Synthesis, characterization and antibacterial activity of a new silver(I) complex based on a flexible dicarboxylic acid ligand

Article abstract of DOI:10.1016/j.molstruc.2015.11.021

A novel silver(I) complex sustained by a flexible dicarboxylic acid ligand, [Ag₂(L)]_n (1, H₂L = 2,2′-{[1,2-phenylenebis(methylene)]-bis(sulfanediyl)}dibenzoic acid), has been synthesized and structurally characterized. In 1, four anti conformation L^2- ligands bind three silver(I) ions to form a trinuclear subunit through S...Ag and Ag...Ag interactions, and then those trinuclear subunits are further extended to an infinite 1D silver(I) chain through the anti L^2- ligands. Thus, the thermal stability, luminescent behavior and antibacterial activity of 1 were also discussed.

Full text of DOI:10.1016/j.molstruc.2015.11.021

Accepted Manuscript
Synthesis, characterization and antibacterial activity of a new silver(I) complex based
on a flexible dicarboxylic acid ligand
Jie Sun, Qing-rong Huang, Ju-hua Zhou
PII:
S0022-2860(15)30426-9
10.1016/j.molstruc.2015.11.021
MOLSTR 21971
DOI:
Reference:
To appear in: Journal of Molecular Structure
Received Date: 2 September 2015
Revised Date: 6 November 2015
Accepted Date: 11 November 2015
Please cite this article as: J. Sun, Q.-r. Huang, J.-h. Zhou, Synthesis, characterization and antibacterial
activity of a new silver(I) complex based on a flexible dicarboxylic acid ligand, Journal of Molecular
Structure (2015), doi: 10.1016/j.molstruc.2015.11.021.
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ACCEPTED MANUSCRIPT
Graphical Abstract
Synthesis, characterization and antibacterial activity of a new silver(I)
complex based on a flexible dicarboxylic acid ligand

ACCEPTED MANUSCRIPT
Synthesis, characterization and antibacterial activity of a new silver(I)
complex based on a flexible dicarboxylic acid ligand
Jie Sun*, Qing-rong Huang, Ju-hua, Zhou
School of Life ScienceꢀLudong University, Yantai, 264025, Shandong, People’s Republic of China.
Abstract
A novel silver(I) complex sustained by a flexible dicarboxylic acid ligand, [Ag2(L)]n
(1, H2L = 2,2’-{[1,2-phenylenebis(methylene)]-bis(sulfanediyl)}dibenzoic acid), has
been synthesized and structurally characterized. In 1, four anti conformation L2-
ligands bind three silver(I) ions to form a trinuclear subunit through S···Ag and
Ag···Ag interactions, and then those trinuclear subunits are further extended to an
infinite 1D silver(I) chain through the anti L2- ligands. Thus, the thermal stability,
luminescent behavior and antibacterial activity of 1 were also discussed.
Keywords: Silver(I) chain; Flexible dicarboxylic acid ligand; Ag···Ag interaction;
Crystal structure; Antibacterial activity
1

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1. Introduction
The past decade have witnessed the boom of metal-organic coordination
complexes(MOCCs), due to their intriguing topologies and potential functional
applications in the fields of storage and separation, magnetism, catalysis,
luminescence and membrane [1-6]. As we know that much attention has been focused
on the assembly of MOCCs based on a rigid carboxylate and N-containing ligands,
however, the systemic research of flexible carboxylate ligand in the construction of
metal–organic coordination systems is somewhat rare[7]. Flexible counterparts can
transform their conformations to match the coordination requirements of the metal
centre. This can give a richer variety of structures than found for a rigid-ligand
equivalent. Among various flexible ligands, multicarboxylates containing –CH2–O–
or –CH2–S– arms have attracted great interests[8]. Recently, Sun’s group have
reported four metal–organic complexes based on three flexible dicarboxylic acid
ligands and copper paddlewheel SBU[9], our group have also reported a mononuclear
copper
complex
Cu(NH3)3(L6)]·(H2O)0.66
(1)
(H2L6
=
2,2’-(1,2-phenylenebis(methylene))bis(sulfanediyl)-dibenzoic acid) and the complex
could be dimerized to form a binuclear complex with an altered copper coordination
geometry through thermal SCSC transformation or solid state reaction under dry
grinding conditions[10].
On the other hand, compared to wildly used Zn, Cd, Cu transition and rare earth
element during construction of MOCCs, silver-centered metal-organic coordination
systems are also rarely investigated. Silver-containing complex appeared as
antimicrobial agents since the middle age[11]. Because of their multi-targeting
mechanism, silver-based antimicrobial agents are often applied to overcome bacterial
resistance[12]. Silver(I) has shown to be able to inactivate proteins, bind to thiol
groups and form stable Ag–S bonds. Silver ions are also able to change the structure
of the bacteria cell wall, leading to changes in its mobility and stability and to a
subsequent bacterial death, the mechanisms of action and resistance of silver ions
have been intensively study by recent reviews[13]. It is reported that silver-centred
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complexes show higher antibacterial activity than silver ions, because of their
synergistic effects between silver ions and organic ligands. Based on the
considerations above, herein we reported a silver(I) complex based on a flexible
dicarboxylic acid ligand(H2L), and studied the photo- and biological properties of
final complex.
[Please insert: Scheme1 The synthesis procedures of the H2L in complex 1]
2. Experimental procedure
2.1. Materials and methods
All the reagents and solvents employed were commercially available and used as
received without further purification. H2L was synthesized according to the procedure
of Dai et al[9]. Infrared spectra were recorded on a Bruker VERTEX-70 spectrometer
as KBr pellets in the frequency range 4000-400 cm-1. The elemental analyses (C, H
contents) were determined on
a
CE instruments EA 1110 analyzer.
Photoluminescence measurements were performed on a Hitachi F-7000 fluorescence
spectrophotometer with solid powder on a 1 cm quartz round plate with a dewar flask
apparatus. TG curves were measured from 30 to 600 °C on a SDT Q600 instrument at
a heating rate 10 °C/min under the N2 atmosphere (100 mL/min).
2.2. Synthesis of [Ag2(L)]n
Three drops of NaOH (0.1 mL, 0.8M) was added to a suspension of H2L (0.015 g,
0.037 mmol) in H2O (1 mL) to give a clear solution. AgNO3 (0.030 g, 0.170 mmol) in
MeOH (9 mL) was added to the clear solution, upon which lots of brown precipitate
formed immediately. After three drops of NH3·H2O (0.1 mL, 25–28%) was added, a
colorless solution was generated after 10 minutes stirring, which was filtered and
transferred to a test tube. After slow evaporation at room temperature for two months,
large stick colorless crystals of 1 were formed (yield: 45%). Elemental analysis calcd
(%) for 1: C 42.30, H 2.56, N 10.25; found: C 42.02, H 2.52, N 10.11%. Selected IR
peaks (cm-1): 3395 (m), 2963 (m), 1590 (s), 1546 (s), 1399 (s), 1361 (m), 854 (w), 788
(m), 725 (w), 713 (m).
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2.3. X-ray crystallography
Single crystals of the complex 1 was collected on a SuperNova diffractometer
equipped with a molybdenum micro-focus X-ray source (λ = 0.71073 Å) and an Eos
CCD detector under 293 K. The data were collected with a ω-scan technique and an
arbitrary φ-angle. Data reduction was performed with the CrysAlisPro package, [14]
and an analytical adsorption correction was performed. The structures were solved by
direct methods and refined by full-matrix least-squares on F2 with anisotropic
displacement using the SHELXTL software package. [15] The non-H atoms were
treated anisotropically, whereas the aromatic and hydroxy hydrogen atoms were
placed in calculated, ideal positions and refined as riding on their respective carbon or
oxygen atoms. The structures were examined using the Addsym subroutine of
PLATON [16] to assure that no additional symmetry could be applied to the models.
For 1, crystal data and collection and parameters are summarized in Table 1, and
selected bond lengths and angles are given in Table 2.
[Insert Table 1 and 2 here]
Table 1. Crystallographic data for 1
Table 2. Selected bond lengths and angles for 1
3. Results and discussion
3.1. Crystal structure of [Ag2(L)]n 1.
The molecular structure of 1 was determined by single-crystal X-ray diffraction
analysis. Complex 1 crystallizes in monoclinic space group of C2/c and the
asymmetric unit contains one independent and two halves Ag ions, and one H2L
ligand. As shown in Fig. 1, when the Ag⋯Ag interactions are not taken into account,
the coordination number of three Ag are all four, but they adopt three different
coordination environments, indicating the rich coordination mode of Ag. Ag1 in
complex 1 adopt four-coordinated tetrahedral geometry, completed by four O atoms
from four different H2L ligands; Ag2 is bonded to two O, two S atoms of three H2L
ligands, and Ag2 atom forming distorted tetrahedral geometry; the Ag3 is located in a
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square geometry and coordinated by four O atoms from three different H2L ligands.
The Ag-O bond lengths range from 2.238(3) to 2.501(2) Å and the maximum bond
angle is 119.91(9)o and the Ag-S bond lengths are located in 2.5333(8) to 2.9161(8) Å.
Both the Ag-S and Ag-O bond lengths fall in the normal ranges as the reported
complexes [17-20]. As depicted in Fig.2, the H2L ligand in 1 has an anti
conformation, as shown by the distribution of the two substituted 2-mercaptobenzoate
groups with respect to the plane of the central aromatic ring. The anti L2- ligands bind
to seven Ag(I) centres, the planes of the aromatic rings of the 2-mercaptobenzoate
arms make dihedral angles of 84.8 (3) and 77.8 (3)o. The dihedral angles between the
carboxylic groups and adjacent phenyl ring planes for one crystallographic
independent L2- ligands are ca. 5.59 and 54.58°, respectively. The neighboring
subunits were further to an infinite zigzag chain (Fig. 3) through Ag···Ag interactions
(Ag1···Ag2i = 3.2769(2), Ag1···Ag3 = 3.4258(3) and Ag2ii···Ag3= 3.8754(2) Å) and
Ag···S interactions(Ag2···S1 = 2.533(8), Ag2···S2ii = 2.5428(8) and Ag3···S1 =
2.9161(8) Å). [ symmetry code: (i) 1-x, 2-y, 1-z; (ii) 1-x, y, 0.5-z; (iii) x, 2-y, 0.5+z;
(iv) 1-x, y, 1.5-z]
[Please insert: Figure 1. The coordination environment around Ag(I) ions in 1, all
hydrogen atoms are omitted for clarity and Ag···Ag interactions highlighted by purple
dashed lines][ symmetry code: (i) 1-x, y, 0.5-z; (ii) 1-x, 2-y, 1-z].
[Please insert: Figure 2. The coordination environment H2L ligand in 1, all hydrogen
atoms are omitted for clarity and Ag···Ag interactions highlighted by purple dashed
lines] [ symmetry code: (i) 1-x, 2-y, 1-z; (ii) 1-x, y, 0.5-z; (iii) x, 2-y, 0.5+z; (iv) 1-x, y,
1.5-z].
[Please insert: Figure 3. The 1D chain structure of 1 supported by Ag···Ag and
Ag···S interactions]
In complex 1, the silver chains are aligned parallel to one another in the
crystalline phase. There are abundant secondary interactions between adjacent silver
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wires(Fig.4).
[Please insert: Figure 4. The packing structure of 1 view along (a) a and (b) c
direction]
3.2. X-ray Power Diffraction Analyses and Thermogravimetric Analyses.
Phase purity of 1 is sustained by the X-ray powder diffraction pattern (Fig.
S1). The dissimilarities in intensity may be due to the preferred orientation of the
crystalline powder samples. The solid FT-IR spectrum (Fig. S2) of 1 shows that
the asymmetric and symmetric stretching vibrations of deprotonated carboxyl
group are in ~1592 and ~1388 cm-1, respectively [21-23]. These results are in good
agreement with solid state crystal structure. To study the thermal stablity of
complex 1, the thermal gravimetric analyse (TGA) of 1 was measured from 40 to
800 °C at a heating rate 10 °C/min under the N2 atmosphere. As shown in Fig. S3,
the frame of complex 1 shows high thermal stability and almost no weight loss was
observed until 248 °C, after that, the frame of complex 1 began to decompose,
accompanying the release of the H2L ligand.
[Please insert: Figure 5. The photoluminescence of free ligands and complex 1 in
solid state]
3.3. Photoluminescence Properties.
The photoluminescence of H2L and complex 1 were measured in solid state at
room temperature (Fig. 5). The free ligand H2L displays photoluminescence with
emission maximum at 416 nm (λex = 330 nm). It can be presumed that this emission
peak originates from the π→π* transition. For complex 1, at room temperature it
displays an emission band at 438 nm, upon excitation at 330 nm. Compared with the
emission of free H2L ligand, the emission band of 1 is red-shifted by 22 nm, which
may contribute to ligand-to-metal charge transfer (LMCT) transition perturbed by
Ag···Ag interactions from the electronic transition between coordinated O atoms p
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orbitals and Ag(I) ion 5s orbital[24-25].
3.4. Antibacterial Activity.
The method of Oxford-cup tests were used to evaluated the antibacterial activity
of AgNO3, H2L and complex 1. The antibacterial activity was estimated by
monitoring the growth of certain Gram-positive (B. subtilis, S. aureus) and
Gram-negative (E. coli) bacterial strains in the presence of different concentrations of
these complexes ranging from 1, 5 and 10 mg·mL−1. As presented in Table S1, it
showed the results of in vitro activity determination based on the diameter of the
inhibition zone (in mm). H2L did not show antibacterial activity, however, complex 1
and AgNO3 have some antibacterial activity to three model bacterial strains, which
means that the antibacterial activity have relations with silver ions. As shown in Fig.6,
with the increasing of complex 1 and AgNO3 content of antibacterial activity
increased. Complex 1 resulted to have bigger antibacterial activity to E. coli bacterial
strains than the original compound (H2L) and AgNO3 solutions, the diameter of the
inhibition zone is 28 mm when the concentration of complex 1 is up to 10 mg·mL−1.
These results suggested that the combination of H2L with the silver(I) may represent
an additional advantage for its use in the management of infections caused by S.
aureus, B. subtilis and especially E. coli.
[Please insert: Figure 6. The antibacterial activity of complex 1 against B.
subtilis(a), S. aureus(b) and E. coli(c) ]
4. Conclusions
In summary, we utilized the flexible dicarboxylic acid ligand to synthesize and
characterize a novel 1D silver chain sustained by Ag···Ag and Ag···S interactions.
The thermal stability, photoluminescence behavior and antibacterial activity of 1 were
also discussed. Compare with free ligand and silver, complex 1 shows higher
antibacterial activity against E. coli.
Acknowledgments
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This work was financially supported by the National Natural Science Foundation
of China (No. 21401096).
Appendix A. Supplementary material
CCDC 1035701 contains the supplementary crystallographic data for this paper.
These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/
retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB 21EZ, UK; fax: (+44) 1223-336-033; or e-mail:
deposit@ccdc.cam.ac.uk. Supplementary data associated with this article can be
found, in the online version.
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TableÅ1ÅCrystalÅdataÅandÅstructureÅrefinementÅforÅcomplexÅ1.Å
IdentificationÅcodeÅ
EmpiricalÅformulaÅ
FormulaÅweightÅ
Temperature/KÅ
CrystalÅsystemÅ
SpaceÅgroupÅ
a/ꢀÅ
complexÅ1Å
C22H16Ag2O4S2Å
624.21Å
273.15Å
monoclinicÅ
C2/cÅ
20.2580(16)Å
15.6777(13)Å
13.6916(11)Å
90.00Å
b/ꢀÅ
c/ꢀÅ
α/°Å
β/°Å
106.7530(10)Å
90.00Å
γ/°Å
Volume/ꢀ3Å
4163.9(6)Å
8Å
ZÅ
ρcalcg/cm3Å
μ/mm-1Å
1.991Å
2.109Å
F(000)Å
2448.0Å
CrystalÅsize/mm3Å
RadiationÅ
2ΘÅrangeÅforÅdataÅ
collection/°Å
0.2Å×Å0.13Å×Å0.11Å
MoKαÅ(λÅ=Å0.71000)Å
4.96ÅtoÅ55.1Å
-25ÅꢁÅhÅꢁÅ26,Å-20ÅꢁÅkÅꢁÅ20,Å-17ÅꢁÅlÅꢁÅ
IndexÅrangesÅ
17Å
ReflectionsÅcollectedÅ
IndependentÅreflectionsÅ
17457Å
4806Å[RintÅ =Å0.0276,ÅRsigmaÅ =Å0.0280]Å
Data/restraints/parametersÅ 4806/0/273Å
Goodness-of-fitÅonÅF2Å
1.021Å
FinalÅRÅindexesÅ[I>=2σÅ(I)]ÅR1Å =Å0.0317,ÅwR2Å =Å0.0664Å
FinalÅRÅindexesÅ[allÅdata]Å R1Å =Å0.0453,ÅwR2Å =Å0.0716Å
LargestÅdiff.Åpeak/holeÅ/ÅeÅꢀ-3Å0.65/-0.60Å
(2) Table 2 Selected bond distances (Å) and angles (°) for 1
Ag1—O1
Ag1—O1i
Ag1—O3ii
Ag1—O3iii
Ag2—S1
Ag2—S2ii
2.393 (2)
2.393 (2)
2.238 (3)
2.238 (3)
2.5333 (8)
2.5428 (8)
Ag2—O2i
Ag3—S1
2.280 (2)
2.9161 (8)
2.9161 (8)
2.501(2)
2.501(2)
2.244(2)
Ag3—S1iii
Ag3—O1
Ag3—O1iii
Ag3—O1iv

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O1i—Ag1—O1
O3iii—Ag1—O1i
O3iii—Ag1—O1
S1—Ag2—S2ii
O2i—Ag2—S2ii
O4ii—Ag3—O1
O4iv—Ag3—O1
82.18 (10)
106.65 (9)
106.65 (9)
135.84 (3)
101.21 (8)
97.89 (9)
82.11 (9)
O3iii—Ag1—O1
O3iii—Ag1—O1i
O3ii—Ag1—O3iii
O2i—Ag2—S1
119.91 (9)
119.91 (9)
117.22 (18)
120.02 (9)
180.0
S1—Ag3—S1iii
O4iv—Ag3—O1iii
O4ii—Ag3—O4iv
97.89 (9)
180.000 (1)
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y+2, z−1/2; (iii) −x+1, −y+2, −z+1; (iv)
−x+1, y, −z+3/2; (v) x, −y+2, z+1/2.

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Scheme1 The synthesis procedures of the H2L in complex 1

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Figure 1. The coordination environment around Ag(I) ions in 1, all hydrogen
atoms are omitted for clarity and Ag···Ag interactions highlighted by purple
dashed lines][ symmetry code: (i) 1-x, y, 0.5-z; (ii) 1-x, 2-y, 1-z].

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Figure 2. The coordination environment H2L ligand in 1, all hydrogen atoms are
omitted for clarity and Ag···Ag interactions highlighted by purple dashed lines]
[ symmetry code: (i) 1-x, 2-y, 1-z; (ii) 1-x, y, 0.5-z; (iii) x, 2-y, 0.5+z; (iv) 1-x, y,
1.5-z]

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Figure 3. The 1D chain structure of 1 supported by Ag···Ag and Ag···S
interactions

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Figure 4. The packing structure of 1 view along (a) a and (b) c direction

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[Please insert: Figure 5. The photoluminescence of free ligands and complex 1 in
solid state]

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[Please insert: Figure 6. The antibacterial activity of complex 1 against B.
subtilis(a), S. aureus(b) and E. coli(c) ]

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Reserach Highlights
Title: Synthesis, characterization and antibacterial activity of a new silver(I)
complex based on a flexible dicarboxylic acid ligand
Authors: Jie Sun*, Qingrong, Huang, Juhua, Zhou
(i)
A novel silver(I) complex sustained by a flexible dicarboxylic acid ligand has
been synthesized and structurally characterized.
(ii)
The silver(I) wire was sustained by S···Ag and Ag···Ag interactions.
(iii) Compare with free ligand and silver, complex 1 shows higher antibacterial
activity against E. coli