Luminescent cyclic trinuclear coinage metal complexes with aggregation-induced emission (AIE) performance

Article abstract of DOI:10.1039/c8dt04898c

A series of AIE active cyclic trinuclear complexes (Au₃, Ag₃, and Cu₃) have been successfully prepared and elucidated by X-ray crystallography. These complexes showed excellent AIE properties and their quantum yields (QYs)

Full text of DOI:10.1039/c8dt04898c

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DOI: 10.1039/C8DT04898C
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Luminescent Cyclic Trinuclear Coinage Metal Complexes with
Aggregation-Induced Emission (AIE) Performance
Yuan Tiana, Zhao-Yang Wang*a, Shuang-Quan Zang*a, Dan Li*b and Thomas C. W. Maka,c
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
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A series of AIE active cyclic trinuclear complexes (Au3, Ag3, and
Nevertheless, a majority of the AIE active molecules are
Cu3) have been successfully prepared and elucidated by X-ray organic and this phenomenon have been rarely explored for
crystallography. These complexes showed excellent AIE properties metal complexes.6 Not to mention AIE luminescent materials
and their quantum yields (QYs) were significantly increased with precise structures have been synthesized.7 In addition,
compared to that of the free ligands. The remarkable solution compared with the conventional chromophores, luminescent
induced AIE activity in atom-precise coinage metal complexes is metal complexes do have better photostability, which may
still scarce, and this work opens a promising avenue for the result in much better performance in catalytic processes and
development of easily prepared metal-based AIE luminogens with optoelectronics (e.g., LEDs).8 Coinage metal complexes have
high emission efficiency.
attracted extensive interest in recent years owing to their
novel properties and potential applications in various fields.9,10
Among these physical/chemical properties, luminescence
represents one of the most intriguing features of these
materials.11 However, a technical challenge is that the
photoluminescence of coinage metal complexes are often
weak, and their quantum yields (QYs) rarely exceed 0.1%.
Recently, the discovery of AIE phenomenon can be used to
design high-luminescence metal complexes to address these
obstacles.12 Xie and co-workers have synthesized Au22(SG)18
clusters, which showed red emission with a QY of ∼8%. By
comparison with those of Au(I)−thiolate complexes, their
stronger luminescence intensity was ascribed to AIE. However,
the origin of emission in these clusters still remains
unaddressed, what makes a major hurdle for the design of
excellent AIE materials.13 Therefore, it remains a further
advance to develop a method for the rational design of
coinage metal complexes with excellent AIE properties.4b,14
Herein, we successfully synthesized a series of prominent
Luminogens with aggregation-induced emission (AIE)
properties have emerged as a new class of luminescent
materials which have shown great possibility to be widely
utilized as optoelectronic devices and sensory systems, etc.1
The AIE effect is considered constructive because the
photoemission of the propeller-like molecules could be
significantly enhanced after aggregation, which greatly differs
from the aggregation-caused quenching (ACQ) observed in
many conventional chromophores that possess planar and
well-conjugated structures.2 In general, conventional
luminogens only exhibit efficient emission in a molecularly
dispersive state and the aggregation of the molecules should
be strictly avoided, which could lead to an obstruction of
applications.3 The discovery of the fantastic AIE phenomenon
furnishes a high possibility of conquering the ACQ problem.4
Therefore, various AIE luminescent materials have been
designed and synthesized, among which hexaphenylsilole
(HPS), tetraphenylethene (TPE) and distyreneanthracene (DSA)
moieties are typical representatives.4a,5
AIE
active
coinage
metal
complexes,
namely
and
[Au3(DTBP)3]·CH2Cl2·CHCl3,
[Ag3(DTBP)3]·2CHCl3
[Cu3(DTBP)3]·2CHCl3 (denoted as M3, M = Au, Ag or Cu), by
reacting 3,5-dimethyl-4-(4-(1,2,2-triphenylvinyl)benzyl)-1H-
pyrazole (DTBP) with coinage metal ions in the presence of
triethylamine (Figure 1a). All of these complexes have been
successfully elucidated by X-ray crystallography. The triangular
assemblies of coinage metal atoms and pyrazole groups
promoted the formation of ordered layered structure which
increased the restriction of intramolecular rotations (RIR)
effect of AIE-active units, thus effectively restricted non-
radiative decay. Therefore the process promoted highly
a. College of Chemistry and Molecular Engineering, Zhengzhou University,
Zhengzhou 450001, China.
E-mail: wangzy@zzu.edu.cn, zangsqzg@zzu.edu.cn
b. College of Chemistry and Materials Science, Jinan University, Guangzhou 510632,
P. R. China.
E-mail: danli@jnu.edu.cn
c. Department of Chemistry, The Chinese University of Hong Kong, Shatin, New
Territories, Hong Kong.
Electronic Supplementary Information (ESI) available: Experimental details, crystal
data and additional figures. CCDC Au3 (1881605), Ag3 (1881607) and Cu3
(1881606). For ESI and crystallographic data in CIF See DOI: 10.1039/x0xx00000x
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emissive and strongly AIE response, which led to the QYs reach 490 nm) under UV light (Figure 2), while DTBP ligand showed
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DOI: 10.1039/C8DT04898C
up to 12.01% (Ag3, about 7.5 times to ligand) in the solid state. blue-green emission (λmax = 494 nm) (Figure S10). The similar
Our approach using rigid pyrazolyl ligand paves a new way to profiles indicated that the emissions of complexes are ligand-
construct precise structure coinage metal complexes with centered. Furthermore, the nanosecond-scale emissive
intense luminescence and prominent AIE performance.
lifetime of M3 emission bands (e.g., τ Ag3 = 6.42 ns) (Figures
S11−13) and DTBP emission bands (τDTBP = 2.60 ns) (Figure S14)
indicated the characteristics of fluorescence, originating from
ligand emission.7,18
Results and discussion
As a well-known AIE luminogen, TPE has unique structural
characteristics with phenyl rotor, of which the RIR process
leads to AIE effect.1 Irradiation of a dilute tetrahydrofuran
solution (a good solvent of DTBP (<10−3 M)) at 365 nm showed
almost no fluorescence at 474 nm. However, the increasing
amount of water (a poor solvent for DTBP) to the mixed
solution greatly enhanced the blue-green emission intensity
(3.2×104 times), and the QY was measured using an integrating
sphere to be 1.59% in the solid state, indicating its strong AIE
A number of TPE-based discrete organic molecular structures
have been determined by experimental characterization.15
However, coinage metal complexes with precise structure are
still rare. Au3, Ag3 and Cu3 were facilely synthesized via one
-
pot method by reacting stoichiometric coinage metal salts or
precursors with pyrazole ligands in the presence of
trimethylamine.16 Needle single crystals suitable for X
-ray
structural analysis were obtained by recrystallizing the samples
via vapor diffusion of n-hexane into their chloroform solutions
(Supporting Information for details). DTBP was first
behavior (Figures S15−17).
1
Interestingly, M3 complexes suggested a similar emission
pattern with higher fluorescence intensity and QYs compared
to those of the free ligand. The QYs of Au3, Ag3 and Cu3
determined was found to be 6.92%, 12.01% and 9.82% at
room temperature in the solid state, respectively (Ag3, about
7.5 times to ligand), which should be ascribed to the structural
rigidity resulted by the stack between planes, which could
effectively restrict non-radiative decay. Furthermore, the
ordered stack of interlayer can form more stable internal
complexes architecture. Especially, argentophilic interactions
within Ag3 shortened the overall intermolecular Ag(I)···Ag(I)
distances, resulting in the QY higher than that of Au3 and Cu3
(Figure 1b).19
synthesized and its purity was confirmed by H NMR and 13C
NMR (Figures S1 4). The phase purity and chemical formula of
−
Au3, Ag3 and Cu3 were further verified by in situ power X-ray
diffraction (PXRD) patterns, thermogravimetric analysis (TGA)
and elemental analysis (Figures S5−9).
Figure 1. (a) Schematic represented the crystal structures of M3. Thermal ellipsoids set
at 50% thermal probability. (b) Interlayer stacking structure of Au3, Ag3 and Cu3. Color
codes: yellow, Au; green, Ag; brown, Cu; blue, N; gray C (red, M; orange, R = –CH2TPE).
All hydrogen atoms are omitted for clarity.
Single crystal X-ray structure analyses revealed that Au3 and
Ag3 crystallize in triclinic space group P-1, while Cu3 crystallizes
in monoclinic space group P21/c (Table S1). Their asymmetric
units exhibit cyclic trinuclear isostructures (Figure 1a). Three
pyrazole groups uniformly adopt the µ2-η1, η1 ligation mode to
link two metal ions to build a stable triangular plane. Notably,
the Ag(I)···Ag(I) distances between adjacent molecules are
about 3.2879 Å in Ag3, indicating the existence of argentophilic
interactions. However, due to the steric hindrance of TPE
molecules, intermolecular metallophilic interactions are not
formed in the stacked structures of Au3 and Cu3 (Figure 1b).17
Interestingly, in the dispersed state, the stable M3 structures
do not restrict the incorporated TPE molecules (free to rotate)
due to the presence of methylene.
Figure 2. Fluorescence spectra of Au3 (blue curve), Ag3 (red curve), and Cu3 (black curve)
excited (dotted line) at 366 nm in the solid state at room temperature. Inset is the
fluorescence images of Ag3 under 365 nm UV light.
The intense blue-green emission of Ag3 as an example
encouraged us to study its AIE property. The dependence
between the aggregates and luminescence intensity of Ag3 was
detected for the aggregates from solvent-induced aggregation.
As illustrated in Figure 3a, the aggregation degree was
controlled by the polarity of the mixed solvent, which could be
varied by the volume fraction of isopropanol in the solvent ƒe
(ƒe = volisopropanol/voltetrahydrofuran+isopropanol, isopropanol is the
poor solvent). The Ag3 solution turned cloudy with weak blue
The luminescent properties of M3 were further investigated.
M3 crystals emitted intense blue-green luminescence (λmax
=
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emission when ƒe reached 40% due to the initial aggregation. were found to be 5.48%, 7.94% and 3.98%, respectively, with
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-4
When ƒe increased to 70%, the solution showed stronger blue- ƒe = 80% and concentration of 1.57×10DOMI: 1,0w.10h3i9c/hC8aDreT0l4o8w98eCr
green luminescence emission, suggesting the presence of well- than the corresponding QYs in solid state. These results further
dispersed colloids of denser aggregates (Figure 3b). The support the AIE behaviours of these complexes. To keep the
solvent-induced AIE of Ag3 was reversible since decreasing ƒe concentration of DTBP same, the QY of DTBP ligand was found
could re-dissolve the aggregates, thereby annulling the AIE to be 0.84% with a concentration of 4.71×10-4 M.
mechanism and subsequently quenching the luminescence.
The UV−vis spectroscopy was also used to follow the
Photoemission spectra were recorded to interpret the aggregate degree of Ag3 with increasing ƒe, while it showed a
emission changes due to variations in aggregation degree main peak at 314 nm (Figure 3d). When ƒe increased further
(Figure 3c). Before ƒe reached 60%, the luminescence intensity from 50% to 95%, the formation of smaller and denser
increased monotonically with the increase in aggregation aggregates was indicated by bathochromic shifts of the spectra
degree. When ƒe reached 70%, the main peak in the emission (Figure 3d, solid black arrow). In the process, the high polarity
spectrum shifted from 454 (blue emitting) to 473 nm (blue- of the solvent gave impetus of red shift. In addition,
green emitting), which was similar to the photoemission hyperchromic shift of the UV−vis absorption spectra appeared
spectra of DTBP shown in Figure S16, and it could be attributed due to the large increase in background scattering (dotted
to the solvent effect.20 Moreover, the QYs of Au3, Ag3 and Cu3 black arrow).6a
Figure 3. (a) Schematic illustration of solvent-induced AIE properties of Ag3 complex. (b) Digital photo of Ag3 complex (concentration: 2×10-4 M) in mixed solvents with
different ƒe under visible (top row) and UV (bottom row) light. (c) Photoemission spectra and (d) UV−vis absorption spectra of Ag3 in mixed solvents with different ƒe
.
Au3 and Cu3 also showed similar AIE properties. Unlike Au3
and Ag3, dichloromethane was used as good solvent for Cu3, as
Cu3 could be oxidized more easily in THF. Figures S18−20
Conclusions
showed that the Au3 solution was non-luminescent until ƒe
reached 70%, afterwards the solution turned intense blue-
green emission. The spectra showed that their fluorescence
intensity gradually increased (λmax = 469 nm). Correspondingly,
the AIE images of Cu3 had the same pattern with Ag3, as the
λmax = 470 nm until ƒe reached 70% or higher (Figures S21−23).
Therefore, the visible eyesight of these complexes expressed
excellent AIE performance in solution-induced system, and
such AIE luminescent materials could find their applications as
biosensing, bioimaging, and dual-functional utilities.
In summary, we have developed a series of TPE-incorporated
coinage metal complexes Au3, Ag3 and Cu3, which exhibit
excellent AIE performance. Crystal structures of these cyclic
trinuclear complexes were successfully elucidated by X-ray
crystallography. These complexes showed intense ligand-
centered blue-green emission at 490 nm. The coordination
induced intermolecular stacking interactions in these
complexes highly promoted structural rigidity and their QYs
were significantly enhanced (12.01% for Ag3, about 7.5 times
to that of ligand in the solid state). Meanwhile, the
aggregation degree positively correlated with the fluorescence
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intensity, indicating that the solution-induced AIE activity was
significantly affected by the RIR and emissive efficiency
improved in aggregation process. As a new strategy to expand
the field of AIE molecules, the coinage metal complexes
produced precise structure nanomaterials with strong
fluorescence which may be applied to diversified fields.
Moreover, the self-assembly provided a promising method for
enhancing luminescence of AIE molecules in nanoscale
complexes.
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Conflicts of interest
There are no conflicts to declare.
Acknowledgements
This work was supported by the National Science Fund for
Distinguished Young Scholars (No. 21825106), the National
Natural Science Foundation of China (No. 21671175, 21801228),
the Program for Science & Technology Innovation Talents in
Universities of Henan Province (164100510005), the Program for
Innovative Research Team (in Science and Technology) in
Universities of Henan Province (19IRTSTHN022) and Zhengzhou
University.
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Graphical abstract
A series of TPE-incorporated cyclic trinuclear coinage metal
complexes have been prepared, which shows remarkable
aggregation-induced emission performance.
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