A sandwich-shaped M3L2 zinc(II) complex containing 1,3,5-tris(dimethyl(pyridin-3-yl)silyl)benzene: Selective photoluminescence recognition of dIIodomethane

Article abstract of DOI:10.1039/c7dt01138e

Self-assembly of Zn(ClO₄)₂ with 1,3,5-tris(dimethyl(pyridin-3-yl)silyl)benzene (L) as a new C₃-symmetric tridentate N-donor gives rise to a discrete sandwich-shaped M₃L₂ architecture, [Zn₃(

Full text of DOI:10.1039/c7dt01138e

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A sandwich-shaped M L zinc(II) complex contain-
3
2
ing 1,3,5-tris(dimethyl(pyridin-3-yl)silyl)benzene:
selective photoluminescence recognition of
diiodomethane†
Cite this: DOI: 10.1039/c7dt01138e
Sangseok Lee, Haeri Lee and Ok-Sang Jung
*
Received 30th March 2017,
Accepted 5th April 2017
3
Self-assembly of Zn(ClO4)2 with 1,3,5-tris(dimethyl(pyridin-3-yl)silyl)benzene (L) as a new C -symmetric tri-
dentate N-donor gives rise to a discrete sandwich-shaped M
O. Its blue photoluminescence is significantly quenched only by CH
cules, CH Cl , CH Br , CHCl , 1,2-dichloroethane, EtOH, CH CN, benzene, toluene, and phenol.
L
3 2
architecture, [Zn
3
(μ-OH)
3 2 4 3 3
L ](ClO ) ·4CH CN·
DOI: 10.1039/c7dt01138e
2H
2
2 2
I
among the various small mole-
rsc.li/dalton
2
2
2
2
3
3
for the selective photoluminescence recognition of CH I .
Generally, zinc(II) complexes have been investigated and deemed
2
2
Introduction
Diiodomethane (CH I ) is known to be unsafe to human health to be appropriate candidates for tetrahedral-binding Lewis acids,
2
2
1
as well as destructive to the atmosphere’s oxidative capacity.
metalloenzymes, zinc-finger proteins, transmetallation, photo-
Nevertheless, it is a suitable chemical for use in density measure- luminescence materials, and homogeneous catalysts in the trans-
23–31
ments of minerals and as a carbene transfer reactant in esterification of a wide range of esters with alcohols.
2–6
Simmons–Smith-type cyclopropanations.
photo-excitation of CH and its related photo-decomposed
chemical species electrons, CH I cations, and iodomethyl rad-
In recent years, the
2 2
I
2
2
Experimental
7–11
icals has been a hot research topic.
Thus, research chemists
an urgent priority.
Materials and measurements
consider a comprehensive recognition of CH I
2 2
All chemicals including zinc(II) perchlorate hexahydrate
Meanwhile, several recent reports, notably, have demonstrated
(
Zn(ClO ) ), n-butyllithium, and 3-bromopyridine were purchased
that transition metal complexes’ photo-luminescence is useful to
4 2
12–15
from Sigma-Aldrich and used without further purification.
develop sensors for specific chemicals.
To the best of our
1
,3,5-Tris(chlorodimethylsilyl)benzene (2) was prepared via a lit-
knowledge, the field still lacks systematic information on CH2I2
molecule recognition via a novel type of luminescent zinc(II)
complex architecture. Thus far, significant coordination architec-
3
2
erature method. Elemental analyses (C, H, and N) were per-
formed on crystalline samples at the KBSI Pusan Center using a
Vario-EL III analyzer. H (300 MHz) and C (75 MHz) NMR
spectra were obtained on a Varian Mercury Plus 300. Infrared
1
13
5
tures with task-specific reaction-vessel, catalyst, ionophore, mole-
cular capsulation, and molecular recognition functions, tantaliz-
ingly, have been synthesized by self-assembly of zinc(II) ions with
polydentate donors taking into consideration various factors such
as counteranions, mole ratios, reaction temperature, and reaction
(
IR) spectra were recorded on a Nicolet 380 FT-IR spectrophoto-
meter using samples prepared as KBr pellets. Thermal analyses
were undertaken under a nitrogen atmosphere at a scan rate of
1
0 °C min− using a Labsys TGA-DSC 1600. Excitation and emis-
1
16–22
solvents.
In this context, we have carried out preliminary
sion spectra were acquired on a FluoroMate FS-2 spectrofluo-
rometer. Electrospray time of flight ionization mass spec-
trometry (ESI-TOF-MS) was performed on a Synapt G2 mass
spectrometer (Waters) at the Ochang Center, KBSI. Time-
resolved fluorescence spectra were recorded on an FL920-TCSPC
spectrofluorometer (Edinburgh Instruments) using a 375 nm
laser source for excitation, as listed in Table S3.†
research on CH I recognition of the intriguing sandwich-shaped
2
2
M L zinc(II) architecture of a new C -symmetric tridentate ligand.
3
2
3
We describe a new class of this architecture that can be utilized
Department of Chemistry, Pusan National University, Busan 46241, Korea.
E-mail: oksjung@pusan.ac.kr
†
Electronic supplementary information (ESI) available: X-ray crystallographic
data, ORTEP drawings, thermal analysis and differential scanning calorimeter
Synthesis of 1,3,5-tris(dimethyl(pyridin-3-yl)silyl)benzene (L)
data, FT-IR spectra, photoluminescence spectra, and fluorescence lifetime of
To a solution of 3-bromopyridine (2.89 mL, 30 mmol) in dry
diethyl ether (75 mL) under a nitrogen gas atmosphere,
[
3 3 2 4 3 3 2
Zn (μ-OH) L ]–(ClO ) ·4CH CN·2H O. CCDC 1534794. For ESI and crystallo-
graphic data in CIF or other electronic format see DOI: 10.1039/c7dt01138e
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n-butyllithium (12 mL of a 2.5 M solution in n-hexane, methods and refined by full-matrix least squares techniques
3
4
3
0 mmol) was added dropwise at −78 °C. The resulting (SHELXL 2014/07). The non-hydrogen atoms were refined
mixture was allowed to warm to 0 °C, at which temperature it anisotropically, and the hydrogen atoms were placed in calcu-
was stirred for 1 h 30 min. Then, 1,3,5-tris(chlorodimethylsilyl) lated positions and refined only for the isotropic thermal
benzene (15 mL, 10 mmol) was slowly added to the above factors. The crystal parameters and procedural information
yellow suspension at −78 °C, and the reaction mixture was corresponding to the data collection and structure refinement
stirred at room temperature for 12 h. Distilled water (40 mL) are listed in Table S1,† and the relevant bond lengths and
was subsequently added, and the organic layer was separated. angles are listed in Table S2.†
The organic solution was washed with water several times and
then dried over anhydrous magnesium sulfate. Evaporation of
the solvent produced a reddish-brown oil, which was then pur-
ified by column chromatography using ethyl acetate as an
eluent. The resulting solution was evaporated, thus affording
Results and discussion
Synthesis
crystalline solid 1,3,5-tris(dimethyl(pyridin-3-yl)silyl)benzene
3
The novel C -symmetric tridentate 1,3,5-tris(dimethyl(pyridin-
(
L) in 35% yield. Anal. calcd for C27
33 3 3
H N Si : C, 67.03; H, 6.87;
3-yl)silyl)benzene (L) was obtained by three-step synthesis in
N, 8.68%. Found: C, 67.20; H, 6.77; N, 8.70%. ESI-TOF-MS m/z
overall 35% yield. Self-assembly of Zn(ClO ) with the L as a
C -axis tridentate N-donor in an acetonitrile and methanol
3
solution at room temperature produced the discrete sandwich-
4
2
+
+
−1
4
2
1
84.2059 (calc. 484.202 for [L + H ] ). IR (KBr pellet, cm ):
956m, 1574m, 1558w, 1397m, 1372w, 1250m, 1144w, 1123m,
026w, 844s, 828s, 797m, 779s, 762m, 713m, 657m, 623w,
shaped M3L2 architecture of [Zn (μ-OH) L ](ClO ) ·4CH CN·
3
3
2
4 3
3
1
4
22s. H NMR (Me CO-d , 300 MHz,δ): 8.64 (s, 3H), 8.55 (d,
2
6
2H O shown in Scheme 1. The reaction was initially performed
2
3
3
J = 5.1 Hz, 3H), 7.84 (s, 3H), 7.81 (d, J = 5.1 Hz, 3H), 7.30 (dd,
J = 5.1 Hz, 4.2 Hz, 3H), 0.58 (s, 18H). C NMR (CDCl ,
3
in a 1 : 1 mole ratio of Zn(II) : L and the lack of any significant
3
13
effects on the products from either the mole ratio or concen-
trations indicated that the architecture is a thermodynamically
stable chemical species.
7
1
2 MHz, ppm,δ): 154.50, 150.30, 141.90, 140.88, 135.85,
33.00, 123.35, −2.54.
Crystal structures
The crystal structure of [Zn (μ-OH) L ](ClO ) ·4CH CN·2H O
3
3
2
4 3
3
2
consists of three zinc(II) ions, two ligands, three hydroxo
anions, three perchlorate anions, and solvate molecules
(
Fig. 1). The local geometries of the zinc(II) cation is a typical
tetrahedral arrangement with two oxygen atoms from the
hydroxo anions and two nitrogen atoms from the ligands (Zn–
Preparation of [Zn
3
3 2 4 3 3 2
(μ-OH) L ](ClO ) ·4CH CN·2H O
An acetonitrile solution (10 mL) of Zn(ClO
)
4 2
(1.396 g, N = 2.023(3)–2.032(3) Å, Zn–O = 1.899(3)–1.930(3) Å, bond
3
.75 mmol) was slowly diffused into a methanol solution angles around Zn(II) = 102.9(1)–123.3(1)°). The structure has a
10 mL) of L (1.210 g, 2.5 mmol). After 2 days, colorless crystals tripod tridentate ligand, and a 6-membered cyclic Zn (μ-OH)
suitable for X-ray crystallography were obtained (2.213 mg, 52% motif (Zn⋯Zn = 3.3803(6)–3.4284(6) Å; see ESI Fig. S1†), and
yield). Mp 333 °C (dec.). Anal. calcd for C62 Zn
thus forms a sandwich-type M architecture. The Zn (μ-OH)
C, 43.92; H, 4.93; N, 8.26%. Found: C, 44.20; H, 4.70; N, 8.13%. ring adopts a puckered-conformation, which is similar to that
(
3
3
H
83Cl
3
N
10
O
16Si
6
3
:
3
L
2
3
3
3
5
ESI-TOF-MS m/z 646.0753 (calc. 646.063 for [[Zn
3 3 2
(μ-OH) L ]
of the known Zn
3
(μ-OH) species. The perchlorate anions act
3
−
−
+ 2+
(
ClO
4
)
3
− 2(ClO
4
) − OH − H ] ), 1395.0936 (calc. 1398.081 for
−
−
+ +
[[Zn (μ-OH) L ](ClO ) −ClO − OH − H ] ). IR (KBr pellet,
3
3
2
4 3
4
−1
cm ): 3541br, 2956w, 1593m, 1404m, 1255m, 1103s, 839s,
7
8
1
73m, 705m, 625m, 424m. H NMR (Me
.45 (d, J = 7.6 Hz, 3H) 8.21 (s, 3H) 8.17 (d, J = 4.1 Hz, 3H) 7.97
2
CO-d
6
, 300 MHz,δ):
3
3
3
(s, 3H) 7.60 (dd, J = 6.0, 6.0 Hz, 6H) 0.74 (s, 18H).
X-ray crystallography
X-ray data were collected using a Bruker SMART automatic
diffractometer with graphite-monochromated Mo Kα radiation
(
λ = 0.71073 Å) and a CCD detector at −25 °C. Thirty-six frames
of two-dimensional diffraction images were collected and pro-
cessed to obtain the cell parameters and orientation matrix.
The data were corrected for Lorentz and polarization effects.
The absorption effects were corrected using the multi-scan
3 3 2 4 3 3 2
Scheme 1 Synthetic scheme of [Zn (μ-OH) L ](ClO ) ·4CH CN·2H O
3
3
method (SADABS). The structures were solved using direct and photoluminescence properties for molecular recognition.
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3 3 2 4 3 3 2
Fig. 1 Crystal structures of [Zn (μ-OH) L ](ClO ) ·4CH CN·2H O.
Relevant bond lengths: Zn–O = 1.899(3)–1.930(3) Å, Zn–N = 2.023(3)–
Fig. 2 ESI-TOF-MS data on the present zinc(II) complex corresponding
to [M−ClO −OH −H ] (red line, calc.; black line, found).
4
2.032(3) Å, O–Zn–O = 102.9(1)–106.1(1)°, O–Zn–N = 103.1(1)–123.3(1)°,
−
−
+ +
N–Zn–N = 103.6(1)–109.4(1)°.
found to be consistent with their structures (see ESI Fig. S3†).
as counteranions rather than ligands. The two central phenyl
rings are nearly parallel to each other with a dihedral angle of
1
The H chemical shifts of [Zn
show up-field shift relative to L and its H NMR spectrum in
3
3 2 4 3 3 2
(μ-OH) L ](ClO ) ·4CH CN·2H O
1
3
.5(2)°, which arrangement is similar to that of our previous
3
6,37
acetone is consistent with its crystal structure. However, the
cyclophanes.
out-of-plane of the C
The pyridyl donors are directed toward the
-symmetric facial ligand, and the tilting
2
addition of Me SO to the acetone solution initiates dynamic
3
molecular behavior (10 : 2) and then, finally, dissociation
angle between the central benzene is 76.0(1)–81.8(1)°.
(
>10 : 4), as shown in Fig. 3. L, when irradiated with UV light,
Construction principle
Formation of the 6-membered hydrolyzed Zn
3
3
(μ-OH) ring can
be similarly explained by a report that is available in the litera-
35
ture. Hydrolysis is an important factor in the self-assembly
reaction and, thus, in the formation of the Zn (μ-OH) skel-
3
3
eton. But what is the critical driving force behind the for-
mation of a discrete trimetallic sandwich-type molecule rather
than coordination polymers? In the present study, the addition
of trace NaOH to the reaction system accelerated the formation
of the product. The bridged-hydroxo moiety was probably
formed through the hydrolysis of trace water molecules in the
reaction system. That is, the basic conditions for the self-
assembly accelerated the hydrolysis. A combination of the
tetrahedral geometry of zinc(II) ions and the appropriate tri-
dentate ligand seems to be a key role for the formation of a
sandwich-shaped Zn(II) complex. Specifically, the meta-posi-
tion of the N-donor might be the obstacle to the formation of
coordination polymers. Also, the size of the perchlorate
counteranion seems to partially contribute to the formation of
the discrete structure. The colorless crystalline product of
3 3 2 4 3 3 2
[Zn (μ-OH) L ](ClO ) ·4CH CN·2H O is air-sensitive and soluble
in acetone and methanol. It is dissociated in N,N-dimethyl-
formamide and dimethyl sulfoxide and insoluble in water and
chloroform. According to ESI-TOF-MS data in acetone solution,
the [Zn (μ-OH) L ](ClO ) ·4CH CN·2H O skeletons along with
3
3
2
4 3
3
2
the respective ligand species were detected (Fig. 2). In the
present study, the skeletal decomposition temperature of
[
Zn (μ-OH) L ](ClO ) ·4CH CN·2H O was about 290 °C, and the
3
3
2
4 3
3
2
1
Fig. 3 Partial H NMR spectra of [Zn
3
(μ-OH)
to Me CO-d
6
SO-d are 0 : 10 (a), 10 : 4 (b), 10 : 3 (c),
3
L
2
](ClO
4 3 3 2
) ·4CH CN·2H O
solvate acetonitrile and water molecules evaporated within a
wide 90–180 °C range (weight loss: calc. 11.8%, found 10.8%)
upon the addition of Me
volume ratios of Me CO-d
2
SO-d
6
2
6
at room temperature. The
2
6
: Me
2
(see ESI Fig. S2†). Their infrared (IR) spectra, moreover, were 10 : 2 (d), 10 : 1 (e), 10 : 0.5 (f), 10 : 0 (g).
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3 2 2 3
displays a weak emission band at λem = 373 nm (λex = 317 nm) in as CHCl , CH Cl , 1,2-dichloroethane, EtOH, CH CN, benzene,
the solid state. [Zn (μ-OH) L ](ClO ) ·4CH CN·2H O shows an toluene, and phenol (see ESI Fig. S5†), only CH I quenches
3
3
2
4 3
3
2
2 2
intense emission band at λem = 410 nm (λex = 333 nm) in metha- the emission of the complex. In order to establish the quench-
nol and an emission band at λem = 324 nm (λex = 275 nm) in the ing mechanism, the fluorescence quenching data were ana-
solid state (Fig. 4; ESI Fig. S4†). The sandwich-shaped complex’s lyzed in this study using the Stern–Volmer equation (eqn
4
1
emission shows an unusual quenching selectivity to the CH
I
2 2
(1)),
molecule in both methanol and the solid state. Thus, the emis-
sion band is blue-shifted relative to the corresponding L.
I0
¼ 1 þ KSV½Qꢀ
ð1Þ
I
where I
quencher (CH
concentration, and KSV is the Stern–Volmer constant defining
0
and I denote the emission intensity before and after
Recognition behavior via quenching
2 2
I
) addition, respectively, [Q] is the quencher
10
Recently, significant attention has been paid to d zinc(II)
the quenching efficiency. The Stern–Volmer constant KSV
=
complexes owing to their various applications in chemical
38,39
1
131.4 was evaluated from the initial linear part of the quench-
sensors, catalysts, and electroluminescent displays.
The
4
2,43
ing curve, which indicates dynamic quenching.
The fluo-
complex’s emission bands can be ascribed to the ligand-to-
metal charge transfer (LMCT) as well as the ligand’s intrinsic
characteristics. Such a significant difference between L and
the complex in intensity can be attributed to the effective
increase of the Zn–N bond rigidity and the reduction in the
rescence decays of [Zn
various CH concentrations in a methanol solution were all
fit to biexponential curves (see ESI Fig. S6†). The lifetime (τ)
shortening after the addition of CH as a quencher is due to
the dynamic quenching mechanism.
3
3 2 4 3 3 2
(μ-OH) L ](ClO ) ·4CH CN·2H O in
2 2
I
2 2
I
4
4
2
1
At higher concen-
loss of energy through radiationless decay. Although the
exact nature of the interactions between the CH I molecule
trations of the quencher, a non-linear plot of the Stern–Volmer
equation suggests the presence of a static quenching com-
ponent. The crystalline solid after several washings with
diethyl ether in order to remove CH2I2 is recyclable for
additional molecular recognition (see ESI Fig. S7†).
2
2
and the complex in either methanol or the solid state cannot
be established at this moment, the high selectivity of the
photoluminescence of the zinc(II) complex towards CH I can
2
2
be attributed to the reasonable matching between the two
species. General luminescence quenching of a metal complex
4
0
can occur in either of two ways: (1) instantaneous quenching
when a quencher CH lies within a critical radius R
2
I
2
c
contain- Conclusions
ing n molecules around the complex; (2) diffusive quenching
caused by the interaction of diffusing excited fluorophore and
quencher CH I molecules. Thus, a fraction of the complex
2 2
excited at any given moment is quenched instantaneously and
the remaining ones either undergo diffusional quenching or
spontaneous decay. Among the various small chemicals such
This communication provides a proof-of-experiment example
of a novel C -symmetric tris(silyl-pyridyl) tridentate ligand
3
facilitating the formation of a sandwich-shaped M
ture. The sandwich-shaped M Zn(II) complex has interesting
structural features, and its strong blue photo-luminescence
efficiently recognizes the CH molecule. Although the photo-
3 2
L architec-
3 2
L
2 2
I
response is still far from suitable for practical applications, the
uniquely shaped complex, based on the novel ligand, is prom-
ising as a photoluminescent sensor for specific small mole-
cules. According to the results, the fluorescence quenching
follows the dynamic quenching mechanism. These results
could provide important clues to the design of capsule-like
self-assemblies having potential catalyst, sensor, and reco-
gnition applications. Additional and more systematic studies,
for example on the synthesis and coordination frameworks of
related ligands, are in progress.
Acknowledgements
This work was supported by a National Research Foundation
of Korea (NRF) grant funded by the Korean Government
Fig. 4 Fluorescence excitation (black line) and emission (blue line)
[MEST] (2016R1A2B3009532 and 2016R1A5A1009405).
3 3 2 4 3 3 2
spectra of [Zn (μ-OH) L ](ClO ) ·4CH CN·2H O in a methanol solution
−
5
in the presence of various CH
2
−4
I
2
concentrations (0; 4.09 × 10 ; 8.15 ×
−5
; 1.22 × 10 ; 1.62 × 10 ; 2.02 × 10 ; 2.41 × 10−4; 2.80 × 10−4
;
−4
−4
1
0
−1
3
.19 × 10−4; 3.58 × 10−4; 3.97 × 10−4; 4.36 × 10−4 mol L ); inset: Stern– Notes and references
0 2 2
Volmer plots of I /I versus CH I concentration, [Q], for the complex in
methanol.
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