A novel AIE chemosensor based on a coumarin functionalized pillar[5]arene for multi-analyte detection and application in logic gates

Article abstract of DOI:10.1039/d0nj01343a

Aggregation induced emission (AIE) active molecules are widely applied for multi-analyte detection due to their unique advantages over conventional fluorescent probes. Herein, a novel coumarin functionalized pillar[5]arene (PX) has been designed and synth

Full text of DOI:10.1039/d0nj01343a

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DOI: 10.1039/D0NJ01343A
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A Novel AIE Chemosensor Based on Coumarin Functionalized Pillar[5]arene
for Multi-analytes Detection and Application in Logic Gate
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
a
a
a
Hong-Qiang Dong , Xiao-Qiang Ma, Tai-Bao Wei,* Qing-Yu Yang , Yun-Fei Zhang , Qin-Peng
a
a
a b
a
Zhang, Hong Yao You-Ming Zhang , and Qi Lin*
DOI: 10.1039/x0xx00000x
Aggregation induced emission (AIE) active molecules are widely applied for multi-analytes detection due to their unique
advantages over conventional fluorescent probes. Herein, a novel coumarin functionalized pillar[5]arene (PX) has been
designed and synthesized. It has the strong AIE activity, the fluorescence quantum yield of PX turned out to be 35.0% in
DMF/H
2
O (7:3, v/v) binary solution (1.0 × 10-4 M). Meanwhile, the optimized structure of PX was obtaied by theroretical
calculation at the B3LYP/6-311G leve. Interestingly, the PX displays high sensitivity to multi-analytes, such as Fe3+ and Ba2+.
The limits of detections (LODs) of PX for Fe3+ and Ba2+ are 1.67×10-7 M and 5.89×10-8 M, respectively. In addition, by
introducing metal ions into the AIE chemsensors of PX, metal-coordinated chemosensor(PX-M) was obtained, The PX-Fe
-
-7
-
-7
and PX-Ba shows selective fluorescence “turn on” detection of H
2 4
PO (LODs = 1.50×10 M) and CN (LODs = 6.20×10 M),
respectively. The multi-analytes detection mechanism of PX was based on multiple competitions of “exo-wall π-π”
3
+
2+
-
-
2 4
interactions and cation-π. Notably, we have prepared logic gates controlled by Fe /Ba and H PO /CN at the molecular
level, which can quickly and efficiently detect ions in aqueous solutions. Moreover, we also prepared test films, the Fe3+ test
kit was prepared by loading PX on a silica gel plate. This study provides a new way for multi-analytes detection.
AIE feature have attracted great attention in various fields
Introduction
[20-22]
because of their unique properties.
So far, people have
obtained various AIE compounds. In addition, recent studies
have found that as a new generation of macrocyclic
compounds, pillar[n]arene also have the AIE phenomenon and
can be used as new AIEgen. However, little has been reported
about the AIE aspects. Therefore, designing and synthesizing a
The recognition and quantitation of metal ions are of great
importance in chemical, biological, and environmental fields.
For example, iron is an essential trace element in the human
body, it is involved in the delivery of oxygen with the
[
1,2]
[
3]
combination of haemoglobin. Nevertheless, excessive intake
of Fe3+ can cause serious physiological diseases, like liver and
[23-26]
novel AIE macrocycles groups is still a charming challenge.
[
4]
2+
kidney damages. Meanwhile, the superfluous Ba could also
cause corresponding effects and life-threatening. [5,6] In addition,
Pillar[n]arene as a new generation macrocyclic molecule, after
[
27]
crown ethers, cyclodextrins, cucurbiturils and calixarenes,
cyanide as one of the highest toxic compounds was widely
[
28]
[
7-9]
was first reported by Ogoshi et al in 2008. It is widely used in
found in amygdalin and other natural products.
The
[
29,30]
[31]
cell imaging, [32] ion detection,
-
catalysis,
drug release,
sensitive and selective detection of cyanide (CN ) in water or
[
33-35]
due to the rich π-electron system, hydrophobicity and easy
water-containing systems has been still a puzzle for scientists all
modification. [27] In addition, pillar[n]arenes could complex with
different guest via various weak interactions, such as hydrogen
around the world. [
10-12]
Therefore, it is necessary to develop a
novel chemosensor for detecting metal ions and high toxic ions
in highly sensitivity.
bonding, [ π-π stacking,
cation-π
36]
[37,38]
electrostatic interaction,
[39,40]
[
41,42]
[43,44]
and “exo-wall” π-π interactions.
This
[
45]
[
13,14]
provides a good opportunity for multi-analytes detection.
Moreover, Coumarin is greatly abundant in nature, which has
Since AIE was reported by Tang. et al. in 2001,
it has been
[
15]
chemical sensing, [16] explosives
detection [ and organic light-emitting diodes (OLED) etc.
widely used in bioimaging,
[
46,47]
17]
[18,19] potential medical value and good fluorescent group.
From
the viewpoint of molecular engineering, the structure of
In the past decade，organic luminescent chemosensors with
coumarin is a two-ring system, which provides a good π-system
for the research system. [
48-50]
However, there are few reports
a. Key laboratory of Polymer Materials of Gansu Province, College of Chemistry and
Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P.
R. China. E-mail: weitaibao@126.com. linqi2004@126.com.
Deputy Director-General of Gansu Natural Energy Research Institute, Renmin
Road 23, Lanzhou, Gansu, 730070, P. R. China.
Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
on the performance of coumarin AIEgens. In addition, the
coumarin platform has been widely adopted in the design of
small-molecule fluorescent chemosensors because of its strong
b.
[
51-
and stable fluorescence emission, and good rigid structural.
†
5
3]
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In the view of this and background of our research group. [54,55] Synthetic procedures
We reported a novel coumarin functionalized pillar[5]arene, PX
exhibited strong blue fluorescence in DMF/H
solution and fluorescence quantum yield was reach 35.0%. It
can be quenched by the addition of Fe and Ba , Their
detection limits are 1.67×10 M and 5.89×10 M, respectively.
Meanwhile, PX could also alternately detect H
detection limits of PX toward H
and 6.20×10-7 M, respectively. Additionally, the results
mentioned above also clarify our point of view through density
functional theory. The logic gate was successfully constructed
based on the alternant detection property of PX.
Simultaneously, for practical applications of chemosensor PX,
View Article Online
DOI: 10.1039/D0NJ01343A
Br
2
O (7:3, v/v) binary
O
O
O
O
O
2
KI, K2CO3
3
+
2+
+
Acetone refulx 3 day
(CH O)n
BF3·Et2O
-7
-8
OH
1,2-dichloroethane
3
0℃,30min
-
-
Br
2
PO
4
and CN , the
-
-
-7
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2
PO
4
and CN were 1.50×10 M
Br
O
O
O
Br
O
HO
O
O
O
O
O
O
DMF/Acetone (3:50, v/v)
KI, K2CO3
O
3
+
O
test strips were prepared and utilized to sense Fe .
O
O
O
O
O
O
O
6
5 ℃ reflux 3 day
O
O
Experimental
Materials and methods
O
O
O
O
1
PX
Varian Mercury 400 and Varian Inova 600 instruments were
Scheme 1. Synthetic route to compound PX
1
13
used for obtaining H NMR and C NMR spectra. MS spectra
were recorded with a Bruker Esquire 6000 MS instrument.
Fluorescence spectra were recorded using shimadzu RF-5301PC
spectrophotometer. Digilab FTS-3000 FTIR spectrophotometer
were used for obtaining IR spectra. By FE-SEM (JSM-6701F,
accelerating voltage of 5 kV) characterized morphologies of
solid compound. Single crystal X-ray diffraction data was
collected on a transmission mode with a Rigaku RINT2000
diffractometer equipped, using graphite monochromated CuKa
Synthesis of PX: Pillar[5]arene 1 (0.9 g, 1 mmol) and 7-
hydroxycoumarin (0.2 g, 1.2 mmol) were added to a solution of
KI (0.498 g, 3 mmol) and K CO (0.828 g, 6 mmol) in N,N-
2 3
Dimethylformamide/acetone (3:50, v/v). The mixture was
heated under nitrogen atmosphere and refluxed for 3 day, As
shown in Scheme 1. After the reaction is completed, it is washed
with sodium hydroxide solution to remove excess 7-
hydroxycoumarin. The crude product was isolated by column
chromatography using petroleum ether/ethyl acetate (20:1,
(λ = 1.54073 Å) radiation. Gaussian 09 code was employed for
[
56]
all quantum chemistry calculations. all analyses as well as
drawing of various kinds of maps were finished via the
Multiwfn3.7(dev) code.[
spectra of the synthesized compound were recorded on
addition of perchlorate salts while keeping the ligand
concentration constant (1.0 × 10 M) in all experiments. Metal
ions had been used as perchlorate salts and anions had been
used as tetrabutylammonium salts, which were prepared with
1
v/v) to get a white solid PX (0.72 g, 80%).M.P. 113-115 °C. H
57]
NMR(Fig. S2) (600 MHz, CDCl
3
, room temperature) δ (ppm):
.97 (d, J =14.4Hz, 1H), 7.59 (d, J =10.2 Hz, 1H), 6.91 (d, J=15 Hz,
H), 6.76 (m, 10H), 6.27 (d, J =14.4 Hz, 1H), 4.02 (t, J =9.6 Hz,
4H), 3.64 (s, 37H), 1.72 (m, 4H), 1.47 (m, 4H). C NMR (Fig. S3)
150 MHz, CDCl ,room temperature) δ (ppm): 160.8, 159.0,
56.5, 147.4, 143.5, 129.4, 113.8, 111.1, 104.1, 68.7, 56.1, 30.1,
Any changes in the fluorescence
7
2
1
3
-4
(
1
2
3
+
64
5.9. ESI-MS m/z: [PX+H] Calcd C59H O13 980.44, found 981.44
0
.1 M throughout all fluorescence experiments.
(
Fig.S4).
Fig. 1 (a) Fluorescence intensity of PX in DMF/H
2
O binary solution with different water fraction, solution
concentration: 1.0 × 10 M; (b) The Tyndall effect of PX (1.0 × 10-4 M) with different volumetric fractions of water
Vol%).
-4
(
2
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Results and discussion
AIE experiment
confirmed the presence of “exo-wall” π-π stacking interactions
View Article Online
through X-ray diffraction peaks at 2 = D2O2I.:4130.1 and 30.10
039/D0NJ01343A
。 。
corresponding to d-spacings of 3.97Å and 3.86Å (Fig S8).
We have rationally linked the pillar[5]arene with 7-
hydroxycoumarin by etherification reaction to construct a novel
coumarin functionalized pillar[5]arene AIE chemosensor (PX)
We further performed Density Functional Theory (DFT)
calculations using Gaussian 09 on our system to elucidate the
reasons for the observed discriminative fluorescence sensing.
1
13
(Scheme 1). The PX was characterized by H NMR and CNMR,
and ESI mass spectra (Fig. S1-S4). First, we found that the novel [56-59]
AIE chemosensor PX has weak fluorescence in pure DMF
One monomer unit of PX as a representative fragment was
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considered as the energy-minimized structure. We also
modelled the VOC considered in this study. Geometry
optimization was done using DFT by employing the hybrid
B3LYP / 6-311G level. The energy-minimized structures of PX
were obtained (Fig. 3-a). We found that the oxygen atom on the
unsaturated keto ester group exhibited strong electronegativity
solution. However, the fluorescence of PX could be enhanced
by adding water ， when the water content is 30%, the
fluorescence emission is the largest (Fig. 1-a). the PX exhibited
strong fluorescence which could be attributed to the
accumulation of PX. The optical measurements of PX were
conducted in DMF/H
2
O (7:3, v/v) binary solution at a fixed
(
Fig. 3-b), while the pillar[5]arene hydrocarbon benzene ring
concentration (1.0 × 10− M). Next, from the Commission
Internationale de L'Eclairage (CIE) photograph, it can be seen
that the novel AIE chemosensor has blue fluorescence (Fig. S5).
Meanwhile, Tyndall effect could also be observed in 30%
aqueous system (Fig. 1-b). In addition, we calculate the
fluorescence quantum yield of 35.0%, according to the
corresponding formula, using quinine sulfate as standard (Fig.
S6).[ To this end, we did a series of experiments on the
mechanism explanation of AIE.
4
and methoxy group exhibited positive dielectric properties, and
we calculate the HOMO and LUMO orbital distribution
according to the frontier orbital theory by calculating the
frontier orbit of PX. From Fig. S9, we can see that the HOMO
orbit is distributed on the pillar[5]arene, and the LUMO orbit is
distributed on the coumarin. This indicates that the site of
action is between the column aromatics and coumarin, which
further proves the existence of the “exo-wall” π-π. In addition,
a vigilant inspection of the graphical representation of NCI-RDG
isosurfaces for the complexes portrayed in Fig. S10 suggests
60]
AIE mechanism explanation
First of all, in order to further study the AIE property of PX, we plethora of interactions indicated with green isosurfaces
1
verified it by H NMR titration methods, 2D NOESY NMR, X-RD, extending over in the attractive low-density low-gradient region
1
SEM, etc. In the H NMR titration (Fig. 2) of PX, with the addition These results indicated that the fluorescence of PX in DMF/H
2
O
of D
showed distinct downfield shift and the protons peaks of H
and H upfield shifts. we speculated that it may have formed
exo-wall” π-π interaction between PX molecules. Meanwhile,
2 c b
O, the protons peaks of H and H on pillar[5]arene group binary solution is AIE. By the above results, we propose the self-
a 1
, H ,
assembly mechanism of PX (Scheme 2b).
H
2
3
“
we validated the “exo-wall” π-π interaction mechanism via 2D
NOESY NMR. As shown in Fig. S7, there are no correlations
between the signals of protons H , H , H and H , H , H , which
a b c 1 2 3
implied that coumarin was not threaded into the cavity of
pillar[5]arene. These results revealed that the PX could self-
assemble via “exo-wall” π-π interactions. Furthermore, we also
Fig. 3 (a)The optimal structure of a bilayer PX; (b) Electronic
potential maps (ESP, in atomic units) of PX at the B3LYP/6-311G
level.
1
Fig. 2 Partial H NMR titration spectra of PX (10mg/ml) in
DMSO-d6 solution with different amount of D O (a) 0%; (b)
2
5%; (c) 10%; (d) 20%;(e) 30%;(f) 40%.
This journal is © The Royal Society of Chemistry 20xx
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DOI: 10.1039/D0NJ01343A
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Scheme 2. (a) Chemical structures of PX; (b) Illustration of the formation of dimer structure
with PX;(c) Cartoon representation for the formation of the “exo-wall π-π”; (d) Cartoon
representation for the formation of new type of assembly PX-M.
-7
Ion detection
the detection limit is 1.50×10 M (Fig. S15). Through the same
experiment, we found that PX-Ba fluorescence recovered
when 5.33 equiv. CN was added (Fig. 5-d). And the detection
2
+
Cation detection
-
Due to the hydrophobic effect of the Pillar[5]arene cavity, limit is 6.20×10-7 M (Fig. S16). Finally, we implemented anti-
Pillar[5]arene insoluble in water solutions. Therefore, we chose interference experiments separately (Fig. S17-18), and found
2
DMF/H O binary solution for the fluorescence studies. The that they have right selective recognition.
fluorescence behavior of PX towards metal ions was carried out
in DMF/H
carefully investigated the selectivity of AIE chemosensor PX in
-4
2
O (7:3, v/v) binary solution (1.0 × 10 M). First, we
We believe that this “on-off-on” phenomenon of fluorescence is
2
+
2+
2+
the presence of various metal ions (including Zn , Pb , Cd ,
3
+
2+
2+
+
2+
2+
3+
2+
3+
3+
3+
Fe , Co , Hg , Ag , Ca , Mg , Cr , Ba , Eu , La and Al ).
Fig. 4). After 2.0 equiv. of various cations were added into PX
(
3
+
2+
solutions, we found that only Fe and Ba could quench the
fluorescence, that indicated PX could achieve the fluorescent
detection of Fe3+ and Ba . Next, we investigated the AIE
2+
3
+
2
chemosensor PX in the DMF/H O (7:3, v/v) with the Fe and
2
+
Ba . We found that it is consistent with the above
phenomenon, which indicates that the sensor PX has superior
3
+
2+
recognition characteristics for Fe and Ba . When 2.53 equiv.
3
+
Fe is added, the end of the titration is reached, we can see that
the peak at 385nm is significantly reduced, the detection limit
[
61]
-7
was calculated on the basis of 3σ/S, which is 1.67×10 M (Fig.
S11). Similarly, For Ba (Fig. 5-b), The end point of the
fluorescence titration reached when 2.67 equiv. were added,
the detection limit of the fluorescent spectra is 5.89×10 M (Fig.
S12).
2
+
-8
Anion detection
Fig. 4 Fluorescence emission (λex = 320 nm) spectra of PX
-
4
2+
2+
2+
3+
2+
(
1.0×10 M) with metal ions (Zn , Pb , Cd , Fe , Co ,
In order to further evaluate the host stimuli-response
2
+
+
2+
2+
2+
3+
3+
3+
3+
3
+
2+
-
-
Hg , Ag , Ca , Mg , Ba , Cr , Eu , La and Al ) in the
DMF/H O (7:3, v/v) binary solution in response to Fe and
2
properties of PX-Fe / Ba , we added different anions (F , Cl ,
3
+
-
-
-
-
-
-
-
-
-
-
2-
Br , I , AcO , HSO
4
, H
2
PO
4
, ClO
4
, CN , SCN , N
3
, OH and S ).
2
+
3
+
-
Ba (2.0 equiv.).
Interestingly, for PX-Fe , when adding H
shows up (Fig. S13), At the same time, for PX-Ba , the
fluorescence appears to be open when CN is added (Fig. S14).
Then, we performed a fluorescence titration experiment, when
2
PO
4
, the fluorescence
2
+
firstly caused by the addition of water, which leads to the self-
assembly of PX through the “exo-wall” π-π interactions,
producing AIE and enhancing the fluorescence. Later, when the
iron or barium ions were added, this assembly was destroyed and
-
-
5
.67 equiv. H
2
PO
4
was added, the fluorescence recovered and
at 385 nm, the emission peak appeared (Fig. 5-c)., moreover,
4
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6
2
+
Ba from the SEM (Fig. 6-c). After the ions form a very regular
View Article Online
DOI: 10.1039/D0NJ01343A
block compound, which indirectly proves our theory above; when
-
the CN is added, the complexation occurs, the system restores
the “exo-wall π-π”, the fluorescence is turned on (Scheme 2), and
-
we can also get from the SEM. It is seen that the addition of CN
-
and H
2
PO
4
forms a coral-like shape (Fig. 6-d and Fig.S20).
Meanwhile, In the IR spectra of PX, the -CH=CH- (coumarin)
-
1
vibration absorption peak of appeared at 2942 cm . With the
0
1
2
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8
9
0
1
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3
+
2+
3+
addition of Fe /Ba into PX and the formation of PX-Fe /PX-
2
+
-1
Ba , the -CH=CH- vibration absorption peak shifted to 2937 cm ,
3
+
2+
indicating that the PX combined with Fe /Ba via cation-π
-
-
2 4
interactions. As expected, after the addition of H PO /CN into
3
+
2+
the PX-Fe /PX-Ba , the -CH=CH- vibration absorption peak
recovered to the initial position (Fig. S21-S22). Meanwhile, the
XRD pattern of the PX-M (M: Fe , Ba ) showed peaks
3
+
2+
-
-
2 4
disappeared, Interestingly, after adding H PO and CN to the PX-
Fig. 5 Emission spectra of (a) PX with increasing amounts of
3
+
2+
。
。
3+
2+
3+
M (M: Fe , Ba ), the strong peak at 2 = 22.92 and 2 = 22.76
Fe ;(b) PX with increasing amounts of Ba ; (c) PX-Fe with
-
/CN-
-
2+
appeared again (Fig. S23), which confirmed that H
2
PO
4
increasing amounts of H
amounts of CN . (solution concentration:1.0×10 M, λex = 320
nm, λem = 385 nm)
2
PO
4
; (d) PX-Ba with increasing
3
+
2+
-
-4
competitively bound with Fe /Ba and the PX recovered.
Moreover, we made the working curves and ESI-MS of
PX+Fe /Ba , respectively, and found that they are all 1:1
3
+
2+
a new assembly was formed, resulting in fluorescence quenching. coordination (Fig. S24-S27). In addition, we synthesized Control
Meanwhile, with the addition of anions, they interact with Compound 2 and conducted a control experiment (Fig. S28-S29).
cations, so the system restored and fluorescence recovery.
When water was added to compound 2, compound 2 did not
undergo significant aggregation-induced emission (Fig. S30a).
Therefore, the introduction of pillar[5]arene can be effectively
3
+
2+
Next, the stimulus-response mechanism of PX-M (M: Fe , Ba ) used as AIEgens, so that PX exhibits good aggregation-induced
was carefully investigated via NMR, SEM and IR analysis. In the H emission. At the same time, the addition of Fe3+/Ba2+ to the DMF:
NMR titration spectra(Fig. S19), we gradually added Ba2 and H2O (7:3, v/v) binary solution of compound 2 did not cause a
found that the H
while the hydrogen in the pillar[5]arene H
the long alkyl chain did not shift, but the protons peak of H
the methoxy group shows downfield shifts. Therefore, we deduct
the formation of the cation-π effect and form a new assembly
method. At the same time, we can also see the addition of PX-
1
+
1
, H , H
3 4
on the coumarin to the upfield shifts, significant decrease in fluorescence (Fig. S30b), which also proves
of benzene ring and that PX achieves multi-analytes detection through the “exo-wall”
on π-π interactions and cation-π interactions.
c
b
Based on the reversibility of the PX switchable state between
different fluorescent emissions, named ON (fluorescence
emission) and OFF (fluorescence quenching). To this end, we
have designed a logic gate operation based on the molecular
level, which shows the cyclic behaviour of "reading, erasing,
3
+
2+
reading, writing" (Fig. 7). For input, the addition of Fe /Ba is
-
-
2 4
defined as “1”, and the absence of H PO / CN is defined as “0”,
Fig. 7 (a) The truth table. (b) Feedback loop showing the
reversible logic operations for the memory element with
2
+
2
Fig. 6 SEM images of (a) PX; (b) PX-H O; (c) PX-Ba ; (d)
2
+
-
PX-Ba +CN .
‘
‘Writing–Reading–Erasing–Reading’’ functions.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
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for output, we defined the normalized fluorescence intensity of
PX turn on as “1” and turn off as “0”. From the truth table (Fig.
Notes and references
View Article Online
DOI: 10.1039/D0NJ01343A
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-a), it could be observed that the presence of only Fe /Ba
Chem., 2018, 110, 303-320.
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emission implying that the output signal was above the
threshold value (output = 0). However, other possible input
combinations [(0, 0), (0, 1), and (1, 1)] could lead to the output
signal below the threshold value, i.e. the output = 1. Therefore,
an IMPLICATION logic gate was successfully constructed by
monitoring the fluorescent change of chemosensor PX at 385
0
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3
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9
0
1
2
3
4
5
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7
8
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0
3
+
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-
-
2 4
nm with the two inputs (Fe /Ba and H PO /CN ).
1
12.
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In order to further develop the practical application value of the
chemosensor PX, we prepared a corresponding film, immersed
a silica gel plate in a binary solution containing PX, and dried it
in the air to obtain a film (Fig. S31). Under the irradiation of an
ultraviolet lamp(365nm), the film showed very strong blue
fluorescence, immersing the film in an aqueous solution
8
9
1
3
+
-7
containing different concentration Fe (from 1.0 M to 1×10
11 S. Wang, W. Gao, X. Y. Hu, Y. Z. Shen, L. Y. Wang, Chem.
Commun , 2019, 55, 4137-4149.
2
+
-8
-
(from 1.0 M to 1×10-
M), Ba (from 1.0 M to 1×10 M), H
2
-7
PO
4
.
7
-
M) and CN (from 1.0 M to 1×10 M). we can see different 12 B. R. Yong, T. B. Wei, W. J. Qu, Q. Lin, Y. M. Zhang, H. Yao. H
New J. Chem., 2018, 42, 14766-14771.
fluorescence performance under UV light. Therefore, based on
1
3 F. N. Moghadam, M. Amirnasr, K. Eskandari, S. Meghdadi,
3
+
the PX-supported silicone film, it can efficiently detect Fe
,
New J. Chem., 2019,43, 13536-13544.
2
+
-
-
2 4
Ba , H PO , CN and security materials.
14 J. D. Luo, Z. L. Xie, J. Lam, L. Cheng, H. Y. Chen, C. F. Q. Kwok,
X. W. Zhan, Y. Y. Liu, D. B. Zhu and B. Z. Tang.
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2
019, 62, 1090-1098.
We designed and synthesized a novel coumarin functionalized
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exhibiting multiple stimulating properties for Fe and Ba by
0
0, 1-3.
-
forming a cation-π effect, and their detection limits are 1.67×10
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7
-8
M and 5.89×10 M, respectively. Simultaneously, through the
16445-16453.
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+
20 R. Hu, A. J. Qin, B. Z. Tang, Prog.ꢀPolym.ꢀSci., 2020, 100,
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-
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101176.
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2
1 R. R. Hu, N. L. C. Leung, B. Z. Tang, Chem.ꢀSoc.ꢀRev., 2014, 43,
-
7
-7
detection limits are 1.50×10 M and 6.20×10 M, respectively.
In addition, other anions have little effect on their interference.
The PX could be act as AIE chemosensor for detection of multi-
analytes. In summary, this study not only supplies an efficient
route to response to multi-analytes but also provides a new
approach for constructed of pillar[5]arene-based AIE
chemosensor.
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Conflicts of interest
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This work was supported by the National Natural Science
Foundation of China (No. 21662031; 21661028; 21574104) and
the Program for Chang jiang Scholars and Innovative Research
Team in University of Ministry of Education of China (No. IRT
0 A. A. Nazarova, L. S. Yakimova, P. L. Padnya, V. G.
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View Article Online
DOI: 10.1039/D0NJ01343A
A Novel AIE Chemosensor Based on Coumarin Functionalized
Pillar[5]arene for Multi-analytes Detection and Application in
Logic Gate
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Hong-Qiang Dong , Xiao-Qiang Ma , Tai-Bao Wei *, Qing-Yu Yang , Yun-Fei
Zhang , Qin-Peng Zhang , Hong Yao , You-Ming Zhang and Qi Lin a*
a
a
a
a, b
Graphical Abstract
A novel coumarin functionalized pillar[5]arene (PX) with AIE fluorescence could
sequentially detection of multi-analytes aqueous medium with high sensitivity.