AIE-active tetraphenylethene functionalized metal-organic framework for selective detection of nitroaromatic explosives and organic photocatalysis

Article abstract of DOI:10.1039/c6cc04997d

AIE-active luminogen tetraphenylethene (TPE) was incorporated into a UiO-isoreticular zirconium metal-organic framework via the strategy of mixed dicarboxylate struts, and the resulting functionalized MOF shows a strong blue-green emission and selective s

Full text of DOI:10.1039/c6cc04997d

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DOI: 10.1039/C6CC04997D
Journal Name
COMMUNICATION
AIE-active tetraphenylethene functionalized metal-organic
framework for selective detection of nitroaromatic explosives and
organic photocatalysis†
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
a
a
a
a
b
DOI: 10.1039/x0xx00000x
Qiu-Yan Li,‡ Zheng Ma,‡ Wen-Qiang Zhang, Jia-Long Xu, Wei Wei, Han Lu, Xinsheng Zhao
a
and Xiao-Jun Wang*
www.rsc.org/
AIE-active luminogen tetraphenylethene (TPE) was incorporated rigid porous MOF matrixes would endow them the superior
1
0
into UiO-isoreticular zirconium metal-organic framework via the luminescent properties for specific applicaitons. Dincǎ et al
strategy of mixed dicarboxylate struts, which shows a strong blue- reported the first example of TPE-based luminescent MOF by
green emission and selective sensing of nitroaromatic explosives using a newly designed tetrakis(4-carboxyphenyl)ethylene
2
,4,6-trinitrophenol (TNP) and 2,4-dinitrophenol (DNP) through ligand, which shows the potential utility toward sensing of
10a
fluorescence quenching. Moreover, the luminescent MOF exhibits small organic molecules.
Subsequently, Zhou and his co-
efficient
photocatalytic
activities
for
aerobic
cross- workers have utilized an extended TPE-based carboxylate
dehydrogenative coupling reactions mediated by visible light.
linker to react with ZrCl in the presence of variable competing
4
acid, giving rise to two robust and highly fluorescent Zr-MOFs
10e,10f
Metal-organic frameworks (MOFs) are composed of multi-
dentate organic linkers and inorganic metal nodes,
representing a novel class of porous crystalline materials. Due
with different topologies.
More interestingly, one of the
two MOFs, PCN-128, exhibited a unique piezofluorochromic
1
1
0f
behavior under the pressures. Also, pyridyl-decorated TPE-
based ligand was employed by Li’s group to construct
luminescent MOF for highly effective and selective detection
to their well-ordered structures, high porosity and adjustable
organic ligands/metal clusters, MOFs have demonstrated the
2
-7
2
1
0g
great promise for diverse applications, such as gas storage,
of mycotoxins.
3
4
5
separation, light harvesting, heterogeneous catalysis and
biomedical related area. Recently, a kind of fascinating
These reported pioneering examples have revealed the
charm of MOFs integrating with AIE, however, this fantastic
research field is still in its infancy stage. Thereby, much more
effort should be devoted into such active area for developing
multifunctional luminescent MOFs, as well as further exploring
their other applications apart from the chemical sensing. This
may largely depend on the development of novel ligands with
6
luminescent MOFs has been developed for achieving the
purpose of light-emitting, detection/sensing and even photo-
catalysis, through the introduction of various photoactive
components including rare-earth metal ions, fluorescent
8
ligands or encapsulated dye species.
11
It seems that rigidifying fluorescent linkers within MOFs is
much more appealing, which usually reduces their non-
radiative decay rate and results in increased quantum
efficiencies. However, many conventional luminophores suffer
from the reduced emission in the condensed phase due to the
AIE properties.
9
aggregation-caused quenching (ACQ) effect. In contrast, some
molecules featuring aggregation-induced emission (AIE)
characteristics, such as tetraphenylethylene (TPE), exhibit
9
highly enhanced emission in the aggregate state. Thus, it can
be expected that the introduction of AIE-functional cores into
Scheme 1 Synthesis of mixed strut MOF UiO-68-mtpdc/etpdc.
Herein, we designed and synthesized an AIE-active TPE-
conjugated terphenyldicarboxylate linker, denoted as H -etpdc;
2
then, a UiO-isoreticular zirconium MOF was successfully
constructed by the solvothermal reaction of ZrCl with the
4
mixture of struts H -etpdc and H -mtpdc via the mix-and-
2
2
1
2
match approach (Scheme 1). The new TPE-functionalized Zr-
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MOF, denoted as UiO-68-mtpdc/etpdc, exhibits a strong blue- material. Thus, we investigated its chemo-sensingVbieewhAartviciloe rOsnlbinye
green emission, which can be used to selectively detect using 2,4,6-trinitrophenol (TNP) as an DeOxpI:l1o0s.1iv0e39/mC6oCdCe0l.49It97iDs
nitroaromatic explosives 2,4,6-trinitrophenol (TNP) and 2,4- found that the dispersion of MOF UiO-68-mtpdc/etpdc in
dinitrophenol (DNP) via fluorescence quenching. Moreover, CH OH also exhibits a strong emission centered at 490 nm,
3
the MOF can work as a highly active photocatalyst for visible which can be quickly and dramatically quenched by
light promoted aerobic cross-dehydrogenative coupling (CDC) incremental addition of TNP into the suspension (Fig. 1a).
reactions. To our knowledge, this is the first study of AIE-core When the concentration of TNP is as low as 40 ppm, the initial
functionalized MOF in the application of organic photocatalysis. PL intensity is quenched over 50%, indicating that UiO-68-
The new ligand H -etpdc was conveniently obtained via mtpdc/etpdc is highly sensitive towards TNP. And the Stern-
2
4
several typical organic reaction steps as described in Scheme Volmer quenching constant (k ) was estimated to be 2.8 × 10
S1 (for details, see ESI). Initially, we found that the direct
solvothermal reaction of ZrCl4 and H -etpdc in N,N’- based sensors. Besides, we found that 2,4-dinitrophenol (2,4-
sv
-
1
M for TNP, which is comparable with other reported MOF-
1
4
2
dimethylformamide (DMF) failed to give the desirable DNP) and p-nitrophenol (p-NP) can also efficiently quench the
4
-
crystalline UiO MOF, presumably due to the steric bulk of TPE emission of UiO-68-mtpdc/etpdc with k values of 2.3 × 10 M
sv
1
3
-1
moiety of organic linker. Thus, a combination of H -etpdc and
and 7.2 × 10 M (Fig. S11 and S12 in ESI), respectively. And
2
H -mtpdc in 1:1 molar ratio was treated by ZrCl in DMF at 100 the fluorescence quenching degrees in the presence of
2
4
o
13
C to produce UiO-68 derivative MOF UiO-68-mtpdc/etpdc
nitrophenol species with the same concentration of 100 μM,
(for detail, see ESI). Such a mixed-strut approach can allow for are 92%, 76% and 42% for TNP, DNP and p-NP, respectively. In
accommodation of the relatively sterically demanding TPE contrast, the quenching degree by other nitrobenzene
motif within the parent framework, while maintain the compounds, such as 2,4,6-trinitrotoluene (TNT), 2,4-
porosity and open pores of framework to facilitate substrate dinitrotoluene (DNT),
1,3-dinitrobenzene (DNB), o-
diffusion for achieving efficient catalysis. Powder X-ray nitrotoluene (o-NT), m-nitrotoluene (m-NT), p-nitrotoluene (p-
diffraction (PXRD) of UiO-68-mtpdc/etpdc revealed its highly NT), nitrobenzene (NB), are much lower under otherwise
crystalline nature and isostructure with the parent framework identical condition (Fig. 2b and Fig. S13 in ESI). These results
UiO-68 (Fig. S1 and S2 in ESI). Additionally, nitrogen sorption indicate that UiO-68-mtpdc/etpdc offers a selective sensing of
investigation at 77 K exhibited a typical type I isotherm with nitrophenols, such as TNP and DNP, among the above
2
-
1
BET surface area of 960 m g (Fig. S5 in ESI), confirming the nitroaromatics. Such high selectivity of the MOF towards
high porosity of UiO-68-mtpdc/etpdc.
nitrophenols over other nitroaromatics, could be attributed to
the electrostatic and/or hydrogen-bonding interactions
between the acidic hydroxyl group of nitrophenols and Lewis
1
4,15
basic N-donor sites of imidazole in etpdc ligand (Fig. 2),
which was also confirmed by density functional theory (DFT)
1
6
calculations at the B3LYP/3-21G level (Fig. S14 in ESI). The
strong interactions would facilitate the electron and energy
transfer process from the electron-rich TPE moiety to electron-
deficient nitrophenols, thus, leading to the highly effective and
selective quenching response.
3
Fig. 1 (a) Emission spectra of MOF UiO-68-mtpdc/etpdc dispersed in CH OH (0.02
mg/mL) upon incremental addition of TNP. Inset: corresponding Stern-Volmer plot of
the quenching fluorescence intensity as function of TNP concentration. (b)
Percentage of fluorescence quenching obtained for different nitroaromatic compounds
a
O2N
NO2
(100 μM). Excited at 370 nm.
H
O
N
NO2
N
H
As expected, the TPE-integrated MOF UiO-68-mtpdc/etpdc
shows a strong blue-green emission centered at 490 nm with a
quantum yield (Φ) of 48% in the solid state (Fig. S6 and S7 in
ESI). In comparison, its linker precursor H -etpdc exhibits the
2
emission maxima at 518 nm with Φ value of 32%. The blue
Weak Emission
shift and quantum yield enhancement of UiO-68-mtpdc/etpdc
Fig. 2 Schematic representation of electrostatic and hydrogen-bonding interactions
between TNP and etpdc-linker in MOF UiO-68-mtpdc/etpdc.
should be attributed to the immobilization of H -etpdc linker in
2
rigid framework, which was also observed in other reported
9,10
10e
TPE-core based MOFs,
such as PCN-94. Furthermore,
Subsequently, in order to further explore applications of
AIE-integrated MOFs, UiO-68-mtpdc/etpdc was tentatively
used as photocatalyst to promote aerobic CDC reactions,
which involve the direct formation of C-C bond via two C-H
both H -etpdc and UiO-68-mtpdc/etpdc exhibit a similar
2
biexponential fluorescence decays comprised of one short τ1
and a longer τ (Table S1 in ESI), which can be attributed to
2
10a
monomer and excimer fluorescence lifetimes, respectively.
1
7
bonds under oxidative conditions. The initial study was
performed by a typical model cross-coupling reaction of N-
phenyl-1,2,3,4-tetrahydroisoquinoline (1a) with indole (2a) at
The highly photoluminescent (PL) efficiency makes UiO-68-
mtpdc/etpdc serve as a promising luminescent-based sensory
2
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ambient temperature (Scheme 2). When the reaction in ESI), indicating the important role of molecular oxygen for
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mixture in the presence of a catalytic amount of UiO-68- the aerobic CDC reaction. Thus, elDeOcIt:r1o0n.103p9a/Cra6mCCa0g4n9e9t7iDc
mtpdc/etpdc was irradiated by blue LEDs (λmax = 450 nm) for resonance (EPR) experiments were performed to determine
several hours, to our delight, the desired product 3a can be the active species of oxygen in the photocatalysed process, in
readily obtained (Table S2 in ESI). And a yield of ~93% was which 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) and 2,2,6,6-
obtained after optimization of irradiation time and amount of tetramethyl-1-piperidine (TEMP) were employed to capture
•
−
1
MOF. Control experiments revealed that each element of the superoxide radical anion O2 and singlet oxygen O ,
2
CDC reaction, including photocatalyst, light and oxygen, is respectively. As shown in Fig. 3, no signal was observed upon
indispensable for the efficient progress of the aerobic coupling irradiation of the mixture containing TEMP and UiO-68-
reaction. Moreover, no catalytic activity was observed when mtpdc/etpdc in the absence or presence of 1a, indicating no
1
using MOF UiO-68-mtpdc as photocatalyst that only contains
O formation in the process. There was also no signal when
2
1
2d
the ligand H -mtpdc.
This confirms that AIE-active TPE DMPO was added into CH OH solution of UiO-68-mtpdc/etpdc.
moiety in MOF UiO-68-mtpdc/etpdc works as an active Whereas the signal of O2 captured by using DMPO as a
2
3
•
−
photocatalytic center for driving the reaction.
radical scavenger was clearly detected in the presence of 1a
This revealed that there is an effective single electron transfer
SET) from 1a to excited TPE-integrated MOF UiO-68-
mtpdc/etpdc (PC*) upon irradiation, along with the formation
.
(
•
+
•−
of radical cation 1a and radical anion PC (Scheme 3). The
•
−
generated PC subsequently reacts with oxygen to produce
•
−
•+
O2 , which abstracts a proton from 1a to afford intermediate
Scheme 2 The model CDC reaction of N-phenyl-1,2,3,4-tetrahydroisoquinoline (1a) with
indole (2a) catalysed by MOF UiO-68-mtpdc/etpdc under visible light.
•
•
1
a
. Furthermore, the radical 1a was oxidized to the imine
+
cation 1a that was attacked by nucleophile to afford the
product.
The heterogeneous nature of UiO-68-mtpdc/etpdc catalysis
was confirmed by filtration reaction and results of recycle
catalysis. The MOF photocatalyst was removed from the
reaction system after 5 h, which was followed by another 8 h
of irradiation. Almost no more production of 3a was observed,
indicating no leaching of active catalyst species into solution as
well as the heterogeneity of MOF UiO-68-mtpdc/etpdc during
photocatalysis. Meanwhile, the reusability of UiO-68-
mtpdc/etpdc as a heterogeneous catalyst for the coupling
reaction was investigated, which can be readily recovered
from the reaction mixture by centrifugation. And the catalyst
can be at least reused five times without loss of activity (Fig.
S15 in ESI). In addition, PXRD pattern of UiO-68-mtpdc/etpdc
after five cycles revealed no deterioration of crystallinity (Fig.
S16 in ESI), mainly due to the robust Zr-based UiO
Scheme 3 Proposed mechanism for the photocatalytic aerobic CDC reaction by MOF
UiO-68-mtpdc/etpdc (photocatalyst, PC).
1
9
framework.
Considering the highly catalytic activity and recyclability of
MOF UiO-68-mtpdc/etpdc based photocatalyst, along with
well understanding of the reaction mechanism, we further
examined the scope of the coupling reaction photocatalyszed
by the MOF. As shown in Table S3 and Table S4 (in ESI), most
of the CDC reaction between a variety of substituted
tetrahydroisoquinoline derivatives with different nucleophilic
indoles and nitroalkanes gave good-to-excellent yields.
In summary, we have designed and synthesized an AIE-
active TPE-conjugated terphenyldicarboxylate strut, which was
successfully incorporated into the robust UiO-68-based
framework through a mix-and-match strategy using the mixed
dicarboxylate struts. Due to the restricted intramolecular
rotation of AIE-characteristic TPE unit in rigid framework, the
Fig. 3 EPR measurements of a solution in CH
and with 1a (b) in the presence of TEMP upon the irradiation of blue LEDs for 60 s; a
solution in CH
presence of DMPO upon the irradiation of blue LEDs for 60 s. In air atmosphere.
3
OH of UiO-68-mtpdc/etpdc without 1a (a)
3
OH of UiO-68-mtpdc/etpdc without 1a (c) and with 1a (d) in the MOF shows a strong blue-green emission, which can further be
used for the selective and sensitive detection of nitrophenol
type explosives via a luminescence quenching. Moreover, the
We have found that almost no photoproduct was detected TPE-based MOF have demonstrated a highly catalytic activity
when the reaction was conducted in N atmosphere (Table S2 for visible light-driven aerobic CDC reactions between tertiary
2
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A. F. Cozzolino, V. K. Michaelis, R. G. Griffin andVieMw A.rDticilne cOan,linJe.
amines and different carbon nucleophiles. To the best of our
knowledge, this is the first demonstration of MOF integrated
AIE-core for organic photocatalysis. Furthermore, it can be
expected that more MOFs incorporated AIE-luminogens would
be developed for various applications in the near future.
This work was financially supported from NSFC (21302072
and 51403081), NSF of Jiangsu Province (BK20130226), TAPP
and PAPD of Jiangsu Higher Education Institutions. We are very
grateful to Dr. Ying Wang in Beijing Normal University for the
assistance in DFT calculation.
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