The Synthesis and Characterization of s-Triazine-Cored Tripodal Structure and Its Salen/Salophen-Bridged Fe/Cr(III) Capped Complexes

Article abstract of DOI:10.1002/jhet.2642

A novel Schiff base compound was synthesized, and its complexation properties with Fe(III) and Cr(III) were investigated. Tripodal ligand was synthesized by the reaction of s-triazine and 4-hydroxybenzaldehyde. Then a Schiff base involving 8-hydroxyquinoline was synthesized by the reaction of 5-aminomethyl-8-hydroxyquinoline (QN) and 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD) in methanol/chloroform media. The obtained Schiff base (QN-TRIPOD) was then reacted with four trinuclear Fe(III) and Cr(III) complexes including tetradentate Schiff bases N,N′-bis(salicylidene)ethylenediamine (salenH₂)/bis(salicylidene)-o-phenylenediamine (SalophenH₂). The synthesized ligand and complexes were characterized by means of elemental analysis carrying out¹H NMR, FTIR spectroscopy, thermal analyses, and magnetic susceptibility measurements. Finally, metal ratios of the prepared complexes were determined by using atomic adsorption spectrometry.

Full text of DOI:10.1002/jhet.2642

Month 2016 The Synthesis and Characterization of s-Triazine-Cored Tripodal Structure
and Its Salen/Salophen-Bridged Fe/Cr(III) Capped Complexes
*
Erhan Karatas and Halil Ismet Ucan
Department of Chemistry, Science Faculty, Selcuk University, 42075, Konya, Turkey
*
E-mail: erhankaratas@gmail.com
Received January 6, 2016
DOI 10.1002/jhet.2642
Published online 00 Month 2016 in Wiley Online Library (wileyonlinelibrary.com).
A novel Schiff base compound was synthesized, and its complexation properties with Fe(III) and Cr(III)
were investigated. Tripodal ligand was synthesized by the reaction of s-triazine and 4-hydroxybenzaldehyde.
Then a Schiff base involving 8-hydroxyquinoline was synthesized by the reaction of 5-aminomethyl-8-
hydroxyquinoline (QN) and 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD) in methanol/chloroform
media. The obtained Schiff base (QN-TRIPOD) was then reacted with four trinuclear Fe(III) and Cr(III)
complexes including tetradentate Schiff bases N,N′-bis(salicylidene)ethylenediamine (salenH2)/bis
(salicylidene)-o-phenylenediamine (SalophenH2). The synthesized ligand and complexes were characterized
by means of elemental analysis carrying out 1H NMR, FTIR spectroscopy, thermal analyses, and magnetic
susceptibility measurements. Finally, metal ratios of the prepared complexes were determined by using
atomic adsorption spectrometry.
J. Heterocyclic Chem., 000, 00 (2016).
INTRODUCTION
Metal complexes of the “Salen-type” ligands have been
considered as interesting species in many fields of chemi-
cal research because of some specific properties. Fe-Salen
complexes have been extensively studied in the solid state
and in solution [14,15]. Kessel and Hendrickson [16] have
studied Schiff base complexes of iron(III) incorporating p-
quinine bridges. The reactions of {[Fe(Salen)]2O} with
carboxylic acids have been described by Wollmann and
Hendrickson [17]. Uysal and Ucan have reported the syn-
thesis and characterization of 1,3,5,-tricarboxylato and
monocarboxylato bridges with [Salen or SalophenFe(III)/
Cr(III)] [18]. Chromium(III) complexes of Salen-type
Schiff bases have been found to enhance insulin activity.
And also, various metal-Salen complexes such as manga-
nese(III), chromium(III), and nickel(II)-Salen complexes
have been used for the epoxidation of olefins [19–21].
The aim of the present study is synthesis of novel
tridirectional–trinuclear systems and to present their effects
on magnetic behavior of [Salen/SalophenFe(III)] and
[Salen/SalophenCr(III)] capped complexes. The reaction of
trimeric cyanuric (C3N3Cl3) with 3 equivalent of 4-
hydroxybenzaldehyde in benzene media has given the de-
sired trisaldehyde in a single step, coded as 2,4,6-tris(p-
formylphenoxy)-1,3,5-triazine (TRIPOD) [22]. Trisaldehyde
was then converted to a novel Schiff base [5-aminomethyl-
8-hydroxyquinoline (QN)-TRIPOD] with QN. Finally, its
1,3,5-Triazine (or s-Triazines) derivatives are known for
a long time and widely used as herbicides, dyestuffs, ex-
plosive, surface active agents, drugs, or polymer-like
melamine–formaldehyde that has excellent thermal and
electrical properties [1–5]. Furthermore, a very large num-
ber of supramolecular noncovalently bond assemblies be-
tween melamine and barbituric or cyanuric acid
derivatives have been reported [6,7]. The chemistry of
these compounds has been studied intensively, and they
are the subject of many reviews [8–10].
8-Hydroxyquinoline, a monoprotic bidentate chelating
agent, has received increased attention recently because
its most representative metalloquinolate, aluminum tris(8-
hydroxyquinoline), has served as the emitting material in
organic light emitting diodes [11]. 8-Hydroxyquinoline
metal chelates are presently considered as one of the most
reliable electro-transporting and emitting materials applied
in molecular-based organic light emitting diodes for their
thermal stability, high fluorescence, and excellent
electron-transporting mobility [12]. In addition, a large
number of 8-hydroxyquinoline derivatives have been syn-
thesized and shown to be bioactive. For example, it was re-
ported that some 8-hydroxyquinoline derivatives posses
antitumor and antimicrobial activities [13].
© 2016 Wiley Periodicals, Inc.

2
E. Karatas and H. I. Ucan
Vol 000
complexation properties investigated with Fe(III) and Cr
(III). It may be useful to stress at this point that the new prod-
ucts mentioned previously are the main results of this work.
at 1534–1552cmꢀ1. In the complexes, these C¼N bands
shift to lower frequencies for cap parts of the complexes, in-
dicating that the OH groups of the tripodal oxy-Schiff base li-
gand are coordinated to metal center of the tripodal–trinuclear
complexes [18]. In the ligand QN-TRIPOD, the band at
3407cmꢀ1 can be assigned to the –OH group vibrations.
In the tripodal–trinuclear complexes, which these bonds
disappear, is evidence that –OH group coordinated to
metal center of ligand complexes. We have suggested that
oxygen atom (for complexes I, II, III, and IV) ꢀOH
group coordinated to metal centers. In the tripodal–
trinuclear complexes, the bands in the 547–565 and
464–475 cmꢀ1 ranges can be attributed to the M–N and
M–O stretching modes (Fig. 1) [25,27].
RESULT AND DISCUSSION
2,4,6-Tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD)
was prepared trough the reaction of 2,4,6-Trichloro-1,3,5-
triazine and 4-hydroxybenzaldehyde in the presence of
Na2CO3. Then, the tripodal Schiff base (QN-TRIPOD)
was synthesized using TRIPOD and 5-aminomethyl-8-
hydroxyquinoline
in
methanol/chloroform
media
(Scheme 1). The result of this reaction, “Tripodal Oxy-
Schiff base” was obtained as a new Schiff base. QN-
TRIPOD was characterized by elemental analyses, 1H
NMR, and FTIR spectroscopy. The FTIR spectrum of
QN-TRIPOD is depicted in Figure 2. As can be seen in
Figure 2, the obtained QN-TRIPOD was confirmed by
the disappearance of aldehyde band (1702cmꢀ1) in TRI-
POD and the appearance of the imine bands belong to a
QN-TRIPOD compound (CH¼N) at 1636cmꢀ1. QN-
TRD prepared in this way was obtained in nearly quantita-
tive yield and high purity. Synthetic strategy for preparing
Tripodal–Trinuclear uses a complex as a “ligand” that con-
tains a potential donor group capable of coordinating to an-
other ligand. {[Fe/Cr(Salen)]2O} and {[Fe/Cr(Salophen)]
2O} have been chosen as ligand complex because they
can coordinate to another ligand [26]. These complexes
are the first examples of tripodal–trinuclear complexes
bridged by catechol groups and pyridine to the iron and
chromium centers (Scheme 2). The vibrations of three
strong bands the azomethine ꢀC¼N, triazine C¼N, and
OH of the free ligand are observed at 1636, 1562, and
3407 cmꢀ1 range in the FTIR spectra. FTIR spectra of all
trinuclear complexes show C¼N stretching bands for the
azomethine group at 1601–1623cmꢀ1, for the triazine
bands at 1565–1574 cmꢀ1, for the cap parts of the complexes
In order to identify the structures of the new Tripodal Oxy-
Schiff base and TRIPOD, 1H NMR were used. Spectra were
recorded in DMSO-d6. And the expected chemical shifts
were observed. The obtained compound was confirmed by
the disappearance of aldehyde protons (9.97ppm) in TRI-
POD, and the appearance of the imine protons belongs to a
QN-TRIPOD compound (ꢀCH¼N) at 8.91 ppm. 1H NMR
spectra also confirmed the structure of the synthesized Schiff
base. And also, the other 1H NMR spectrum values of QN-
TRIPOD were observed as expected. For the complex struc-
tures because the Fe(III) and Cr(III) metals are paramagnetic
1H NMR spectra did not be taken (Fig. 2).
The magnetic behavior of Fe(III) and Cr(III) complexes is
in accord with proposed trinuclear structures. The magnetic
moments of the trinuclear complexes indicate paramagnetic
properties with magnetic susceptibility values per atom of
1.63, 1.72, 3.51, and 3.63 BM, respectively. The equation
pffiffiffiffiffiffi
simplifies to: μeff : ¼ 2:84 χMT BM. The measured μeff
can be compared with the calculated value. The spinning of
unpaired electrons in paramagnetic complexes of d-block
metal ions creates a magnetic field, and these spinning elec-
trons are in effect small magnets. The magnetic susceptibil-
ity, μ, because of the spinning of the electrons is given by
pffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffi
the spin-only formula: μs ¼ nðn þ 2Þ , where n is the
Scheme 1. Synthesis of a novel Schiff base bearing 5-aminomethyl-8-hydroxyquinoline (QN-TRIPOD).
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s-Triazine-Cored Tripodal Structure and Its Fe/Cr(III) Capped Complexes
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Scheme 2. Synthesis of tripodal–trinuclear complexes of QN-TRIPOD.
Figure 1. FTIR spectra of (a) 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD), (b) 2,4,6-tris(2,5-aminomethyl-8-hydroxyquinoline-4′-formylphenoxy)-1,3,5-tri-
azine (QN-TRIPOD), (c) tripodal–trinuclear complex compound (II). [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
number of unpaired electrons. When n is 1 and 3, the calcu-
lated values of μs are 1.73 and 3.87 BM. The measurements
and calculated values of μ show us that the {[Fe(Salen/
saloph)]2O} and {[Cr(Salen/Salophen)]2O} containing com-
pounds appear to be represented by the electronic structures
of t2g5eg0 and t2g3eg0. The magnetic data for the {[Fe
(Salen)]2O}, {[Fe(Salophen)]2O}, {[Cr(Salen)]2O}, and {[Cr
(Salophen)]2O} tripodal complexes demonstrate strong
agreement with the d5 and d3 metal ion in an octahedral
structure. This consequence is supported by the results of
the elemental analyses also suggesting that these trinuclear
complexes have an octahedral structure [1,18,27].
TRIPOD} were investigated. And their plausible degradation
schemes are presented in Table 1. Complexes at 22–100°C are
because of the loss of moisture [23]. It was determined in two
steps. Firstly, [Fe/Cr/(Salen/Salophen)] caps have been left the
main structure at 244–556°C. After, when the sample was
heated to 556°C, main body started to decompose. At this step,
the weight loss carried out the temperature at 556–703°C.
Thermal measurement has been taken until 1000°C. The
second steps have corresponded to the decompositions of
the aromatic groups and the residual ligand. The final de-
composition products were metaloxides, quinoline, and
the triazine ring. The observed weight losses for com-
plexes are in good agreement with the calculated values
[1,25,27] (Fig. 3).
The thermal properties (TG, DTA) of all tripodal com-
plexes {[Fe/Cr/(Salen/Salophen)] capped complexes of QN-
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E. Karatas and H. I. Ucan
Vol 000
Figure 2. The 1H NMR spectra of TRIPOD and QN-TRIPOD.
Table 1
Decomposition steps with the temperature range and weight loss for complexes.
Compound
Step no
Temp. range (°C)
Weight loss found (Calcd.) (%)
49.41 (49.44)
Fragmenta
I
1
2
3
4
1
2
3
4
1
2
3
4
1
2
3
4
101–244
244–469
469–703
703–980
100–304
304–556
556–664
664–998
105–292
292–534
534–692
692–987
103–256
256–497
497–689
689–976
N2, CO2, C2H4, CO, NH3,H2, C6H6
N2, CO2, C2H4, CO, NH3,H2, C6H6
N2, CO2, CO, NH3,H2, C6H6
II
46.11 (49.10)
50.98 (53.03)
51.78 (53.91)
III
IV
N2, CO2, CO, NH3,H2, C6H6
aThese are conjectural data.
CONCLUSION
centers. Their structures were characterized by means of ele-
mental analysis carrying out 1H NMR, FTIR spectroscopy,
thermal analyses, and magnetic susceptibility measurements.
Finally, metal ratios of the prepared complexes were deter-
mined by using atomic adsorption spectrometry. The mag-
netic data for tripodal complexes show good harmony with
the d5 and d3 metal ions in an octahedral structure.
In this study, a new tripodal s-triazine based Schiff
base “2,4,6-tris(2,5-amminomethyl-8-hydroxyquinoline-4′-
formylphenoxy)-1,3,5-triaazine” was synthesized and its
complexes were prepared. Synthetic strategy for preparing
tripodal–trinuclear uses a complex as a ligand that contains
a potential donor group capable of coordinating to the other
ligand. We have chosen [Fe(Salen)]2O, [Fe(Salophen)]2O,
[Cr(Salen)]2O, and [Cr(Salophen)]2O as “ligand complexes”
because they can coordinate to the other ligands. These com-
plexes are the examples of tripodal–trinuclear complexes
bridged by catechol groups to the iron and chromium
EXPERIMENTAL
All chemicals were purchased from Aldrich, Merck, and
Alfa-Easer. The linking agent, 2,4,6-trichloro-1,3,5-triazine
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s-Triazine-Cored Tripodal Structure and Its Fe/Cr(III) Capped Complexes
5
Figure 3. The TGA-DTA diagram of I. [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
(abbreviated as cyanuric chloride, mp 145–146°C), was ob-
tained from Aldrich. Cyanuric chloride was purified by re-
crystallizations from pure petroleum ether (60–90°C) [23].
1H NMR spectra were recorded by the Varian, 400MHz
spectrometer at room temperature. FTIR spectra were re-
corded using a Perkin Elmer Spectrum 100 with Universal
ATR Polarization Accessory. Melting points were deter-
mined by Büchi Melting Point B-540 instrument. Elemen-
tal analyses were carried out using a LECO-CHNS-932
elemental analyzer. Thermal analysis (TG) was carried
out with a Seteram thermogravimetric analyzer. The sam-
ple weight was 15–17 mg. TG curves were obtained at
the heating rate of 10°C/min from 22 to 1000°C under argon
atmosphere with a gas flow rate of 20mL/min. Metal con-
tents in complexes were determined using Unicam 929
AAS spectrometer. Magnetic susceptibilities of metal com-
plexes were measured at 296K using a Sheerwood Scientific
MX Gouy magnetic susceptibility apparatus and carried out
using the Gouy method with Hg[Co(SCN)4] as calibrant.
solid was collected on a filter and washed with
condensed hydrochloric acid three or four times instead
of acetone. Dried in vacuo at 40°C. Yield: 91.4%, mp:
280°C. FTIR (cmꢀ1): 3298 (ꢀOH), 1595 (pyridine ring),
1550, 1493 (aromatic), 1388 (C–N), 695 (C–Cl).
Synthesis of 5-aminomethyl-8- hydroxyquinoline.
QN
and
2-(hydroxyquinoline-5-ylmethyl)-isoquinoline-1,3-
diketone were synthesized according to the procedure
[24]. 2-(Hydroxyquinoline-5-ylmethyl)-isoquinoline (2.0g,
6.5mmol) was added to the concentrated hydrochloric acid
(50mL) stirred at room temperature 1h, then refluxed until
the mixture become transparent. After cooling to room
temperature, the resulting solid was filtered, and the filtrate
was concentrated on a rotary evaporator. The resulting
yellow residue was dissolved in 10mL water, then
triethylamine was added, until greenish solid formed,
filtered. The solid formed was washed with cold water,
dried under vacuum cabinets at room temperature to give
compound QN. FTIR (cmꢀ1): 3292, 2974, 2650, 1558,
1508, 1454, 1298, 1077. 1H-NMR (DMSO-d6, ppm):
δ=4.03 (s, 2H, –CH2), 7.01 (d, 1H, Ar–H), 7.42 (d, 1H,
Ar–H), 7.56 (m, 1H, Ar–H), 8.53 (d, 1H, Ar–H), 8.82 (d,
1H, Ar–H) (Scheme 3).
The effective magnetic moments, μeff, per metal atom was
pffiffiffiffiffiffi
calculated from the expression: μeff : ¼ 2:84 χMT B.M.,
where χM is the molar susceptibility.
Synthesis of 5-chloromethyl-8-hydroxyquinoline.
5-
synthesized
slightly
Synthesis of TRIPOD.
TRIPOD was synthesized
Chloromethyl-8-hydroxyquinoline
was
according to the literature procedure [22]. p-
Hydroxybenzaldehyde (1.6 g, 1.31mmol) and 2,4,6-
Trichloro-1,3,5-triazine (0.6 g, 3.25 mmol) were added to
a suspension of Na2CO3 (10 g) in 50mL of benzene. The
mixture was refluxed for 20h. The reaction mixture was
then cooled, and the solid was removed by filtration and
washed with hot AcOEt twice. The filtrate was extracted
according to the literature [12] with
a
modification. Thirty-seven percent of formaldehyde
(6.4 mL, 0.08 mol) was added to a solution of 8-
hydroxyquinoline (5.84 g, 0.04mmol) in concentrated
hydrochloric acid (50 mL). The mixture was treated with
hydrogen chloride gas until the solid formed and allowed
to stand overnight at the room temperature. The yellow
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E. Karatas and H. I. Ucan
Vol 000
Scheme 3. Synthetic route for 5-aminomethyl-8-hydroxyquinoline (QN). Reagents and reaction condition: (i) formaldehyde, gaseous HCl, room tem-
perature 12 h; (ii) potassium phtalimide, DMF, 150°C 5 h, (iii) concentrated HCl, reflux.
Table 2
Some physical properties, effective magnetic moments, elemental analyses, and AAS analyses of the ligands and complexes.
Found (Calcd.)(%)
μeff
(BM)
mp
(°C)
Yield
(%)
Compound
Formula
Color
White
Greenish
Cream
Dark Brown
Dark Green
Brown
C
N
H
M
TRIPOD
QN
QN-TRIPOD
I
II
III
IV
C
24H15N3O6
C10H10N2O
C54H39N9O6
C102H78N15O12Fe3
C102H78N15O12Cr3
C114H78N15O12Fe3
C114H78N15O12Cr3
—
—
—
1.63
3.51
1.72
3.63
174
96
85
80
70
75
65
70
60
65.26 (65.31)
68.84 (68.95) 16.12 (16.08) 5.72 (5.79)
71.22 (71.28) 13.91 (13.85) 4.28 (4.32)
65.34 (65.40) 11.31 (11.22) 4.12 (4.20) 8.83 (8.94)
65.72 (65.80) 11.34 (11.28) 4.11 (4.22) 8.43 (8.38)
67.73 (67.87) 10.49 (10.41) 3.83 (3.90) 8.22 (8.30)
68.19 (68.26) 10.52 (10.47) 3.83 (3.92) 7.69 (7.78)
9.61 (9.52)
3.39 (3.43)
—
—
—
156
325a
350a
330a
365a
Green
aDecomposition temperature.
with 10% Na2CO3 twice and with H2O once. The organic
layer was dried over anhydrous Na2SO4 and then
concentrated. The white powder was recrystallized from
20mL of AcOEt.
mixture were refluxed for 4 h. The mixture was allowed
to cool to room temperature, and the obtained product
was filtered, washed with water, ethanol and diethyl
ether, and dried in vacuo (0.4 bar) at 60°C. The FTIR
(cmꢀ1) data for I: 2859 (CH), 1620 (ꢀCH¼N), 1574
(C¼N triazine), 1377 (COC), 547 (M–N), 469 (M–O). II:
2862 (CH), 1603 (–CH¼N), 1575 (C¼N triazine), 1369
(COC), 551 (M–N), 475 (M–O). III: 2824 (CH), 1615 (–
CH¼N ), 1578 (C¼N triazine), 1368 (COC), 549 (M–N),
464 (M–O). IV: 2829 (CH), 1600 (–CH¼N), 1578 (C¼N
triazine), 1368 (COC), 565 (M–N), 471 (M–O). The
elemental analyses, magnetic, and physical properties of
the synthesized complexes are given in Table 2.
Synthesis
of
QN-TRIPOD.
5-Aminomethyl-8-
hydroxyquinoline (0.522g, 3mmol) was added drop by
drop to a solution of 2,4,6-tris(p-formylphenoxy)-1,3,5-
triazine (0.442g, 1mmol) in 30mL methanol/chloroform
solution (1/1), and then three drops of concentrated H2SO4
was added as catalyst in 50mL methanol/chloroform
solution (1/1). The mixture was then stirred under reflux
for 24h. The mixture was cooled to room temperature and
yellow powder product was filtered. The precipitate was
washed with cool ethanol. FTIR (cmꢀ1): 3407 (ꢀOH),
1636 (ꢀCH¼N), 1562 (C¼Ntriazine); 1H NMR (DMSO-d6):
δ=4.41 (s, 6H, -CH2), 7.09 (d, 3H, ArH), 7.56 (d, 3H,
ArH), 7.63–7.67 (m, 15H, ArH), 8.1 (s, 3H, ꢀCH), 8.57 (d,
3H, ArH), 8.89 (d, 3H, ArH), 10.10 (s, 3H, OH).
Acknowledgment. We thank the Scientific Research Projects
Foundation of Selcuk University (SUBAP-Grant Number
2009/09101036) for financial support of this work produced
from a part of Erhan Karatas’s PhD Thesis.
Preperation of ligand complexes.
[Fe(Salen)]2O, [Fe
(Salophen)]2O, [Cr(Salen)]2O, and [Cr(Salophen)]2O
were prepared by addition of concentrated ammonia
solution until alkaline. It was to the hot EtOH solutions
of [Fe(Salen)]Cl, [Fe(Salophen)]Cl, [Cr(Salen)]Cl, and
[Cr(Salophen)]Cl, respectively [25].
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