic
a.College of Chemistry and Chemical Engineering, Liaoning Normal University,
Huanghe Road 850#, Dalian 116029, P.R. China.
E-mail: xingyongheng2000@163.com, baifengying2000@163.com
b.Guangxi Key Laboratory of Information Materials, Guilin University of Electronic
Technology, Guilin 541004, P.R. China.
c. State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of
Chemistry, Jilin University, Changchun 130012, P.R. China.
† Electronic supplementary informaꢀon (ESI) available: Figures of Infrared spectra,
figure of structure, TG analyses, PXRD, UV-vis Spectroscopy, band gap and the
bond lengths (Å) and angles (°) are presented in the supplementary material. CCDC
1491331-1491332. See DOI: 10.1039/x0xx00000x
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frameworks based luminescence detectors for nitro explosives
has been developing rapidly.15,16 Compared with the huge
amount of 3d and 4f metal–organic frameworks, 5f actinide
compounds that adopt more various topologies and
coordination geometries have been less investigated.
Recently, the chemistry of actinide mixed materials has
attracted more and more attention. Moreover, uranyl–organic
assemblies have received considerable attention not only due
to the diverse chemical compositions and architectures, but
also have a wide range of important physicochemical
properties that include ion exchange, ionic conductivity,
intercalation chemistry, photochemistry, nonlinear optics,
selective oxidation catalysis and so on.17-19 In the past
literatures, we could see that, the uranium metals always
coordinated with oxygen atoms from the ligands.20 And the
uranium exhibits an interesting chemical ability to successfully
form an abundant variety of frameworks with different
network dimensionalities through 4–6 additional coordination
sites in the equatorial plane (4+2, square bipyramid; 5+2,
pentagonal bipyramid; 6+2, hexagonal bipyramid), and the
central metal uranium coordinated with the nitrogen atoms
(N) from the N-heterocyclic ligands makes the compound
structures and properties more abundant.21
(b)
Scheme 1. The molecular structures of (a): H2L1, (b): HL2.
Experimental
Caution! While all the uranyl compounds used in these studies
contained depleted uranium salts, standard precautions were
performed for handling radioactive materials, and all studies were
conducted in a laboratory dedicated to studies on actinide elements.
Materials and Methods. All chemicals purchased commercially
were of reagent grade or better and used without further
purification (Sinopharm Chemical Reagent Co., Ltd.). Elemental
analyses of C, H, and N were conducted on a Perkin-Elmer 240C
automatic analyzer at the analysis center of Liaoning Normal
University. All IR measurements were obtained using a Bruker AXS
TENSOR-27 FT-IR spectrometer with pressed KBr pellets in the
range of 400–4000 cm-1 at room temperature. UV-vis-NIR spectra
for two compounds, and the ligands (H2L1 and HL2) were recorded
on a JASCO V-570 UV/VIS/NIR microspectrophotometer (200-2500
nm, in the form of solid sample). Thermogravimetric analysis (TG)
was performed on a Perkin Elmer Diamond TG/DTA under the
conditions of the N2 atmosphere in the temperature range from 30
to 1000 °C. X-ray powder diffraction patterns were obtained on a
Bruker Advance-D8 equipped with Cu Ka radiation, in the range 5° <
2θ < 55°, with a step size of 0.02° (2θ) and an count time of 2s per
step. The photoluminescent properties of the compounds 1 and 2
were measured in the solid state and in different solvent emulsions
on a JASCO FP-6500 spectrofluorimeter at room temperature. The
electrode is made of optical glass coated with indium and tin oxides
(ITO). Standard p-type silicon flakes were used to adjust the
comparative phase, and a xenon lamp was used as an Illuminator to
supply radiation in the range of 300–800 nm.
Herein, we have utilized two different heterocyclic carboxyl
ligands, 2,3-pyrazino[1,10]phenanthroline-2,3-dicarboxylic acid
(H2L1) and 2,6-bis(2-pyrazinyl)pyridine-4-benzoic acid (HL2), the
molecular structures are shown in the Scheme 1, to react with
UO2(CH3COO)2
compounds, UO2(C16H7N4O4)2
) under the hydrothermal condition, respectively. The two
·
2H2O, and constructed two the new
·
2H2O ( ) and UO2(C20N5O2H12)2
1
(
2
compounds were characterized by single-crystal X-ray
diffraction, IR spectra, UV-vis spectra, XRD analysis and the
thermal properties. What’s more, we have researched the
mechanism of quenching mechanism, selectivity and
sensitivity of different nitroaromatics through the two
compounds as substrates in detail.
Synthesis
The ligand HL2 (HL2= [2,6-bis(2-pyrazinyl)pyridine-4-benzoic acid])
was synthesized according to the method described in the
literature.22 The solution of 2.0 mol/L sodium hydroxide (50 ml)
was added into the mixing solution of acetylpyrazine (3.260 g，
26.7 mmol) and 4-Carboxybenzaldehyde (4.035 g, 26.7 mmol) in the
50ml ethanol at 0–5 oC under stirring by dropwise. Then, the
mixture continued to react for 2 h at 0–5 oC, then added
(a)
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monochromatized Mo Kα radiation (λ
semiempirical absorption correction was applied by the program
SADABS.23
The program suite was used for space-group
determination (XPREP), direct method structure solution (XS), and
least-squares refinement (XL).24
Crystal data and structure
=
0.71073 Å).
A
refinement parameters are given in Table 1, the main selected bond
lengths and angles of compounds 1 and 2 are listed in the Table S1.
UO2(HL1)2·2H2O (1) (L1=C16N4O4H6). As illustrated in Figure 1a, the
asymmetric unit in compound 1 consists of one crystallographically
independent one uranyl ion, one incompletely deprotonated ligand
and one aqua ligand. The uranyl oxygen atom at the apexes are
bonded to the central uranium atom (U1) at the distance of 1.760(3)
Å and the O=U=O bond angles is 179.99(2)° to form the near-linear
[UO2]2+ cation, in good agreement with the reported average uranyl
bond length and angle.25 Six equatorial positions of U1 are
occupied by oxygen atoms from three chelating carboxylate groups
pertaining to three ligands from different directions. As described
above, the whole ligand acts as a μ3-bridge linking two UVI centers
as illustrated in Figure 1b. And the N3 has been protonated in this
structure. Intriguingly, the adjacent uranyl polyhedra are linked by
carboxyl groups of H2L1 ligand to form secondary building units
(Figure 1c) and further form infinite one dimensional chains by the
ring of the ligand (Figure 1d). The inorganic chains linked by the
hydrogen bonds of C1-H1···O4A and N3-H3A···O2 to furthermore
form a 2D network structure of compound 1 (Figure 1e), and the
hydrogen bonds of O5-H5···O1 make the 2D structure more stable.
Scheme 2. The ligand HL2 synthesis process.
acetylpyrazine (3.260 g， 26.7 mmol) and ammonium acetate (10 g,
129.7 mmol) to continue reaction. The mixture was heated to
reflux at 100 oC for another 3 h. After cooling to room temperature,
the white solid was collected by filtration, then, the white powder
was recrystallized with ethanol and filtration. The yield of the
product was 65%. The ligand HL2 synthesis process was shown in
the Scheme 2. IR data (KBr, cm-1): 3408(s, br), 3216(s), 1708(m),
1597(s), 1566(s), 1404(w), 1273(s), 1161(w), 1120(w), 1060(m),
1029(m), 898(m), 848(m), 787(w), 706(w), 574(w), 473(w). And the
IR spectrum was shown in the Figure S1.
UO2(HL1)2·2H2O (1) (L1=C16N4O4H6). Compound 1 was synthesized
from combining UO2(CH3COO)2·2H2O (0.042 g, 0.100 mmol), H2L1
(0.008 g, 0.025 mmol), demineralized water (6 mL) and ethanol (3
ml) in glass vessel and stirred for 4 h at room temperature. The
yellow suspension with a pH of 4 was put in a 23 mL Teflon-lined
stainless steel autoclave and heated statically at 120 °C for 3 days,
then allowed to crystallize over 2 days at room temperature.
Yellow single crystals were obtained from the resulting solution,
which could be isolated with a yield of 45% based on [UO2]2+ after
filtration and washing thoroughly with distilled water. Elemental
Analysis (%) Calcd for compound 1, C32H18N8O12U: C, 40.65; H, 1.91;
N, 11.86. Found: C, 40.53; H, 1.78; N, 11.86. IR data (KBr, cm-1):
3401(m, br), 2923(w), 2853(w), 1744(w), 1605(s), 1530(w), 1417(m),
1362(m), 1271(w), 1208(w), 928(s), 646(w), 544(w).
UO2(L2)2 (2) (L2=C20N5O2H12). The structure of 2 comprises one
crystallographically distinct UVI center and one ligand (HL2) in the
Figure 2a. The uranium atom is eight-coordinated by two atoms
with an O=U=O angle of 180.0° and a bond length of 1.746(3) Å,
four oxygen atoms from the carboxyl group of two ligands with the
bond distances in the range of 2.440(3) Å to 2.474(3) Å, respectively,
and two nitrogen atoms from the two ligands with the bond length
of 2.699(3) Å, forming a distorted hexagonal bipyramid geometry.
As shown in the Figure 2b, two coordination modes of the
carboxylate groups in the ligand are observed: chelating bidentate
(μ1-η1η1) and monodentate (μ1-ηN1). In the extended configuration,
each building block [UO2(COO)2N2] connects with four ligands HL2,
in the meantime, each ligand is connected with the two building
blocks, to form a two-dimensional structure. As shown in the
Figure S2, the hydrogen bonds of C4-H4···N3 make the 2D structure
more stable.
UO2(L2)2 (2) (L2=C20N5O2H12). The synthesis of compound 2 was
similar to that of 1, the only difference was that the ligand HL2
(0.008 g, 0.0230 mmol) was in place of H2L1. And yellow single
crystals were obtained from the resulting solution, which could be
isolated with a yield of 43% based on [UO2]2+ after filtration and
washing thoroughly with distilled water. Elemental Analysis (%)
Calcd for compound 2, C40H24N10O6U: C, 49.04; H, 2.45; N, 14.30.
Found: C, 48.91; H, 2.37; N, 14.41. IR data (KBr, cm-1): 3471(w, br),
3072w), 1815(m), 1712(w), 1595(m), 1522(m), 1435(s), 1131(m),
1021(m), 919(s), 849(w), 722(w), 480(w).
Infrared Spectroscopy.
The IR spectra of compounds 1 and 2 were shown in Figure S3. The
broad absorption bands appearing at 3401 cm-1 of compound 1
indicates the presence of water molecules (for 2, at 3470 cm-1
maybe hydroxy peak of ethanol). For 1, the peak around 2923 cm-1
is attributed to the –CH2– stretching mode (for 2 at 3072 cm-1).
Absorption at 1605, 1417 cm-1 of 1 and 1595, 1435 cm-1 of 2 are
assigned to the asymmetrical stretching vibration and symmetrical
stretching vibration of C=O bond, respectively. The bands between
1400–1600 cm−1 are attributed to the skeletal vibrations of the
organic aromatic rings. And for 1, the symmetric and asymmetric
stretching modes of U=O is observed at about 928 cm−1 (919 cm−1
for 2).
RESULTS AND DISCUSSION
X-ray Crystal Structure Determination and Structural Descriptions.
Single crystals of suitable dimensions for compounds 1 and 2 were
mounted on glass fibers for the X-ray structure determinations.
Reflection data were collected at room temperature on a Bruker
AXS SMART APEX II CCD diffractometer with graphite
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Table 1. Summary of crystal data and refinement results for
Journal Name
different weight loss process, compared with
1, there is no
compounds 1 and 2*
lattice water molecule in compound 2, the first loss-weight is
observed at 114°C and completed at 505 °C, which can be
attributed to the loss of uranium metals connected with
atriazine rings (obs: 27.25%; calcd: 27.38%). From then on, as
the temperature increases, the skeleton continues to
furthermore collapse. The final remaining is that UO3 with
carbon residue (obs: 48.12%; calcd: 46.39%).
1
2
Chemical formula
M(g mol–1)
Crystal system
Space group
a(Å)
C32H18N8O12U
944.57
Triclinic
C40H24N10O6U
978.72
Monoclinic
P21/c
－
P1
PXRD analysis.
7.3139(7)
9.6308(9)
11.2039(10)
73.572(2)
78.457(2)
73.711(2)
720.31(12)
1
9.2837(6)
25.2187(17)
7.4546(5)
90
In order to confirm whether the crystal structures were truly
representative of the bulk materials, the PXRD patterns of the
b(Å)
compounds
1 and 2 were recorded, as shown in the Figure S5.
c(Å)
Compared with the corresponding simulated single-crystal
diffraction data, all the peaks present in the measured
patterns closely match in the simulated patterns generated
α
(deg)
(deg)
(deg)
β
95.4780(10)
90
from single crystal diffraction data, which indicates that
are in pure phases.
1 and
γ
2
V(Å3)
1737.3(2)
2
UV-vis Spectroscopy.
Z
The diffuse reflectance UV-vis spectra of compounds
1 and 2
Dcalc(Mg m–3
)
2.178
1.871
are shown in the Figure S6. Compounds
1 and 2 all presented
Crystal size(mm)
0.30 × 0.25 × 0.18 0.45 × 0.39 × 0.28
four peaks, and for 1, the three absorption peaks appearing at
about 211, 262 and 323 nm are associated with the π→π*
transition of the ligand, which are similar to the absorbance
F(000)
454
948
ꢀ
(Mo–Kα) mm–1
(deg)
5.723
4.739
spectra of the corresponding ligands (H2L1 and HL2), (for
three absorption peaks appearing at about 215, 265 and 338
nm). And the characteristic equatorial U O charge transfer
band and axial U-O charge transfer band (vibrative coupling)
are observed around 429 nm for both compounds and . In
2, the
θ
1.91 to 25.00
3728
2.20 to 27.88
10864
–
Reflections collected
Independent
reflections
2523 (2461)
4053 (2560)
1
2
addition, according to UV spectra of the compounds, we
calculated the band gap of the ligands (H2L1 and HL2) and the
two compounds (Figure S7). The values are 3.14, 3.29, 2.98,
2.89 eV, respectively. From these data, we can see that the
band gaps of the ligands are bigger than that of theirs
corresponding compound, which show furthermore the
existence of electronic transitions from the ligand to the metal.
Parameters
261
259
Rint
0.0176
0.0380
ꢁ(ρ)(e Å–3
)
0.975 and -1.556
1.068
1.107 and -0.926
1.009
Goodness of fit
Ra
0.0271 (0.0294)b
0.0310 (0.0671)b
0.0589 (0.0670)b
[Σw(Fo2–Fc2)2/Σw(Fo2)2]1/2
;
a
wR2
0.0571 (0.0582)b
Photoluminescent (PL) properties and nitroaromatics
detections.
a
*
R
= ΣFo– Fc/ΣFo, wR2
=
Fo>4σ(Fo). b Based on all data.
The fluorescence of inorganic–organic compounds has been
currently drawing significant attention in the development of
fluorescent materials. The luminescent properties of UVI are of
interest due to potential applications including photocatalysis.
The utilization of [UO2]2+ ions in compounds arranges the
metal centers into an extended topology as well as allows for
the introduction of chromophoric organic linkers, which could
sensitize the [UO2]2+ luminescence. As we known, the
luminescence of uranyl compounds was at near 520 nm.
However, not all uranyl compounds possess luminescent
properties, and the mechanisms of the emission from uranyl
compounds are most often difficult to explain. As shown in
the Figure 3a, we can see that compound 1 (λex = 351 nm) has
a five-peak spectrum, and the five-peak spectrum has been
red-shift, compared with the fluorescent of the benchmark
Thermal properties.
To examine the thermal stability of the compounds,
thermogravimetric analysis (TG) was carried out. And the
thermalgravimetric curves of compounds
1 and 2 are shown in
Figure S4. For 1, the first loss-weight is observed at 30 °C and
completed at 320 °C, which is in good agreement with the loss
of two lattice water molecules (obs:2.22%, calcd:3.81%). The
second loss-weight is observed at 321 °C and completes at
710 °C, which is in good agreement with the decomposition of
the two chelating carboxyl groups (obs: 11.91%; calcd: 9.32%).
The final remaining weight is 86.1%, which is in good
responding to the formation of U3O8 (calcd 89.1%). And the
compound UO2(CH3COO)2
·
495, 517, 541 and 567 nm) for
2H2O (λex = 420 nm). Five peaks 482,
and five peaks (475, 490, 511,
thermogravimetric curve of compound
2
exhibited that a
1
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535 and 561 nm) for UO2(CH3COO)2
·
2H2O, are observed in the
spectra, which all exhibit characterized emission from uranyl
cations. And the emission peak of 364 nm is from the ligand
(H2L1) in the compound
1. For 2, due to the conjugative ligand
H1L2, it exhibits strong a broad emission peak at 398 nm λex
=
290 nm), which is assigned to the π*→n or π*→π transition
(Figure 3b), compared with the fluorescent of the ligand
H1L2(λex = 290 nm). And, another obvious emission peak is at
516 nm, which can be alleged the absorption peak of the
uranyl cations, which may be attributed to change electron
cloud intensity of the central ring due to coordination with
metals.
Based on characterized emission information from uranyl cations,
we explored the potential sensing ability of 1 and 2 to sense a trace
amount of nitroaromatics; luminescence quenching titrations were
Figure 1. For
1, (a) Perspective view of the coordination
10000
environment around the uranium atom, symmetry codes: A, -
1+x, y, z; B, 1-x, 1-y, -z; C, -x, 1-y, -z. (b) Coordination
schematic diagram of ligand, symmetry codes: D, 1+x, y, z. (c)
UO (CH COO)
2
3
2
compound 1
8000
6000
4000
2000
0
The building block of compound
and one uranyl bipyramidal polyhedron. (d) The one-
dimensional chain structure of compound (e) The 2D
structure of the Some hydrogen atoms and solvent
molecules are omitted for clarity.
1
formed by four H1L1− ligands
1.
1.
400
500
600
Wavelength (nm)
(a)
Figure 2. For
2, (a) Perspective view of the coordination
environment around the uranium atom, symmetry codes: A,
1+x, 0.5-y, -0.5+z; B, 2-x, -0.5+y, 0.5-z; C, 3-x, -y,-z. (b)
Coordination schematic diagram of ligand, symmetry codes: B,
2-x, -0.5+y, 0.5-z. (c) The building blocks linked with four
(b)
Figure 3. (a) Luminescent spectra of UO2(CH3COO)2
420 nm), and compound
Luminescent spectra of the ligand H1L2(λex = 290 nm), and
compound (λex = 290 nm) in the solid state.
·
2H2O(λex
=
1
(λex = 351 nm) in the solid state; (b)
ligands. (d) The 2D structure of the 2. Hydrogen atoms and
solvent molecules are omitted for clarity.
2
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performed with an incremental addition of nitroaromatics to the high sensitivity in detecting small amounts of nitro groups in
compounds 1 and 2 dispersed in the deionized water. First, we solution compared with most reported compounds, and the
clean the compounds, dry, and making them grinded good. Then, observed KSV values are large, which showed that the both
taking 2 mg from grinding samples 1 and 2, respectively, and compounds 1 and 2 have a higher sensitivity.28 In the Table 3, we
immersed in the corresponding solvents (3 mL). After treated by chose the TNP and DNT as the better quenchers compared with the
ultrasonication for 30 minutes, the samples were suspended in relevant literature. From it, we can see that the quenching effect is
different solvents and change into emulsions.
A series of close, and in the solvent, we choose environmentally friendly and
nitroaromatics solvents include 2,4,6-Ttrinitrophenol (TNP), 2,4- non-toxic water as the solvent. From the comparison of KSV values,
dinitrotoluene (DNT), p-Nitroaniline, m-Dinitrobezene, sodium we can see that the both two compounds have better sensitivity
nitrobenzene sulfonate, nitrobenzene (NB) and non-nitro benzene and selectivity. Moreover, we take 50ppm suspension with
(B). The optimum conditions are at about 25 °C and the solution different quenchers, which mixing compound 1 or 2, respectively,
solubility good, and the solution concentration and solution then, and UV absorption were tested by UV spectra after the
solubility directly affect the experimental results, so we must centrifugation. As shown in the Figure 7, we can see that the
control the temperature, concentration, solubility and other issues highest UV absorption is TNP for 1 (for 2, UV absorption is shown in
in the course of the experiment. The two compounds dispersed in the Figure S13). And as shown in the Figure 8, there is some
deionized water exhibited strong emission in visible region upon overlap between the absorption spectra of quenchers and the
excitation at 351 and 290 nm, respectively. To explore the ability of compounds, and different degree of overlap may also explain why
the two compounds to sense a trace amount of nitroaromatics, the different quenchers quenching effect are different.
determination of fluorescence quenching was performed with an
What’s more, the homogeneous dispersible nature of the
incremental addition of nitroaromatics to the two compounds
submicron sized uranium–organic materials has enabled a
dispersed in deionized water. Here, we take the compound 1 as the
close contact between the compounds and the nitroaromatics.
main example to research the mechanism of the nitro quenching
The most important factor of the dynamic quenching maybe
mechanism, selectivity and sensitivity. As shown in the figure 4a,
due to that the nitroaromatics with electron-deficient property
we can see the changes in the luminescence intensity with the
can obtain an electron from excited state of the ligand. In
increasing addition of TNP (up to 1000 ppm), and the quenching
other words, the excited state electrons can transfer from
efficiency is nearly 89% of the initial luminescence intensity for 1.
UOFs to nitroaromatics, which lead to luminescence
quenching.30 And the nitroaromatics with electron-deficient
For 2, the quenching efficiency is nearly 81%, and luminescence
quenching of 2 dispersed in H2O by gradually increasing TNP
can obtain an electron from excited state of the ligand, which
concentration was shown in the Figure S8a. Furthermore, in order
has been confirmed by molecular orbital theory. The LUMO of
to determine the detection limit of the TNP, we chose the ultra-low
nitroaromatics is a low-lying π*-type orbital stabilized by -NO2
concentrations of TNP to study luminescent response. For 1, we
through conjugation effect, so it should be lower than LUMO
can see that the fluorescence quenching can still be detected, when
of the ligand, which can also explain the mechanism of nitro-
quenched.31 And as we known, electron-transfer or energy
the concentration of TNP was as low as 15 ppm, as shown in the
Figure 4b. And for 2, the minimum quenching concentration of TNP
transfer between the compounds and the quenchers account
is at 20 ppm in the Figure S8b. Similar luminescence quenching was
for the fluorescence quenching of the compounds. So, the
also performed with other nitroaromatics such as 2,4-
main quenching mechanism for quenchers may be an excited
dinitrotoluene (DNT), p-Nitroaniline, m-Dinitrobezene, sodium
state charge transfer between the excited state of the
compounds and the ground state of the quenchers.32
nitrobenzene sulfonate, nitrobenzene (NB) and benzene (B) (Figure
S9a-f for 1 and Figure S10a-f for 2). Among these, we found that
Aldehydes detections.
show the similar luminescence quenching behaviour comparable to
the TNP except the benzene (Figure 5 and Figure S11). These In addition, we studied the fluorescence response of compound 2
results indicate that both the two compounds are effective towards to formaldehyde and benzaldehyde molecules at ultra-low
detectors for nitroaromatics. In the whole testing process, the concentrations, the experimental methods are similar to the
experimental method is relatively simple and fast, the amount of fluorescence test methods of compounds towards to nitroaromatics.
solution required is relatively small, test time for each sample is Taking 2 mg from grinding sample 2 and then immersed in the
about 30s, which can save our time.
corresponding concentration of the ethanol solution (3 mL). After
treated by ultrasonication for 30 minutes, the samples were
completely dissolved. The compound 2 dispersed in ethanol
exhibited strong emission in visible region upon excitation at 290
nm. As shown in the Figure 9, we could see that with the increase
of the concentration of the aldehyde, the fluorescence intensity is
also enhanced. This showed a turn-on fluorescence responsive
behavior, which may be interpreted as the ligand and aldehyde to
To understand the sensitivity and selectivity, the Stern–Volmer
plots were used to calculate the quenching constants of the
nitroaromatics (Figure 6a and Figure S12a) using the SV equation
(I0/I) = KSV[A] + 1, where I0 and I are the luminescence intensities
before and after the addition of the nitroaromatics, [Q] is the molar
concentration of the nitroaromatics, and KSV is the quenching
constant.26,27 Different quenchers have varying degrees of impact
on the compounds are shown in the Figure 6b and Figure S12b.
And as shown in the Table 2, we can see that the KSV values of the
quencher TNP are largest for both two compounds, indicating their
form
a π*-π conjugation, and the π*-π conjugation work
synergistically to impede the rotation-induced energy dissipation,
and making the rigid skeleton strengthened, so the fluorescence
enhanced.33
6 | J. Name., 2012, 00, 1-3
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2500
2000
1500
1000
500
0 ppm
50 ppm
100 ppm
200 ppm
400 ppm
600 ppm
800 ppm
1000 ppm
0
450
500
550
600
Wavelength (nm)
(a)
(a)
1.35
1.30
1.25
1.20
1.15
1.10
1.05
1.00
0.95
10
8
TNP
DNP
p-Nitroaniline
m-Dinitrobezene
sodium nitrobenzene sulfonate
NB
6
Detection Limit
4
2
0
0
10
20
30
40
50
0
200 400 600 800 1000
Concentration(ppm)
Concentration(ppm)
(b)
(b)
Figure 4. (a) Luminescence quenching of 1 dispersed in H2O by
gradually increasing TNP concentration; (b) the detection limit of
TNP for 1.
Figure 6. For 1, (a) linear relationships of the quenching are
fluorescence intensity ratio and quencher concentration; (b) at
different concentrations, the value of the fluorescence intensities
and the quencher ratios.
1.0
TNP
DNT
TNP
DNT
p-Nitroaniline
m-Dinitrobezene
Sodium nitrobenzene sulfonate
NB
1.6
p-Nitroaniline
m-Dinitrobezene
Sodium nitrobenzene sulfonate
NB
0.8
1.2
0.8
0.4
Benzene
0.6
0.4
0.2
0.0
0
200
400
600
800 1000
0.0
Concentration(ppm)
200 250 300 350 400 450 500
Wavelength (nm)
Figure 5. Plot of fraction of luminescence intensity of 1 vs.
concentration of analytes, I0 and I are the luminescence intensities
in the absence and presence of nitroaromatics, respectively.
Figure 7. UV absorption of different quenchers with compound 1:
TNP, DNT, p-Nitroaniline, m-Dinitrobezene, Sodium nitrobenzene
sulfonate and NB, respectively.
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Table 2. Different quenchers’ KSV of the compounds 1 and 2.
Journal Name
0
4800
4000
3200
2400
1600
800
2uM
4uM
6uM
8uM
10uM
Analyte
1 [KSV(M-1)]
1.6×106
1.3×106
7.4×105
3.7×105
3.5×105
2.3×105
2 [KSV(M-1)]
8.5×105
3.9×105
4.1×105
4.8×105
4.4×105
3.6×105
TNP
DNT
m-Dinitrobezene
NB
350
400
450
500
550
Wavelength(nm)
p-Nitroaniline
sodium nitrobenzene
sulfonate
(a)
4000
3200
2400
1600
800
0
2uM
4uM
6uM
8uM
10uM
2.0
1.6
1.2
0.8
0.4
0.0
compound 1
compound 2
TNP
DNT
pꢀNitroaniline
mꢀDinitrobezene
Sodium nitrobenzene sulfonate
NB
350
400
450
500
550
Wavelength(nm)
(b)
200 240 280 320 360 400 440 480
Figure 9. (a) Luminescence enhancement of 2 dispersed in ehanol
by gradually increasing formaldehyde concentration; (b)
Luminescence enhancement of 2 dispersed in ehanol by gradually
increasing benzaldehyde concentration.
Wavelength (nm)
Figure 8. UV absorption of two compounds and different
quenchers.
Table 3. Comparison of data about different compounds for the detection of nitroaromatics.
Quenching
Quenchers
TNP
Compounds
Ksv’s value(M-1)
Solvent
References
efficiency(%)
The guest free Tb@1 (Tb@1’)
[Cd4(μ3-O)(TTHA)(H2O)2]·3H2O
UO2(HL1)2·2H2O (1)
UO2(L2)2 (2)
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acetonitrile
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H2O
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[Cd(HL1)(L2)]
DMF
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[Cd4(μ3-O)(TTHA)(H2O)2]·3H2O
UO2(HL1)2·2H2O (1)
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8 | J. Name., 2012, 00, 1-3
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crystal analysis, both compounds
structure. The luminescence studies reveal that compounds
and display selectivity and sensitivity to nitroaromatics in
deionized water. The results show that and may be used
for nitroaromatics sensing application. In addition, compound
showed a turn-on fluorescence responsive behavior towards
to aldehyde compounds. In summary, the successful
syntheses of the two compounds and the finding of their
unusual physicochemical properties may also help to explore
new types of sensing materials and detect the trace of
explosive materials.
1 and 2 exhibited a 2D sheet
1
2
1
2
2
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We are grateful for support provided by the National Natural
Science Foundation of China (Grant Nos. 21571091,
21371086), Guangxi Key Laboratory of Information Materials,
Guilin University of Electronic Technology, P. R. China (Grant
No. 151002-K), and State Key Laboratory of Inorganic Synthesis
and Preparative Chemistry, College of Chemistry, Jilin
University, Changchun 130012, P.R. China (Grant No. 2016-02).
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10 | J. Name., 2012, 00, 1-3
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Two Uranyl Heterocyclic Carboxyl Compounds with Fluorescent Properties as
High Sensitivity and Selectivity Optical Detectors for Nitroaromatics
Shuang Li,a Li Xian Sun,b Jue Chen Ni,a Zhan Shi,c Yong Heng Xing,*a Di Shang,a Feng Ying
Bai*a
a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian City,
116029, China. E-mail: xingyongheng2000@163.com, baifengying2000@163.com
b Guangxi Key Laboratory of Information Materials, Guilin University of Electronic Technology,
Guilin 541004, P.R. China.
c State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry,
Jilin University, Changchun 130012, P.R. China
Uranyl skeleton compounds showed strong sensitivity and selectivity for the detection of
nitroaromatic.