A novel AIE chemosensor based on quinoline functionalized Pillar[5]arene for highly selective and sensitive sequential detection of toxic Hg2+ and CN?

Article abstract of DOI:10.1016/j.dyepig.2019.01.049

Aggregation-induced emission (AIE) is widely used for fluorescence “on-off-on” detection ions and molecular. Herein, we report a novel AIE chemosensor through self-assembly of quinoline functionalized pillar[5]arene (SPQ5). The SPQ5 can bind with Hg²

Full text of DOI:10.1016/j.dyepig.2019.01.049

Accepted Manuscript
A novel AIE chemosensor based on quinoline functionalized Pillar[5]arene for highly
2+
−
selective and sensitive sequential detection of toxic Hg and CN
Xiao-Qiang Ma, Yun Wang, Tai-Bao Wei, Li-Hua Qi, Xiao-Mei Jiang, Jin-Dong Ding,
Wen-Bo Zhu, Hong Yao, You-Ming Zhang, Qi Lin
PII:
S0143-7208(19)30010-5
https://doi.org/10.1016/j.dyepig.2019.01.049
DYPI 7322
DOI:
Reference:
To appear in: Dyes and Pigments
Received Date: 3 January 2019
Revised Date: 28 January 2019
Accepted Date: 28 January 2019
Please cite this article as: Ma X-Q, Wang Y, Wei T-B, Qi L-H, Jiang X-M, Ding J-D, Zhu W-B, Yao H,
Zhang Y-M, Lin Q, A novel AIE chemosensor based on quinoline functionalized Pillar[5]arene for highly
2+
−
selective and sensitive sequential detection of toxic Hg and CN , Dyes and Pigments (2019), doi:
https://doi.org/10.1016/j.dyepig.2019.01.049.
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ACCEPTED MANUSCRIPT
Graphical Abstract
a
a
a
a
a
Xiao-Qiang Ma , Yun Wang , Tai-Bao Wei *, Li-Hua Qi , Xiao-Mei Jiang , Jin-Dong
a
a
a
a,b
a
Ding , Wen-Bo Zhu , Hong Yao , You-Ming Zhang and Qi Lin *
A novel 8-hydroxyquinoline functionalized pillar[5]arene (SPQ5) with AIE
2
+
-
fluorescence could sequentially detect toxic Hg and CN in aqueous medium with
high selectivity and sensitivity
.

ACCEPTED MANUSCRIPT
A Novel AIE Chemosensor Based On Quinoline Functionalized
Pillar[5]arene for Highly Selective and Sensitive Sequential
2
+
-
Detection of Toxic Hg and CN
a
a
a
a
a
Xiao-Qiang Ma , Yun Wang , Tai-Bao Wei *, Li-Hua Qi , Xiao-Mei Jiang , Jin-Dong
a
a
a
a, b
a
Ding , Wen-Bo Zhu , Hong Yao , You-Ming Zhang and Qi Lin *
a
Key laboratory of Polymer Materials of Gansu Province, College of Chemistry and
Chemical Engineering, Northwest Normal University, Lanzhou 730070, China.
E-mail: weitaibao@126.com, linqi2004@126.com
b
College of Chemistry and Chemical Engineering, Lanzhou City University, Lanzhou,
Gansu, 730070, China.
ABSTRACT
Aggregation-induced emission (AIE) is widely used for fluorescence “on-off-on”
detection ions and molecular. Herein, we report a novel AIE chemosensor through
self-assembly of quinoline functionalized pillar[5]arene (SPQ5). The SPQ5 can bind
2
+
2+
with Hg tightly through coordinating reaction. By introducing Hg into AIE-based
2
+
chemosensor, metal-coordinated chemosensor (SPQ5-Hg ) was obtained, the
2
+
-
SPQ5-Hg could high selectively and sensitively detection of CN by competitive
2
+
-
-8
coordinating interactions. The LODs of SPQ5 for Hg and CN are 2.53×10 M and
-8
2+
7
.71×10 M, respectively. In addition, Hg test kit was prepared by loading the
SPQ5 chemosensor on a silica gel plate, which could more convenient and efficiency
2
+
-
detection Hg and CN . Interestingly, the chemosensor SPQ5 could instant sense the
2
+
-
Hg and CN by the changing of fluorescence color and fluorescence intensity.
2
+
Notably, the fluorescence intensity changes of SPQ5 upon the addition of Hg and
-
2+
-
CN were utilized as an IMP logic gate at the molecular level, using Hg and CN as
chemical inputs and the fluorescence intensity signal as the output. On the other hand,

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the test kit by loading SPQ5 on a silica gel plate was prepared for convenient
2
+
detection of Hg . This study provides a practical application for the sensing of toxic
ions in aqueous solution by the construction of supramolecular system.
Keywords: Toxic ion; AIE fluorescence; Pillar[5]arene; Chemosensor; Highly sensitive
detection; Logic gate.

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1
. Introduction
In recent years, detection of toxic ions has gained paramount importance in
biological, chemical and environmental applications. Among the various cations and
anions, mercury and cyanide are considered to be toxic ions for human health and
natural environment. Mercury is one of the well-known heavy toxic metal which can
exist in different forms, such as elemental, organic and inorganic forms [1-2]. The risk
of such pollutants even at invisible trace level is that they can be progressively
concentrated through the food chain and form a threat to human health. Moreover,
low concentration of mercury induces wide variety of serious health effects. Similarly,
-
-
CN is considered as one of the most toxic anions due to CN could associated with
binding to the iron in hemoglobin, which interrupts electron transport and causes
-
hypoxia [3-4]. In spite of its extreme toxicity, the CN is still extensively used in the
gold and silver mining industry, plastic manufacturing and resin industry. Therefore,
the quantitative detection of toxic ions are important area of ions detection research.
Chemosensors for sequential detection of diverse cations and anions, such as
anion-anion [5-6], anion-cation [7-8], cation-anion [9-11], cation-cation [12-13], has
been reported. An example of the sequential detection toxic ions via a single
fluorescent chemosensor has been little reported to date. Additionally, development of
selective and sensitive probes with environmental interest for the determination and
visualization of analytes (metal ions [14-16], anions [17-19] and molecular [20-22]) is
a very attractive research topic in the chemosensors [23-24]. A various of analytical
2
+
-
methods has been reported [25-29] for detection of Hg and CN , but the

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fluorescence based technique is always attractive because of their high sensitivity,
sensitive response time, and simple technology. The 8-hydroxyquinoline moiety has
valuable structural characteristics of the most widely employed molecular platforms
to construct many unique ionophoric systems for the recognition of important metal
ions and effective light-emitting devices [30-31]. In recently, quinoline-functionalized
pillar[5]arene reported by others mainly was supplied in fields of detection for
radioactive element [32] and gas adsorption [33]. However, 8-hydroxyquinoline
functionalized pillar[5]arene with AIE for detection of toxic ions is rarely.
Aggregation-induced emission (AIE) is a fluorescent phenomenon that a molecule
or molecular fragment exhibits enhanced fluorescence properties in the aggregated
state, as results of restriction of intramolecular motions, rotations or vibrations, that
leaded to the three-dimensional (3D) conformations of AIE gens effectively
strengthened aggregated-state fluorescence [34-35]. Fluorescence based on AIE
chemosensors have emerged to show great potential for chemical sensing [36-38],
optoelectronic applications [39-41] and bio-imaging [42-44]. Construction of
functional supramolecular polymer into AIE molecule can greatly expand their
potential fluorescence sensing application [45-48]. In recent years, tetraphenylethene
(
TPE) has been vibrantly developed, due to TPE containing four rotatable phenyl
rings exhibits AIE activity [49-51]. Additionally, triphenylamine [52-53] and 1,
-Naphthalimide [54-56] derivatives are also receiving continuous attention owing to
8
their wide AIE activity in ions detection and biological images.
Pillar[n]arenes as a new class of macrocyclic host have been widely reported due to
their intrinsic uniquely rigid symmetrical pillar architecture and easy function

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properties [57-59]. Pillar[5]arene-based various self-assembly driving forces such as
hydrogen bonds [60-61], π-π stacking [62-63], host-guest interactions [64-65] and
metal-ligand binding [66-67] C-H···π interactions [68-69] and so on. Much more
importantly, these various self-assembly driving forces also provide good
opportunities to achieve controllable multi-stimuli response [70-71]. Developing a
pillar[5]arene chemosensors based on AIE activity are always an important topic in
this area. Therefore, they have obtained more and more attention of researchers in
recent years. In our recent research, we found that pillar[5]arene-based
supramolecular also reveal AIE activity [72-73].
In view of these and as a part of our research interests in ions recognition and
pillar[5]arene-based supramolecular chemosensors [74-78], we report a novel
8
-hydroxyquinoline functionalized pillar[5]arene fluorescent probe (SPQ5), which
shown strong AIE fluorescence in aqueous solution. The SPQ5 could act as an
2
+
AIE-based chemosensor for highly selectivity and sensitivity detection of Hg and
-
CN in DMF/water (8:2, v/v) binary solution by coordination interaction. The LODs
2
+
-8
-
-8
of SPQ5 for Hg is 2.53×10 M and CN is 7.71×10 M, respectively. Moreover,
2
+
other cations and anions didn’t interfere in the sensing processes. The Hg sensing
2
+
mechanism was based on coordination between Hg and SPQ5, fluorescence recover
-
-
2+
by added CN due to CN break this coordination. In addition, Hg test kits, prepared
by loading the SPQ5 on silica gel plates, could conveniently and efficiently detection
2
+
of Hg in aqueous solution with highly sensitivity. Meanwhile, we design IMP logic
2
+
-
gate controlled by Hg and CN can provide significantly increased the ability to
expand the repertoire of available operations.

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2
. Experiment
2
.1. Materials
Unless otherwise stated, all chemical reagents were obtained from commercial
suppliers and used without further purification. Solvents used were purified and dried
by standard methods prior to use. Commercially and were used without further
purification. All the anions were added in the form of tetra butyl ammonium (TBA)
salts, which were purchased from Sigmae Aldrich Chemical, stored in a vacuum
desiccator. All cations were used as the perchlorate salts, which were purchased from
Alfa Aesar and used as received.
Scheme 1
2
.2. Instruments
Melting points were measured on an X-4 digital melting point apparatus and were
uncorrected. Fluorescence spectra data were recorded on Shimadzu RF-5310
spectrometer. The NMR spectra were obtained on a Mercury-600 BB spectrometer
with tetramethylsilane (TMS, δ scale with solvent resonances as internal standards) as
inner standard. High-resolution MS was conducted on a Bruker Esquire 3000 Plus
spectrometer (Bruker-Franzen Analytik GmbH Bremen, Germany) equipped with ESI
interface and ion trap analyzer. Powder X-ray diffraction data were collected using a
Rigaku RINT2000 diffract meter equipped (copper target; λ = 0.154073 nm).
Scanning electron microscopy (SEM) images of the xerogels were investigated using
JSM-6701F instrument.
2
.2. Synthesis of SPQ5
Synthesis of SPQ5: Pillar[5]arene 2 (0.9 g, 1 mmol) and KI (0.183 g, 1.1 mmol)
were added to a solution of K CO (0.138 g, 1 mmol) and 8-hydroxyquinoline(0.16 g,
2
3
1
.1 mmol) in acetone/N,N-Dimethylformamide (v/v 50:3). The mixture was heated
under nitrogen atmosphere at reflux for 48 h. As shown in Scheme 2. The solid was
filtered off and the solvent was removed. The crude product was isolated by column

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chromatography using petroleum ether/ethyl acetate (v/v 5:1) to get a white solid
1
SPQ5 (0.61 g, 63%). m.p. 92-94℃ . H NMR (Fig. S3) (600 MHz, CDCl , room
3
temperature) δ (ppm): 8.95 (d, J=4Hz, 1H), 8.12 (t, J=8Hz, 1H), 7.45 (m, 2H), 7.38 (d,
J=8Hz, 1H), 7.07 (d, J=6Hz, 1H), 6.78(m, 10H), 4.27 (d, J=8.3Hz, 2H), 3.86 (t,
J=6Hz, 2H), 3.76 (d, J=10.5Hz, 10H), 3.66 (m, 27H), 2.10 (m, 2H), 1.86 (t, 2H), 1.64
1
3
(
t, J=7.2Hz, 4H). C NMR (Fig. S4) (150MHz, CDCl , room temperature) δ (ppm):
3
1
1
3
55.04, 150.88, 150.84, 150.20, 149.54, 140.64, 136.11, 129.74, 128.57, 128.44,
28.36, 126.89, 121.76, 119.69, 115.01, 114.11, 140.01, 108.84, 69.03, 68.57, 55.91,
+
0.07, 29.55, 26.31. ESI-MS m/z: [SPQ5] Calcd C H N O 964.17, found 964.46.
59
65
1
11
(Fig. S5).

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. Results and discussion
3
A novel quinoline functionalized pillar[5]arene derivative (SPQ5) has been
synthesized by rationally connected pillar[5]arene moiety and an
-hydroxyquinoline groups (Scheme 1). SPQ5 and its intermediate were characterized
a
8
1
13
by H NMR and C NMR, and ESI mass spectra (Fig. S1-S5). Interestingly, the
SPQ5 as novel AIE active moiety caused by pillar[5]arene shows strongly AIE
fluorescence. In order to investigate the AIE influence, a series of aggregated
fluorescence experiment were carried out (Fig. 1). The optical measurements of SPQ5
were conducted in DMF/H O (8:2, v/v)binary solution at a fixed concentration
2
-4
(
2.0×10 M). The supramolecular chemosensor SPQ5 has almost no fluorescence in
pure DMF solution (Fig. 1). Upon the addition of various water content, the SPQ5
exhibits enhanced aggregation fluorescence as water content increases and reaches the
strongest emission intensity at f = 20%, with the relative emission intensity (I/I ) up
w
0
to 7.88-fold at 410 nm (Fig. 1b). In the solution of SPQ5, white precipitate also
appeared when water content increased over 40%. In addition, the AIE feature of
SPQ5 could be directly observed by the fluorescence color changes taken under 365
nm UV lamp (Fig. 1b, inset). The fluorescence quantum yields of SPQ5 in pure DMF
and DMF/water binary solution (f = 20%) were determined as 11.24% and 37.8%,
w
respectively, according to the corresponding formula [79], using quinine sulfate as
standard.
Fig. 1
In order to further explore the AIE properties of SPQ5, XRD, Tyndall phenomenon

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and SEM had been carried out. In the XRD spectra (Fig. S6), the powder of
chemosensor SPQ5 obtained from DMF had weakly signal peak. However, the
powder obtained from DMF/H O (8:2, v/v) binary solution of SPQ5 clearly shown
2
significant pick at 2θ = 23.25º and 2θ = 24.15º (d= 3.82 Å and 3.68 Å). Above result
attributed to enhancement of π-π stacking with increasing of water content.
Interestingly, with increasing of the water content, especially when the water content
reached 20%, a significant Tyndall phenomenon (Figure 2a) was observed in
DMF/H O binary solution, indicating that the aggregation of SPQ5 induced
2
enhancement of AIE fluorescence. Meanwhile, after aggregation of SPQ5 in
DMF/H O binary solution, the surface morphology of SPQ5 changed from irregular
2
block (Fig. 6a) to coral-like structure (Figure 2a), which also indicates the formation
of supramolecular polymers by aggregation of SPQ5 in DMF/H O (8:2, v/v) binary
2
solution, supporting the correctness of above self-assembly mechanism.
1
The AIE activity of chemosensor SPQ5 was also investigated. By H NMR titration
1
methods, the aqueous-content-dependent H NMR titration spectra (Fig. 3) provided
important insights into their AIE behaviors, with the addition of D O, the hydrogen
2
protons (H , H , H H and H ) on the 8-hydroxyquinoline downfield 0.02, 0.03, 0.04
2
3
4,5
6
1
0
8
.03 ppm and upfield 0.03 ppm, respectively (Fig. 3), which could attributed
-hydroxyquinolines moiety through π-π stacking interaction self-assembled into a
supramolecular dimer. Meanwhile, the protons of aryl hydrogen of pillar[5]arene of
cavity (Ha), chain alkyl(Hd), methoxy(Hc) and methylene hydrogen(Hb) upfield 0.01,
0
.01, 0.03 and 0.02 ppm, respectively, indicated that a supramolecular network was

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formed by π-π stacking between the cavities of the pillar[5]arene and driven by
multiple C-H···π interactions between cavities of the pillar[5]arene and methoxy
protons (Scheme 2c).
Fig. 2
The fluorescence behavior of SPQ5 towards metal ions was carried out in
DMF/H O (8:2, v/v) binary solution. The recognition profiles of the chemosensor
2
2
+
2+
2+
2+
2+
2+
+
2+
2+
SPQ5 towards various cations (Zn , Pb , Cd , Ni , Co , Hg , Ag , Ca , Mg ,
3
+
2+
3+
3+
3+
3+
Cr , Ba , Tb , Eu , La and Al ) were primarily investigated using fluorescence
2
+
spectra (Fig. 4), when 2.0 equiv. of the various cations were added, only Hg could
significantly quench the fluorescence, immediately. Meanwhile, blue fluorescence
disappeared was observed under UV lamp (Fig. 4 Inset), the fluorescence intensity of
the peak at 410 nm sharply decreased, which indicated that the chemosensor SPQ5
2
+
2+
changed into metal coordination polymer SPQ5-Hg . As a result, the Hg could be
easily detected through the fluorescent color of SPQ5 solution transformation from
blue to colorless under the UV lamp. The fluorescence spectral properties of
2
+
chemosensor SPQ5 towards Hg were also carried out in the solution of DMF/H O
2
(8:2, v/v), which we got the same experiment phenomenon as the above situation. In
2
+
order to investigate the binding properties of the receptor SPQ5 towards Hg ,
fluorescence titration of SPQ5 has been carried out in DMF/H O (8:2, v/v) binary
2
solution. As shown in Fig. S4, the spectral emission intensity of SPQ5 quenched with
2
+
the addition of Hg . In the fluorescence spectra, upon addition of increasing amounts
2
+
of Hg (0-1.73 equiv.) to the solution of SPQ5 in DMF/H O (8:2, v/v), the
2

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fluorescence emission at 410 nm showed a dramatic fluorescence quenching by 92%
(
quenching efficiency (I-I )/I×100% = 92%). The detection limit of the fluorescent
0
-8
2+
spectra changes calculated on the basis of 3σ/S is 2.53×10 M for Hg (Fig. S8),
which is lower than other various reported methods (Table 1). The lower detection
2
+
limit revealed the high sensitivity of SPQ5 towards Hg . In addition, when the
2
+
amount of Hg is beyond 1.73 equiv., the emission at 410 nm tends to saturation.
2
+
Furthermore, in order to quantify the complexation ratio between SPQ5 and Hg , the
2
+
Job's plot was conducted by varying the concentration of both SPQ5 and Hg (Fig.
2
+
2+
S9), the turning point appears at the mole fraction of 0.33 equiv. (Hg /SPQ5-Hg )
2
+
indicates that SPQ5 and Hg formed a 2:1 complex.
Fig. 3
Moreover, the successive recognition property of SPQ5 towards cations was further
2
+
2+
2+
2+
2+
+
2+
2+
investigated by adding various cations (Zn , Pb , Cd , Ni , Co , Ag , Ca , Mg ,
3
+
2+
3+
3+
3+
3+
2+
Cr , Ba , Tb , Eu , La and Al ) into SPQ5-Hg DMF/H O (8:2, v/v) binary
2
2
+
solution. As a result, SPQ5 could detect Hg with specific selectivity and the
addition of other cations have no effect on recognition performance (Fig. 5). Due to
2
+
the SPQ5 showing excellent “turn off” response to Hg , we rationally introduced
2
+
2+
competitive coordination properties by adding Hg into SPQ5 to prepare SPQ5-Hg .
2
+
Interestingly, SPQ5-Hg showed single guest-response properties, by adding various
-
-
-
-
-
-
-
-
-
-
-
-
anions including F , Cl , Br , I ,AcO , HSO , H PO , ClO , CN , SCN , N and OH
4
2
4
4
3
2
+
(
4 equiv.) into the solution of SPQ5-Hg in DMF/H O (8:2, v/v). For an instant, the
2
2
+
-
SPQ5-Hg could selectively fluorescence “turn-on” sensor CN (Fig. S10).

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2
+
-
In order to examine the efficiency between SPQ5-Hg and CN , fluorescence
emission titration experiment was monitored. In the fluorescence titration spectra,
-
with an increasing amount of CN (0-4.8 equiv.), the fluorescence emission bands at
4
10 nm appeared gradually. (Fig. S11). Meanwhile, the fluorescence detection limit
-8
-
was calculated on the basis of 3σ/S is 7.71×10 M for CN by fluorescence titrations
2
+
-
(
Fig. S12), which indicates that SPQ5-Hg could detect CN lower than previous
reported [80-81]. To validate the selectivity of sensor SPQ5, the same tests were
-
-
-
-
-
-
-
-
-
-
-
applied using F , Cl , Br , I , AcO , HSO , H PO , ClO , SCN , N and OH (4
4
2
4
4
3
equiv.). None of these anions induced any significant changes in the fluorescent
spectrum of the sensor progress (Fig. S13). From the bar diagram, we could easily
2
+
-
consider that the effects on emission intensity of SPQ5-Hg and CN aqueous
solutions upon addition of various anions were almost negligible. Therefore, it was
-
clear that other anions didn`t interfer during the detection of CN .
Fig. 4
This fluorescence “on-off-on” phenomenon was induced by the competitive
2
+
-
2+
-
coordination of Hg and CN . The Hg competitive coordination with CN lead to
2
+
the fluorescent of SPQ5 solution recovered. Therefore, the solution of SPQ5-Hg
-
2+
could “turn on” sense CN with specific selectivity. Thus, SPQ5 could act as Hg and
-
CN controlled “on-off-on” fluorescent chemosensor. The repeated switching behavior
2
+
-
when altering adding amounts of Hg and CN into the solution of SPQ5, evidently
2
+
proved the excellent reusability and stability of SPQ5 towards Hg at least for three
successive cycles (Fig. S14).

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Scheme 2
1
In addition, we investigated the florescent “on-off-on” behavior mechanism, the H
1
NMR titration spectra were carried out. In the H NMR titration spectra (Fig. S15),
2
+
with the addition of Hg , the significant downfield shift of resonance signals （H ）
1
-6
2
+
on 8-hydroxyquinoline was observed. The results confirmed SPQ5-Hg complex
2
+
constructed by the coordination interaction of O and N with Hg on the quinoline
2
+
group [82]. The XRD spectra of SPQ5-Hg showed no insignificant peaks (Fig. S17)
2
+
also indicated that the SPQ5 complexed with Hg and π-π staking between
-hydroxyquinoline was destroyed. Meanwhile, C-H···π interaction of pillar[5]arene
was broken, resulting in the solution of SPQ5 fluorescence quenching (Scheme 2d).
8
-
2+
After addition of 4 equiv. of CN into SPQ5-Hg , the 8-hydroxyquimoline
hydrocarbon signals H1-6 have a signifcant upfeld shift 0.06, 0.24, 0.34, 029, 0.18 and
0
.18 ppm, respectively (Fig. S16). Indicating the formation of Hg(CN) complex
2
-
2+
between CN and Hg . Meanwhile, both aryl hydrogen of Pillar[5]arene (Ha) and
methylene bridge hydrogen (Hc) upfeld shift 0.04ppm. Demonstrating that π-π
stacking interactions of pillar[5]arene was recovered , which was shown in Scheme 2.
We could also see this from XRD spectra (Fig. S17).
Fig. 5
To get deep insight into the morphological features of the powder SPQ5, SEM
studies were carried out. As we could see in Fig. 6a, the images of SPQ5 showed
irregular block structure, when it was treated with DMF/H O (8:2, v/v) binary
2
solution, the morphology of SPQ5 presented tight coralline structure (Fig. 2b),

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indicating that the SPQ5 self-assembled into two-dimensional supramolecular
polymer chain, we also found that the SPQ5 formed π-π stacking and C-H···π
interactions with the pillar[5]arene, leading to the formation of three dimensional
2
+
supramolecular polymer networks. After adding Hg into SPQ5 (Fig. 6b), the tight
2
+
coralline structure changed into lamellar structure means the formation of Hg and
quinolone coordination interaction resulting in the π-π stacking interactions between
2
+
-
quinoline has been destruction. Otherwise, when SPQ5-Hg was treated with CN
(Fig. 6c), the image was transformed into a stick fiber structure due to the competitive
-
2+
2+
complexation of CN to Hg from SPQ5-Hg coordination polymerization.
Fig. 6
2
+
-
The self-assembly process of chemosensor SPQ5 with Hg and CN was also
investigated by the XRD patterns (Fig. S17). The XRD patterns obtained from
DMF/H O (8:2, v/v) binary solution of SPQ5 clearly showed a typical diffraction
2
peaks at 2θ = 23.25º and 2θ = 24.15º (d= 3.82 Å and 3.68 Å), indicating that π-π
stacking interactions existed in the pillar[5]arene groups and 8-hydroxyquinoline
2
+
groups (Scheme 2c). Otherwise, the in-significant peaks of SPQ5-Hg indicated that
π-π stacking was destroyed. What’s more, the reappeared d-spacing of 3.83 Å at 2θ =
-
2+
2
2.92° means π-π stacking recovered when the CN was added into SPQ5-Hg .
Since the fluorescence emission of SPQ5 could be accurately controlled by
2
+
-
alternative addition of Hg and CN , the fluorescence emission of SPQ5 could be
defined as the logic gate output, which provides an entry for developing a
2
+
-
supramolecular logic gate using Hg (Input 1) and CN (Input 2) as two inputs. We

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have designed a type of IMP logic gate (Fig. 7). For inputs, the addition and the
2
+
-
absence of Hg and CN could be defined as 1 and 0, respectively. For output, we
defined the normalized fluorescence intensity of SPQ5 turn on as “1” and turn off as
“0”. Based on the above definitions, the fluorescence quenching of SPQ5 is observed
2
+
only in the addition of Hg , so that the output is read as 0. Under other circumstances,
the fluorescence of SPQ5 is not quenched leading to the output being read as 1. From
2
+
the truth table of Fig. 7a, it is observed that addition of only Hg (Input1 = 1 and
Input 2 = 0) causes a low fluorescence intensity value implying that the output signal
is below the threshold value (output = 0). With other possible input combinations ((0,
0
), (0, 1), and (1, 1)), the output signal is above the threshold value i.e. the output = 1.
Hence, by monitoring the fluorescence intensity change of 1 at 410 nm by the two
2
+
-
inputs (Hg and CN ); an IMP logic gate can be viewed.
Fig. 7
2
+
Moreover, in order to facilitate the applying of chemosensor SPQ5, the Hg test
kit was prepared by loading SPQ5 on a silica gel plate (Fig. S18). The silica gel
plate-based SPQ5 test kit exhibits fascinating fluorescence emission, upon dipping
-8
2+
the test kit into the different concentrations (from 1 M to 1×10 M) of Hg aqueous
solutions, distinct levels of brilliant fluorescence emission appeared under UV lamp.
Therefore, the SPQ5 based silica gel plates could act as a novel and efficient test kit
2
+
for convenient detection of Hg with high sensitivity.
4
. Conclusions
In summary, we have rationally designed and synthesized a novel

ACCEPTED MANUSCRIPT
8
-hydroxyquinoline functionalized pillar[5]arene (SPQ5). It shows blue AIE
fluorescence in DMF/H O (8:2, v/v) binary solution by π-π stacking and C-H···π
2
interactions. Meanwhile, chemosensor SPQ5 shows highly selective and sensitive
2
+
fluorescence ‘‘on-off’’ behaviour toward Hg over other cations. The in situ prepared
2
+
-
SPQ5-Hg complex exhibits high selectively and sensitively to CN over other
2
+
anions through a complexation reaction. The detection limit of SPQ5 for Hg and
-
-8
-8
CN are as low as 2.53×10 M and 7.71×10 M, respectively. Furthermore other
anions and cations had little influence on the probing behaviour. Moreover, the
2
+
-
fluorescence changes of SPQ5 upon the addition of Hg and CN were utilized as an
2
+
-
IMP logic gate at the molecular level, using Hg and CN as chemical inputs and the
fluorescence intensity signal as the output. Notably, the actual usage of chemosensor
SPQ5 was further demonstrated by test kits and silica gel plates which could
2
+
convenient and efficient detect toxic Hg in aqueous media.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
This work was supported by the National Natural Science Foundation
of China (NSFC) (Nos. 21662031; 21661028; 21574104) and the
Program for Changjiang Scholars and Innovative Research Team in
University of Ministry of Education of China (NO. IRT 15R56).

ACCEPTED MANUSCRIPT
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