Journal of Hazardous Materials 175 (2010) 532–539
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Journal of Hazardous Materials
journal homepage: www.elsevier.com/locate/jhazmat
Synthesis and characterization of dendrimeric melamine cored
[salen/salophFe(III)] and [salen/salophCr(III)] capped complexes and
their magnetic behaviors
S¸ aban Uysal
∗
, Ziya Erdem Koc¸
Department of Chemistry, Faculty of Science, Selcuk University, Campus of Alaaddin Keykubat, 42075 Selcuklu, Konya, Turkey
article info
Article history:
Received 10 August 2009
Received in revised form 2 October 2009
Accepted 13 October 2009
Available online 20 October 2009
Keywords:
s-Triazine
Melamine
Cyanuric chloride
Salen
Saloph
Schiff bases
abstract
2,4,6-Tris(4-hydroxybenzimino)-1,3,5-triazine [1] 2 has been synthesized from the reaction of 1 equiv.
melamine (2,4,6-triamino-1,3,5-triazine) and 3 equiv. 4-hydroxybenzaldehyde. Then, 2,4,6-tris(4-(4,6-
dichloro-1,3,5-triazine-2-yloxy)benzimino)-1,3,5-triazine 3 has been synthesized from the reaction of
1 equiv. 2 and 3 equiv. cyanuric chloride. And then, two new triazine centered dendrimeric ligands
2,4,6-tris(4-(4,6-bis(4-carboxyphenyloxy)-1,3,5-triazine-2-yloxy)benzimino)-1,3,5-triazine 4 and 2,4,6-
tris(4-(4,6-bis(3,5-dicarboxyphenyloxy)-1,3,5-triazine-2-yloxy)benzimino)-1,3,5-triazine 5 have been
synthesized from the reaction of 1 equiv. 3 and 6 equiv 4-hydroxybenzoic acid or 5-hydroxyisophtalic
acid. Finally, eight new multinuclear Fe(III) and Cr(III) complexes involving tetradenta Schiff bases
N,N
′
-bis(salicylidene)ethylenediamine-(salenH
2
) or bis(salicylidene)-o-phenylene diamine-(salophH
2
)
with 4 or 5 have been synthesized and characterized by means of elemental analysis,
1
H NMR, FT-IR
spectroscopy, thermal analyses and magnetic susceptibility measurements. The complexes can also be
characterized as low-spin distorted octahedral Fe(III) and Cr(III) bridged by carboxylic acids.
© 2009 Elsevier B.V. All rights reserved.
1. Introduction
An important class of compounds having anticancer, antitumor,
antiviral and antifungal activity consists of substituted s-triazine
derivatives. These compounds have been used in the treatment of
depression and hence gained considerable significance. These are
valuable bases for estrogen receptor modulators [2] and also used
as bridging agents to synthesize herbicides and in the production
of drugs or polymers [3].
Melamine resins have been used in many applications includ-
ing the manufacture of plastic dishes under the trade name Melmac.
1,3,5-Triazine derivatives are widely used as herbicides [4], drugs
[5] or polymers [6], like melamineformaldehyde that has excel-
lent thermal and electrical properties [7]. Phenolic melamine has a
good non-flammability owing to containing nitrogen in its chemical
structure [8].
We have reported here that dendrimeric Schiff bases including
hexacarboxylic and dodecacarboxylic groups have been synthe-
sized to be a new template. The reaction of melamine (C
3
N
6
H
6
)
with 3 equiv. of 4-hydroxybenzaldehyde in benzene has given the
desired triazomethine groups and triphenolic groups in a single
step. Phenolic–OH groups [9,10] were then reacted to trimeric
∗
Corresponding author. Tel.: +90 532 303 30 35.
E-mail addresses: uysal77@hotmail.com, suysal@selcuk.edi.tr (S¸ . Uysal).
cyanuric chloride (C
3
N
3
Cl
3
) as single directional at 0–5
◦
C. Then,
the obtained product was reacted under reflux with 6 equiv.
4-hydroxybenzoic acid and 6 equiv. 5-hydroxyisophthalic acid
[11–15]. It may be useful to stress at the point that the new prod-
ucts mentioned above are the main output of this work. These are
the first in the literature and we call them “oxy-Schiff Bases” due
to literature [9,10].
The magnetochemical properties of the -oxo-bridged com-
plexes [{Fe(salen)}
2
O] [(salenH
2
= N,N
′
-bis(salicylidene)ethylene
diamine)] and [{Fe(saloph)}
2
O] [(salophH
2
= bis(salicylidene)-2-
phenylenediamine)] and their X-ray studies have widely been
presented in the literature [16–19]. The reaction of [{Fe(salen)}
2
O]
with carboxylic acids have been given by Wollmann and Hendrick-
son [20].
Chromium is a unique transition metal ion, which has been
established to be biologically significant at all the levels of liv-
ing organisms [21]. Out of the two stable oxidation states of
chromium, -VI and -III, trivalent chromium has been shown to play
a positive role in controlling carbohydrate and lipid metabolism
[22]. A Schiff base complex of chromium(III), [Cr(salen)(OH
2
)
2
]
+
,
was found to enhance insulin activity, and insulin derived
with the same was found to exhibit higher activity in glucose
metabolism in animal models when compared with either free
insulin or other derivatives [23,24]. Their asymmetric catalytic
reactions have been described including oxidations, additions
and reductions such as epoxidation of olefins, epoxide ring
0304-3894/$ – see front matter © 2009 Elsevier B.V. All rights reserved.
doi:10.1016/j.jhazmat.2009.10.038