Coordination polymers of indole based bis-ligand: Thermal, spectral, and antimicrobial aspects

Article abstract of DOI:10.1080/15533174.2010.522882

A few coordination polymers of Cu(II), Zn(II), Mn(II), Co(II), and Ni(II), obtained from the reaction of metal acetate with newly synthesized ligand, namely [(5,5'-(3, 3'-((4-nitrophenyl)methylene)-bis-(¹H-indole-3,1- diyl)-bis-(methylene)diqui

Full text of DOI:10.1080/15533174.2010.522882

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Coordination Polymers of Indole Based Bis-ligand:
Thermal, Spectral, and Antimicrobial Aspects
Hasmukh S. Patel a & Darshana J. Patel a
a Department of Chemistry , Sardar Patel University Gujarat , India
Published online: 02 Feb 2011.
To cite this article: Hasmukh S. Patel & Darshana J. Patel (2011) Coordination Polymers of Indole Based Bis-ligand:
Thermal, Spectral, and Antimicrobial Aspects, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal
Chemistry, 41:1, 72-80
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 41:72–80, 2011
Copyright © Taylor & Francis Group, LLC
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2010.522882
Coordination Polymers of Indole Based Bis-ligand: Thermal,
Spectral, and Antimicrobial Aspects
Hasmukh S. Patel and Darshana J. Patel
Department of Chemistry, Sardar Patel University Gujarat, India
Several coordination polymers of bis-ligands based
on 5-chloromethyl-8-hydroxyquinoline (CMQ) have been
reported.[11,12] Ion-exchange resins and amino or hydroxyl func-
tionalized polymers have also been prepared from CMQ.[13,14]
The formation of coordination polymers with ligands having
enhanced chelating ability, such as a bidentate 8-HQ moiety,
in which two 8-hydroxyquinolinyl end groups are joined a
linear aliphatic bridge, usually at the 5,5ꢀ-position, has been
reported.[12] Looking to the easy derivatization of CMQ, it was
thought worthwhile to have a ligand containing both indole and
8-HQ moieties together. If CMQ is reacted with bis-indole, the
compound formed will have not only metal bonding potential,
but also good biological activity due to the presence of the in-
dole and 8-HQ moieties.[15,16] The present study describes the
synthesis and characterization of a novel bis-ligand and its co-
ordination polymers with Cu2+, Zn2+, Mn2+, Co2+, and Ni2+
metal ions. The synthetic routes to the preparation of ligand and
coordination polymers are shown in Scheme 1.
A few coordination polymers of Cu(II), Zn(II), Mn(II),
Co(II), and Ni(II), obtained from the reaction of metal
acetate with newly synthesized ligand, namely [(5,5ꢀ-(3,
3ꢀ-((4-nitrophenyl)methylene)-bis-(1H–indole–3,1–diyl)-bis-
(methylene)diquinolin-8-ol)] (NIMQ), are described here. The
ligand has been characterized by elemental analysis, 1H-NMR,
and 13C-NMR spectra and thermogravimetric analysis. Elemental
analysis, infrared and electronic reflectance spectra, magnetic
susceptibility measurements, and thermogravimetry have been
employed to characterize the coordination polymers. Magnetic
moment and reflectance spectral studies reveal that a distorted
octahedral geometry has been assigned to all the prepared coordi-
nation polymers. The microbicidal activity of all the samples has
also been monitored against plant pathogens.
Keywords antimicrobial activity, coordination polymers, magnetic
moment, spectral studies, thermogravimetric analysis
INTRODUCTION
Much research is being directed towards the preparation of
a polymeric chain by the formation of metallic chelates. Some
success has been achieved in the preparation of coordination
polymers from bi-functional ligand. An efficient method for
synthesizing this type of polymer is by introducing an inorganic
component either chemically bonded or as filler.
Coordination polymers based on 8-hydroxyquinoline (8-
HQ) and its derivatives have received attention due to their ap-
plications in various areas such as in wastewater treatment for
metal recovery, in proactive coatings, as an in vitro and in vivo
anticarcinogenic agent, and for potential biological activity.[1−8]
In addition, fluorescence enhancement occurs by cation binding
as in metal chelates of 8-HQ, which exhibited intense fluores-
cence activity.[9,10]
EXPERIMENTAL
Materials
All chemicals used were of analytical grade.
Synthesis of Ligand (NIMQ)
The
precursors
5-chloromethyl-8-hydroxyquinoline
hydrochloride and 3,3ꢀ–(4-nitrophenylmethanediyl)-bis-(1H-
indole) (BI) were prepared following known methods.[17−19]
NIMQ was formed when a mixture of 5-chloromethyl-
8-hydroxyquinoline hydrochloride (23 g, 0.1 mole) and
bis-indole (32.2 g, 0.1 mole) was refluxed in acetone for
2.5 h with occasional stirring. The resulting solution was
then made alkaline with dilute ammonia to precipitate out
the ligand NIMQ, which was then filtered and air dried. The
yield of NIMQ was 70% and its melting point was 236–238◦C
(uncorrected).
Received 30 June 2010; accepted 27 July 2010.
One of the authors, D. J. Patel, is thankful to UGC (New Delhi) for
awarding meritorious scholarship.
Address correspondence to Hasmukh S. Patel, Department of
Chemistry, Sardar Patel University, Vallabh Vidyanagar–388120,
Gujarat, India. E-mail: drhspatel786@yahoo.com
Preparation of Coordination Polymers
All coordination polymers were synthesized using metal ac-
etates by the method described below.
72

INDOLE BASED BIS-LIGAND
73
CH2Cl
OH
Magnetic susceptibility measurements of the coordination
polymers were carried out at room temperature using the Gouy
method reported in literature,[21] and their data are given in
Table 1. Mercury tetrathiocynato cobaltate (II) was used as a cal-
ibrant. Molar susceptibilities were corrected for diamagnetism
of the component atoms using Pascal’s constant. Thermogravi-
metric analysis (TGA) of the coordination polymers was carried
out on a DuPont 950 TGA analyzer in air at a heating rate of
10◦C/min.
C6H4NO2
H
+
2
N
H
N
H Cl
_
N
H
+
Bis-Indole
5-chloro-methyl 8-hydroxyquinoline
(CMQ)
Acetone NaHCO3
- 4HCl
C6H4NO2
H
N
N
CH2
CH2
Preparation of the Microbial Culture
The antimicrobial activity of the ligand and its coordina-
tion polymers was investigated against bacterial strains of Es-
cherichia coli, Bacillus subtillis, Staphylococcus aureus, and a
yeast strain of Saccharomyces cerevisiae by standard micro-
biological parameters using the agar diffusion method.[22] The
concentration of the compounds tested for the antimicrobial ac-
tivity was 500 ppm. The bacterial culture was maintained on
N-agar (N-broth, 2.5% w/v agar). The yeast culture was main-
tained on MGYP in 3% (w/v) agar.
For inoculum developments of bacterial and yeast culture,
a loop of cell mass from pregrown slants was inoculated into
sterile N-broth tubes containing 15 mL of medium and incubated
on a shaker at 150 rpm and 40◦C for 24h to obtain sufficient
cell density (i.e., 1×108 cells/mL). Sterilized melted soft N-
agar (1% in distilled water, 10.0 mL) was cooled to 40◦C and
inoculated with 0.1 mL suspension of the test culture, mixed
thoroughly, poured in the Petri dish containing sterilized N-agar
medium, and allowed to solidify.
N
N
OH
NIMQ
OH
-2H+
M+2
OH2
M
OH2
N
N
M
O
CH2
H2C
O
N
N
n
OH2
OH2
C6H4NO2
[MNIMQ(H2O)2]n
Where, M = Cu(II), Ni(II), Co(II), Mn(II), and Zn(II)
SCH. 1. The synthetic route for the coordination polymers.
A warm and clear solution of NIMQ (0.01 mol) in 20%
aqueous formic acid was added to a solution of copper acetate
(0.01 mol) in 50% aqueous formic acid with constant stirring.
After complete addition of the metal salt solution, the pH of
the reaction mixture was adjusted (∼5) with dilute ammonia
solution. The coordination polymers thus separated out in the
form of a suspension was digested on a water bath for 1 h. The
solid polymer was filtered, washed with hot water followed by
acetone and dimethyl formamide (DMF), and then dried in air
at room temperature. The yields of all coordination polymers
were almost quantitative. The formula of coordination polymers
is shown below.
Two cups were prepared with the help of a sterile cup-borer
on opposite ends. One was filled with 0.1 mL of test sample and
the other with 0.1 mL of DMSO solvent as a control. To find
the minimum inhibitory concentration (MIC), all the cultures
were tested for different concentrations of compound ranging
from 50–1000 ppm. Thereafter, the plates were transferred to
the refrigerator for 10 min to allow the sample diffuse out from
the ditch and into the agar before the organism start growing.
This is followed by incubation at 40◦C for 24h. The next day,
the distance in millimeter (mm) from the ditch was measured as
a parameter of inhibition.
Media Composition
For the growth and testing of the bacteria and yeast, N-broth
and MGYP media were used. The composition for the N-broth
was peptane 0.6% (6.0 g), NaCl 0.15% (1.5 g) and beef extract
0.15% (1.5 g) dissolved in distilled water (1-L) and pH was
adjusted to 6.7–7.3; for MGYP, it was malt extract (3.0 g),
glucose (10.0 g), teats extract (3.0 g) and peptones (5.0 g),
dissolved in distilled water (1 L) and the pH was adjusted to 5.5.
Analytical Procedures
Elemental analyses for C, H and N of ligand NIMQ and its co-
ordination polymers were carried out on a Thermofingan Flash
1101EA (Italy) (Table 1). The metal content of the coordina-
tion polymers was obtained by decomposing a weighed amount
of the material followed by complexometric titration with dis-
odium ethylene diamine tetraacetate.[20] Infrared (IR) spectra
of all the samples in KBr pellets were scanned on a Nicolet-
760 FTIR spectrophotometer. The H and 13C NMR spectrum
1
RESULTS AND DISCUSSION
of NIMQ was recorded in dimethylsulfoxide (DMSO-d6) with
tetramethylsilane as internal standard on Brucker spectrometer
(400 MHz).
Elemental analysis, colors, yield, melting points, and mag-
netic moments are summarized in Table 1. The elemental
analysis of ligand NIMQ and its coordination polymers are in

74

INDOLE BASED BIS-LIGAND
75
FIG. 1. FTIR spectrum of ligand (NIMQ).
agreement with proposed structures. All of the coordination is assigned to OH-bending of the phenolic moiety, which is ab-
polymers exhibited 1:1 metal to ligand stoichiometry. The struc- sent in the coordination polymers shown in Figure 2. The bands
ture of NIMQ and its coordination polymers are consistent at 1480 and 1588 cm−1 are due to breathing vibrations in aro-
with the FTIR, elemental analysis, 1H-NMR and 13C-NMR, re- matic ring of ligand.[11] In addition to these bands, the spectrum
flectance spectra, and TGA. The geometry of the central metal of NIMQ has many characteristic absorption bands that are iden-
ion was confirmed by reflectance spectra (UV- visible) and mag- tical to those that occur in 5,5ꢀ-methylene(8-hydroxyquinoline)
netic susceptibility measurements. Elemental analysis, physical (MBQ) and bis-indole.[18,19]
properties, and infrared data provided good evidence that the
The IR spectrum of NIMQ shows a peak at 1600 cm−1
chelates are polymeric in nature.[10,11] The suggested structure assigned to υ(C=N). On complexation, this peak shifted to
of the coordination polymers is shown in Scheme 1.
lower frequencies at 1593 cm−1 due to coordination polymer
formation.[12,23] The new bands observed in the region 470–
450 cm−1 and 420 cm−1 are probably due to the formation of
M O and M N bonds, respectively.[24] It is thus believed that
the oxygen and nitrogen atom of 8-hydroxyquinoline group are
coordinated to the metal.[25,26] From the above data, the follow-
ing structure has been proposed for the coordination polymers
shown in Scheme 1.
IR Spectra
The spectrum of ligand (NIMQ) (Figure1) shows a broad
band at 3330 cm−1 due to –OH stretching vibrations. Weak
bands at 2932 cm−1 and 2850 cm−1 are attributed to asymmet-
ric and symmetric stretching vibrations of methylene groups.
The C=N stretching in the ligand is possibly distributed at the
absorptions 1703 and 1600 cm−1. On complexation, both these
peaks show red shift, indicating bonding of nitrogen to the metal.
The C O stretching in the ligand may be traced to the absorp-
tions at 1360 and 1245 cm−1. In the complexes, these peaks are
shifted to 1342 and 1240 cm−1, respectively. This indicates the
formation of C O M bond. The peak at 1227 cm−1 in the ligand
1H NMR and 13C NMR Spectra of the Ligands (NIMQ)
The 1H-NMR spectrum of NIMQ (Figure 3) shows a signal
at δ = 4.69 ppm (s, 4H), which is assigned to two CH2-
protons. Signal at δ = 6.03 ppm (s, 1H) is assigned to aliphatic
CH proton. The signals at δ = 6.87–9.67 ppm (complex, 24H)

76
H. S. PATEL AND D. J. PATEL
FIG. 2. FTIR spectrum of Cu+2 coordination polymer.
FIG. 3. The 1H NMR spectrum of ligand (NIMQ).

INDOLE BASED BIS-LIGAND
77
TABLE 2
TGA of ligand (NIMQ) and its coordination polymers
% Weight loss at different temperature (◦C)
Activation energy(Ea)
Kcal/mol−1
Ligand/ coordination polymers
100
200
300
400
500
600
700
NIMQ
1.6
1.2
5.9
4.9
3.9
4.3
7.0
8.2
7.1
8.8
6.5
7.7
40.6
11.7
13.0
13.8
12.0
17.8
57.2
26.5
26.5
24.8
22.8
34.1
60.6
30.5
38.1
39.4
31.6
42.1
63.3
33.5
43.4
42.5
34.8
49.3
66.1
37.2
50.2
49.6
36.4
52.4
9.6
6.6
8.4
8.5
8.2
9.2
[Cu NIMQ(H2O)2]n
[NiNIMQ(H2O)2]n
[CoNIMQ (H2O)2]n
[ZnNIMQ(H2O)2]n
[MnNIMQ(H2O)2]n
3
3
are assigned to aromatic protons of quinolone, indole, and p-
nitrophenyl moieties. A sharp signal at δ = 10.94 ppm (s, 2H) is
assigned to two aromatic hydroxyl protons which are confirmed
by D2O exchange experiment.
In the CMR spectrum of NIMQ shows a signal at δ =
31.1 ppm is assigned to two CH2- carbons. Signal at δ = 32.9
ppm is assigned to CH carbon and the signals observed be-
tween δ = 111.0–153.6 ppm were assigned to aromatic carbons
of the ligand (NIMQ).
and A2g → T1g(P) transition, respectively, in an octahedral
geometry.
The reflectance spectrum of Co(II) coordination polymer
shows three absorption bands at 9,200, 18,018, and 19,000
cm−1 assignable to T1g(F) → T2g, T1g(F) → A2g and
4
4
4
4
4T1g(F) → T2g(P) transitions, respectively, of an octahedral
4
geometry.[29] The reflectance spectrum of the Mn(II) coordina-
tion polymer shows weak bands at 14,614, 19,995, and 25,600
cm−1 assignable to the A1g → T1g(4G), A1g → T2g(4G),
6
4
6
4
and 6A1g → A1g, 4Eg transitions, respectively, in an octahedral
4
environment around the Mn(II) ion.[30] The magnetic moment
value of an Mn(II) coordination polymer was 5.9 B.M., due
to a high spin d5-system with an octahedral geometry.[27] The
Zn(II) coordination polymer is not well resolved, and hence not
interpreted, but its µeff value shows that it is diamagnetic as
expected.
Electronic Spectra and Magnetic Measurements
The information regarding geometry of the coordination
polymers were obtained from their diffused reflectance spec-
tra and magnetic moment values.
The diffused reflectance spectrum of the Cu(II) coordination
polymer is shown in Figure 4, a broad band at 15,450 cm−1 due
2
to 2Eg → T2g transition,[26] while the other band observed at
22,791 cm−1 may be due to LMCT band.[24] Magnetic mo-
ment is 1.87 B.M., which is comparable to the approximate
spin only value (1.73 B.M.) expected for an unpaired electron.
The reflectance spectra and magnetic measurement data sug-
gest that the Cu(II) coordination polymer has distorted octahe-
dral geometry.[27−28] The observed magnetic moments 3.3 and
3.8 B.M., respectively, for the Co(II) and Ni(II) coordination
polymers are within the range for octahedral geometry. The re-
flectance spectra of the Ni(II) coordination polymer exhibit two
Thermogravimetric Analyses
The thermal behavior of coordination polymers and parent
bis-ligand was investigated by TGA. The TGA results of all
the samples are presented in Table 2, and their thermograms
are shown in Figure 5. The weight loss of the polymer samples
at different temperature indicates that the degradation of the
polymers is noticeable only beyond 300◦C. A very slight weight
loss (1.5 to 5%) seen from the thermogram in the temperature
3
bands at 15,603 and 22,990 cm−1 assignable to 3A2g → T1g(F)
FIG. 4. The reflectance spectrum of [CuNIMQ(H2O)2].
FIG. 5. The thermogram of ligand(NIMQ) and Cu+2 coordination polymer.

78
H. S. PATEL AND D. J. PATEL
TABLE 3
Antimicrobial activity data of the ligand (NIMQ) and its
coordination polymers
Zone of inhibitiona (mm)
Ligand/coordination
polymers
E.
B.
S.
S.
coli substilis aureus cerevisiae
NIMQ
–
–
–
14
21
23
19
22
20
–
[Cu NIMQ(H2O)2]n
[NiNIMQ(H2O)2]n
[CoNIMQ (H2O)2]n
[MnNIMQ(H2O)2]n
[ZnNIMQ(H2O)2]n
DMSOb
16
17
15
18
14
–
23
24
20
18
19
–
21
19
23
20
19
–
FIG. 6. Freeman-Carroll plot for thermal degradation of [CuNIMQ(H2O)2]n.
a16–23 mm = significantly active; 10–15 mm = moderately active;
<10 mm = weakly active.
range 50–150◦C for the parent ligand is attributed to loosely
bonded water. However, the initial gradual weight loss occurring
below 150◦C in all of the coordination polymers is traced to the
removal of loosely bonded water molecules.
The thermograms of all coordinated polymer samples
showed appreciable weight loss (6 to 12%) in the range 150
to 280◦C, which might be due to removal of coordinated water
molecules.[12,31] The rate of degradation becomes maximum at
temperature between 400◦C to 500◦C; up to this temperature
coordination polymers are most stable, each coordination poly-
mers loses about 55% of its weight when heated up to 700◦C
and thus form metal oxides.[25]
The thermodynamic activation parameter of the decompo-
sition process of the coordination polymers such as energy of
activation (Ea) and order of reaction (n), were evaluated graph-
ically by employing the Freeman–Carroll method[32] using the
following relation:
bSolvent (negative control).
Antimicrobial Activity of Ligand and its Coordination
Polymers
The antimicrobial activity of ligand (NIMQ) and its coordi-
nation polymers was studied against standard bacterial strains
of Escherichia coli, Bacillus subtillis, Staphylococcus aureus,
and yeast strain of Saccharomyces cerevisiae.
The compounds were tested at different concentration rang-
ing from 50 to 1,000 ppm to find out the minimum concentration
of the bis-ligand and polychelates, which inhibits the microbial
growth. The minimum concentration was to be found. The inhi-
bition of growth from ditch was measured in millimeter (mm),
and the results shows that all metal complexes exhibit antimi-
crobial activity against one or more strain (Table 3).
The ligand was found biologically active, and their poly-
chelates showed significantly enhanced antibacterial activity
against one or more bacterial species compared to the uncom-
plexed ligand. It is known that chelation tends to make the lig-
and a more potent bactericidal agent. The antimicrobial activity
of the compounds increases after chelation. Chelation reduces
the polarity of the metal ion by partial sharing of its positive
charge with the donor groups,[36] increasing lipophilic nature
of the central metal ion, which in turn favors its permeation to
the lipid layer of the bacterial membrane. Generally it is sug-
gested that the chelated complexes deactivate various cellular
enzymes, which play a vital role in various metabolic pathways
of these microorganism. Other factors, viz., stability constant,
molar conductivity, solubility and magnetic moment, are also
responsible for the increase in the anti-microbial activity of the
complexes.[37]
[(−Ea / 2.303R)ꢀ(1 / T)]ꢀ log Wr = −n + ꢀ log(dW / dt)
×ꢀ log Wr
where T is the temperature in K, R is gas constant, Wr = Wc-W;
Wc is the weight loss at the completion of the reaction, and W
is the total mass loss up to time t. Ea and n are the energy of
activation and order of reaction, respectively. A typical curve
of [ꢀlog (dw/dt)/ꢀlog wr] vs [ꢀ (1/T)/ꢀlogwr] for the Co(II)
coordination polymer is shown in Figure 6. The slope of the plot
gave the value of Ea/2.303R and the order of reaction (n) was
determined from the intercept.
The kinetic parameter, especially activation energy (Ea) is
helpful in assigning the strength of the coordination polymers.
The relatively high value of Ea (Table 2) indicates that the ligand
is strongly bonded to the metal ion.[33,34] Based on the activation
energy values, the thermal stability of the coordination polymers
in the decreasing order is: Mn> Co> Ni > Zn> Cu.[35]
Comparative analysis for antibacterial study of ligand and its
coordination polymers is shown in Figure 7. It is observed that
some of the polychelates were more potent bactericides than the
ligand. This enhancement in antibacterial activity is rationalized

INDOLE BASED BIS-LIGAND
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The present article describes a novel bis-ligand having in-
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SUPPLEMENTARY DATA
Figure 1 and Figure 2 for FTIR of ligand. For coordination
polymers, see the supplementary data. The thermogram of lig-
and and its coordination polymers are shown in Figure 5 in
supplementary data.
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