Fluorescence properties and electrochemical behavior of some schiff bases derived from n-aminopyrimidine

Article abstract of DOI:10.1007/s10895-013-1303-x

A series of Schiff bases (L ₁, L ₂ and L ₃ ) were prepared by refluxing aromatic aldehydes with N-Aminopyrimidine derivatives in methanol and ethanol. The structures of synthesized compounds were characterized by FTIR, ¹H NMR, ¹³C NMR and microanalysis. The electrochemical behaviors of the Schiff base ligands were also discussed. Moreover, the evaluation of absorption and emission properties of the structures were carried out in five different solvents. The products show visible absorption maxima in the range of 304-576 nm, and emission maxima from 636 to 736 nm in all solvents tested.

Full text of DOI:10.1007/s10895-013-1303-x

J Fluoresc (2014) 24:389–396
DOI 10.1007/s10895-013-1303-x
ORIGINAL PAPER
Fluorescence Properties and Electrochemical Behavior
of Some Schiff Bases Derived from N-Aminopyrimidine
Mehmet Gulcan & Ümit Doğru & Gülsiye Öztürk &
Abdulkadir Levent & Esvet Akbaş
Received: 28 July 2013 /Accepted: 11 September 2013 /Published online: 21 September 2013
#
Springer Science+Business Media New York 2013
Abstract A series of Schiff bases (L1, L2 and L3) were
prepared by refluxing aromatic aldehydes with N-
Aminopyrimidine derivatives in methanol and ethanol. The
structures of synthesized compounds were characterized by
chemistry [1–5]. Moreover they have increasingly importance
in the pharmacological, dye, and plastic industries as well as in
the field of liquid crystal technology [6–10]. Pyrimidine is a
very important group of compounds that has been extensively
studied due to their occurrence in the living systems [11].
Pyrimidines are reported to have broad spectrum of biological
activities. Some are endowed with antitumor [12], antiviral [13],
anti-inflammatory [14], antipyretic [15], antimicrobial [16], and
antifungal [17] properties. During last few decades there has
been great interest in the chemistry of transition metals associ-
ated with nitrogen, oxygen and sulfur donor ligands, such as five
and six membered heterocyclic pyrazoles, pyridazines and
pyrimidines [18–21].
1
FTIR, H NMR, 13C NMR and microanalysis. The electro-
chemical behaviors of the Schiff base ligands were also
discussed. Moreover, the evaluation of absorption and emis-
sion properties of the structures were carried out in five
different solvents. The products show visible absorption max-
ima in the range of 304–576 nm, and emission maxima from
636 to 736 nm in all solvents tested.
.
.
Keywords Schiff base fluorescence
.
N-Aminopyrimidine electrochemistry
In this work the Schiff bases containing a pyrimidine
ring were synthesized, characterized and their fluorescence
features were determined in different solvents. The com-
pounds were characterized by elemental analysis, FT-IR, 1H
and 13C NMR techniques. Moreover, the electrochemical
properties of the Schiff bases were investigated.
Introduction
Schiff bases are known to be very important class of organic
compounds because of their ability to form stable complexes
with many different transition metal and rare-earth metal ions in
various oxidation states and have the potential to be used in
different areas such as catalysis, metallic deactivators, separation
processes, electrochemistry, bioinorganic and environmental
Results and Discussion
The present work involves the spectroscopic investigation
of the Schiff base ligands (L1, L2 and L3) derived from
pyrimidine amine. The synthesis protocol of Schiff base
ligands has been shown in Fig. 1.
The IR spectra of the L3 ligand exhibit several bands in
the region of 400–4,000 cm−1. The IR spectrum of the
ligand showed a ν(C=N) peak at 1,599 cm−1 and the
absence of ν(C=O) at ~1,680 cm−1 and ν(NH2) peaks
around 3,250–3,300 cm−1 is because of Schiff base
condensation. The absorption band at 1,643 cm−1 is
assigned to benzoyl ν(C=O) moiety. Pyrimidine ring
showed characteristic stretching absorption bands at the
3,064 cm−1[22].
:
M. Gulcan (*) E. Akbaş
Department of Chemistry, Faculty of Science,
University of Yuzuncu Yil, 65080 Van, Turkey
e-mail: mehmetgulcan65@gmail.com
:
Ü. Doğru G. Öztürk (*)
Department of Chemistry, Faculty of Science,
University of Dokuz Eylül, 35160 Tınaztepe, Izmir, Turkey
e-mail: gulsiyeozturk@yahoo.com
A. Levent
Health Services Vocational College, Batman University,
72100 Batman, Turkey

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J Fluoresc (2014) 24:389–396
Fıg. 1 Synthesis protocol of Schiff base ligands
1
The H NMR and 13C NMR spectra of the Schiff base
Fluorescence Features
ligand were carried out at room temperature in CDCl3 and
DMSO-d6, respectively (Figs. 2 and 3).
The absorption and emission properties of the Schiff bases,
L1, L2 and L3 were studied at different solvents with different
polarities of acetonitrile, methanol, ethanol, tetrahydrofuran
and toluene and data obtained are presented in Table 1. The
first absorption band of the compounds at λmax between 304
and 418 nm may correspond to the π–π* transition of the
azomethine group C=N while the second band between 383
and 576 nm may correspond to the n–π* transitions. As the
polarity of the solvent is increased, while the absorption
maxima of L3 is red shifted, the absorption maxima of L2
and L1 are blue shifted, except for L1 in toluene.
While the solvent polarity has nearly negligible effect on
the emission maxima of the compounds, one interesting
result is that only in ethanol the emission maxima of all
the compounds is red shifted in comparison to all other
solvents studied, presumably due to intramolecular proton
transfer from the solvent to each derivative or hydrogen
1
The H NMR spectrum of ferrocenyl Schiff base (L3)
showed the singlet at 8.99 ppm and 8.48 ppm were due to
azomethine proton and pyrimidine ring (C–H) proton in the
spectrum of the ligand, respectively. The multisignals cor-
responding aromatic protons appeared between at 7.80–
7.33 ppm [23, 24]. The spectrum of ferrocenyl Schiff base
exhibited cyclopentadienyl ring proton signals between at
4.40 and 4.84 ppm [25].
13C NMR spectrum (Fig. 3) displayed characteristic signals
at 192.1, 170.9 and 170.5 ppm due to the (OC-Ar), (C=O,
pyrimidine) and (−C6, pyrimidine ring) of the L3 ligand, respec-
tively. The singlet peaks at 151.8 ppm was due to azomethine
carbon of the ligand [24]. On the other hand, the spectrum of the
ligand showed peaks in the region of 137.5–115.6 ppm, due to
aromatic carbons. The observed signals between 75.2 and
69.7 ppm belongs to cyclopentadienyl ring carbons [26].

J Fluoresc (2014) 24:389–396
391
Fıg. 2 1H NMR spectrum of L3
Schiff base
Fıg. 3 13C NMR spectrum of
L3 Schiff base

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J Fluoresc (2014) 24:389–396
Table 1 Adsorption and
fluorescence emission data for
compounds L1, L2 and L3
1
.max
2
.max
1
2
emis.
Compound Solvent
λabs
λabs
εmax
εmax
λ
Δλ
Φ
Max
L3
L2
L1
Acetonitrile
346
346
348
358
360
348
352
344
342
304
376
348
352
367
418
460
478
480
470
470
468
453
464
475
383
424
440
464
443
576
3800
50900
3700
700
10100
1800
5300
400
713
715
731
715
714
655
657
687
655
656
640
639
736
642
640
253
237
251
245
244
187
204
223
180
273
216
199
272
199
64
0,0132
0,0004
0,0054
0,0013
0,3732
0,0041
0,0144
0,0312
0,0247
0,0123
0,0040
0,0030
0,0021
0,1920
0,0382
Methanol
Ethanol
Tetrahydrofuran
Toluene
22600
2100
Acetonitrile
Methanol
8200
2700
7200
1200
700
20000
9200
Ethanol
Tetrahydrofuran
Toluene
5700
43000
14900
41000
9600
16400
7000
7900
2700
1000
1900
Acetonitrile
Methanol
Ethanol
Tetrahydrofuran
Toluene
9700
14100
bonding. The longest wavelength emission maxima are
observed for L3 in the range of 714 and 731 nm, while L2
and L1 fluorescent nearly in the similar wavelength range,
except for L1 in ethanol (Fig. 4).
The compounds exhibited moderate Stokes’ shift values
ranging from 64 to 272 nm, which confers to the advantage
of better spectral resolution in emission based studies.
The fluorescence quantum yields of compounds were
determined by using Rhodammine 101 as a standard sam-
ple in ethanol. The highest quantum yield value was
obtained for L3 in tolune, for L2 in ethanol and for L1 in
tetrahydrofuran (Table 1).
The photostability of the derivatives in dimethylformamide,
acetonitrile, methanol, ethanol, tetrahydrofuran and toluene
was determined with a steady-state spectrofluorimeter in
time-based mode. The data were acquired at their maximum
emission wavelengths. According to the data collected after
1 h, there was no change in the fluorescence intensities of the
compounds (Fig. 5).
Electrochemical Analysis
The electrochemical properties of the present compounds
were investigated by Cyclic voltammetric (CV) and on a
glassy carbon electrode in dimethylformamide (DMF) con-
taining 0.1 M tetrabutylammonium perchlorate (TBAP), in
the concentration of 1×10−3 M vs. Ag/AgCl. The electro-
chemical data in peak potentials are reported in Table 2.
In the cathodic direction from +1.5 V to −2.3 V at scan
rate of 100 mV s−1, the CV of L1 is characterized by three
cathodic waves (Ic, IIc and IIIc at about −1.84, −1.41 and
−1.17 V, respectively) and anodic waves were not observed
as depicted by CV given in Fig. 6a. These peaks were
irreversible. At higher scan rates (> 100 mV s−1) the oxi-
dation process peaks became more intense (Fig. 7a).
The electrochemical behavior of the L2 is presented in
Fig. 6b. In the CV measurements upon scanning cathodi-
cally at the negative potential side (from +1.5 to −2.3 V at
100 mV s−1), the CVof L2 is characterized by one cathodic
L
3
L
L
2
1
Fıg. 4 Fluorescence spectra of L (····), L (–) and L (– –) compounds
Fıg. 5 Photostability test results of L1, L2 and L3 in tetrahydrofuran
after 1 h of monitoring
·
1
2
3
in ethanol

J Fluoresc (2014) 24:389–396
393
Table 2 Voltammetric results at
scan rate of 100 mVs−1 vs. Ag/
AgCl. Ec: cathodic potential,
Ea: anodic potential
Compound
Ec
Ea
L1
L2
L3
Ic:-1.84, IIc:-1.41, IIIc:-1.17
Ic:-1.99, IIc:-1.65, IIIc:-0.65, IVc:-030
Ic:-1.36, IIc:-1.62, IIIc:-2.05
Ia′:+0.74 IIIa:-0.40
Ia′:+1.42
peak (Ic at about −1.99 V) and one anodic wave (Ia’ at
about +0.74 V) (Fig. 6b). At higher scan rates (≥
200 mV s−1) three new cathodic waves were located at
about −1.65, −0.65 and −0.30 V (IIc, IIIc and IVc,
respectively) and a new anodic peak was observed at
about IIIa (at ca. −0.40 V) (Fig. 7b). ΔEp for IIIa/IIIc
from this redox couple was also found to be 250 mV.
This is a indication of a quasi-reversible electron trans-
fer in the electrode reaction.
The voltammograms of L3 compound were investi-
gated under the same experimental conditions (from +
1.5 V to −2.3 V at 100 mVs−1 in Fig. 6c), three
cathodic waves (Ic, IIc, and IIIc at about −1.36, −1.62
and −2.05 V, respectively) and one anodic wave (Ia’ at
about +1.42 V). At higher scan rates (≥ 200 mVs−1) the
oxidation process Ia became more intense (Fig. 7c).
However, at higher scan rates (≥ 400 mVs−1) the IIIc
peak wasn’t observed (Fig. 7c).
It was found that the initial oxidation peak current of L1, L2
and L3 gradually increased and a negative shift in the peak
potential existed with increasing scan rate by using the CVs
(Fig. 7). A plot of logarithm of peak current significantly
correlated with the logarithm of scan rate for all L1, L2 and
L3 with slopes between 0.45, 0,48 and 0.52, respectively
(correlation coefficient between 0.987, 0.976 and
0.991). by using the CV results obtained between 10
and 1,000 mVs−1. These results showed that the redox
processes were predominantly diffusion controlled in the
whole scan rate range studied.
Taking into account the reported data concerning
electrochemical behavior of recently synthesized pyrim-
idine compounds such as 1-amino-5-benzoyl-4 phenyl-
1H-pyrimidine-2-one [27] and 2-iminopyrimidines or 2-
thioxopyrimidine [28], N-(5-benzoyl-2-oxo-4-phenyl-2H-
pyrimidin-1-yl)-oxalamic acid or malonamic acid [29,
30] at hanging mercury drop and glassy carbon elec-
trodes, respectively, the electron-donating groups
lowered the oxidation potentials, while electron-
withdrawing groups had the opposite effect [31] There
was a mechanism involving self-protonation reactions in
the electrochemical reduction of the imine or thio, and car-
bonyl groups in pyrimidines in the 2-iminopyrimidines and 2-
thioxopyrimidine [28].
Functional groups of (C=S) and/or (C=O) are probably
reduced in the compounds. In all these compounds, the
common functional group is imin (C=N) group. If reduc-
tion was over imin (C=N) group which is common in all
compounds, there would not be a distinctive difference
among reduction potentials of three compounds. However,
we think the fact that L1 has more positive reduction
potential can only be explained this way. Furthermore,
L1, L2 and L3 compounds have the same functional
groups. However, since L1 has (C=S) functional group,
in which the sulfur atom is a softer as a difference from
Fig. 6 Cyclic voltammogram of A (L1), B (L2) and C (L3) compounds (1×10−3 M) at 100 mVs−1 scan rate on glassy carbon electrode in DMF/TBAP

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J Fluoresc (2014) 24:389–396
Fig. 7 Cyclic voltammograms of A (L1), B (L2) and C (L3) compounds (1×10−3 M) at on glassy carbon electrode in DMF/TBAP at various
scan rates (10, 25, 50, 100, 200, 400, 600, 800 and 1,000 mVs−1
)
the others, its reduction potential is more positive than
the others.
Synthesis of Schiff Base Ligands
2,6-bis((E)-((5-Benzoyl-2-oxo-4-Phenylpyrimidin-1(2H)-yl)
Imino)Methyl)-4-(Methyl)Phenol (L1)
Experimental
Synthesis and structural characterisations were described
previously [34].
Reagents and General Techniques
All chemicals are commercially available and were used
without further purification. All reagents and solvents were
of reagent grade quality and were obtained from com-
mercial suppliers. All solvents were dried by refluxing
with appropriate drying agents and distilled before use.
The homogeneity of the products was tested in each
step by TLC (SiO2). Ferrocenecarboxaldehyde, 4-t-bu-
tyl-2,6-diformylphenol were purchased from Aldrich
Chem. Co. 1-Amino-5-benzoyl-4-phenyl-1H -pyrimi-
dine-2-thione, 1-Amino-5-benzoyl-4-phenyl-1H-pyrimi-
dine-2-one [32] and 2,6-diformyl-4-methylphenol [33]
were synthesized according to the method described in
literature.
The elemental analyses (C, H, N, S) were performed
by using Leco CHNS model 932 elemental analyzer.
FT-IR spectra were obtained using KBr pellets (4,000–
400 cm−1) on Bio-Rad-Win-IR Spectrophotometer. The
1H NMR and 13C NMR spectra of the Schiff bases
were taken on a Bruker 300 MHz Ultrashield TM
NMR instrument. UV/visible absorption spectra were
recorded with Schimadzu UV-1601 spectrophotometer
(Tokyo, Japan). All fluorescence measurements were
undertaken by using Varian-Carry Eclipse spectrofluorimeter
(Mulgrave, Australia).
2,6-bis((E)-((5-Benzoyl-2-oxo-4-Phenylpyrimidin-1(2H)-yl)
Imino)Methyl)-4-(Tert-Butyl)Phenol (L2)
Synthesis and structural characterisations were described
previously [35].
(2-(((5-Benzoyl-2-oxo-4-Phenylpyrimidin-1(2H)-yl)Imino)
Methyl)Cyclopenta-1,3-Dien-1-yl)(Cyclopenta-1,3-Dien-1-yl)
Iron (L3)
The Schiff base ligand (L3) was prepared by 1:1 condensation
reaction between N-aminopyrimidine-2-one and ferrocene-
carboxaldehyde. Ferrocenecarboxaldehyde (0.214 g, 1 mmol),
N-aminopyrimidine-2-one (0.291 g, 1 mmol) and hot metha-
nol solution (30 mL) containing few drops of HCl were mixed
slowly with a constant stirring (Fig. 1). Then the mixture was
refluxed for 2 h. A red precipitate was formed. The isolated
solid precipitate was filtered off, washed with hot methanol
and diethylether and then dried in vacuum over P2O5. Claret
red, yield was 380 mg (78 %), Mp 215 °C. Anal. Calc. for
C28H21FeN3O2 (487,33 g/mol): C, 69.01; H, 4.34; N, 8.62.
Found: C, 68.77; H, 4.24; N, 8.53 %. Selected IR data (KBr, ν
cm−1): 3064 ν(C–Hpyrimidine), 1643 ν(C=O), 1599 ν(C=
1
N
azomethine). H NMR (300 MHz, CDCl3): δ=8.99 (s, 1H),

J Fluoresc (2014) 24:389–396
395
6. Cleiton M, Da S, Daniel L, da S, Luzia V, Modolo RBA, Maria A,
de R, Cleide VB, Martins A d F (2011) Schiff bases: a short
review of their antimicrobial activities. J Adv Res 2:1–8
7. Khuhawar MY, Mughal MA, Channar AH (2004) Synthesis and
characterization of some new Schiff base polymers. Eur Polymer J
40:805–809
8. Pandeya SN, Srirama D, Nathb G, DeClercq E (1999) Synthesis,
antibacterial, antifungal and anti-HIV activities of Schiff and
Mannich bases derived from isatin derivatives and N-[4-(4′-
chlorophenyl)thiazol-2-yl] thiosemicarbazide. Eur J Pharma Sci
9:25–31
9. Muratov N, Mescheriakov AK (2005) Investigation of anticancer
activity of macrocyclic Schiff bases by means of 4D-QSAR based
on simplex representation of molecular structure. SAR QSAR
Environ Res 16:219–230
10. Casellato U, Vigato PA (1977) Transition metal complexes with
binucleating ligands. Coord Chem Rev 23:31–50
11. Kandil SS, Katib SMA, Yarkandi NHM (2007) Nickel(II),
Palladium(II) and Platinum(II) Complexes of N′-Allyl-N′-
pyrimidin-2-ylthiourea. Trans Met Chem 32:791–798
12. Fahmy HTY, Sherif Rostom SAF, Bekhit AA (2002) Synthesis
and antitumor evaluation of new polysubstituted thiazole and
derived thiazolo[4,5-d] pyrimidine systems. Arch Pharm Pharm
Med Chem 5:213–222
13. Nasr MN, Gineinah MM (2002) Pyrido[2,3-d]pyrimidines and
pyrimido[50,40:5,6]pyrido [2,3-d]pyrimidines as new antiviral
agents: Synthesis and biological activity. Arch Pharm 335:289–295
14. Tozkoparan B, Ertan M, Kelicen P, Demirdamar R (1999) Syn-
thesis and anti-inflammatory activities of some thiazolo[3,2-a]py-
rimidine derivatives. Il Farmaco 54:588–593
15. Amr EA, Ashraf MM, Salwa FM, Nagla AA, Hammam AG (2006)
Anticancer activities of some newly synthesized pyridine, pyrane,
and pyrimidine derivatives. Bioorg Med Chem 14:5481–5488
16. Kumar N, Singh G, Yadav AK (2001) Synthesis of some new
pyrido_2,3-d_pyrimidines and their ribofuranosides as possible
antimicrobial agents. Heteroat Chem 12:52–56
8.48 (s, 1H), 7.80 (d, J=7.4 Hz 2H, ArH), 7.54 (t, J=7.4 Hz,
1H, ArH), 7.45 (t, J=6.6 Hz, 2H, ArH), 7.40–7.33 (m, 5H,
ArH), 4.84 (quasitriplet, J=1.7 Hz, 2H, FerroceneH), 4.68
(quasitriplet, J=1.7 Hz, 2H, FerroceneH), 4.40 (bs, 5H,
FerroceneH) ppm. 13C NMR (75 MHz, DMSO-d6): δ =192.1,
170.9, 170.5, 151.8, 149.2, 137.5, 137.4, 133.8, 131.0, 130.1,
129.1, 129.0, 128.7, 115.7, 75.2, 72.8, 70.3, 69.7 ppm.
Electrochemical Assay
Electrochemical experiments were performed with an
Autolab PGSTAT 128 N potentiostat, (The Netherlands)
using a three electrode system, glassy carbon as a working
electrode (Φ: 3 mm, BAS), platinum wire as an auxiliary
electrode and Ag/AgCl (NaCl 3 M, Model RE-1, BAS,
USA) as a reference electrode. The reference electrode
was separated from the bulk solution by a fritted-glass
bridge filled with the solvent/supporting electrolyte mix-
ture. Before starting each experiment, the glassy carbon
electrode was polished manually with alumina (Φ:
0.01 μm). CV experiments were recorded at room temper-
ature in extra pure DMF, and ionic strength was maintained
at 0.1 mol L−1 with electrochemical grade TBAP as the
supporting electrolyte. Solutions were deoxygenated by a
stream of high purity nitrogen for 10 min prior to the
experiments, and during the experiments nitrogen flow
was maintained over the solution.
Acknowledgments The authors wish to thank Presidency of Scien-
tific Research Projects of University of Yuzuncu Yil (2011-FED-
B009) for the financial support.
17. Mangalagiu G, Ungureanu M, Grosu G, Mangalagiu I, Petrovanu
M (2001) New pyrrolo-pyrimidine derivatives with antifungal or
antibacterial properties. Ann Pharm Fr 59:139–140
18. Viciano-Chumillas M, Tanase S, Aromí G, Smits JMM, de Gelder
R, Solans X, Bouwman E, Reedijk J (2007) Coordination Versa-
tility of 5(3)-(2-Hydroxyphenyl)-3(5)-methylpyrazole: Synthesis,
Crystal Structure and Properties of CoIII, NiII and CuII Complexes.
Eur J Inorg Chem 18:2635–2640
References
1. Taha ZA, Ajlouni AM, Al-Hassan KA, Hijazi AK, Faig AB
(2011) Syntheses, characterization, biological activity and fluores-
cence properties of bis-(salicylaldehyde)-1,3-propylenediimine
Schiff base ligand and its lanthanide complexes. Spectrochim
Acta A 81:317–323
2. Zhou L, Cai P, Feng Y, Cheng J, Xiang H, Liu J (2012) Synthesis
and photophysical properties of water-soluble sulfonato-Salen-
type Schiff bases and their applications of fluorescence sensors
for Cu2+ in water and living cells. Anal Chim Acta 735:96–106
3. Guo D, Wu P, Tan H, Xia L, Zhou W (2011) Synthesis and
luminescence properties of novel 4-(N-carbazole methyl) benzoyl
hydrazone Schiff bases. J Lumin 131:1272–1276
4. Majumder A, Rosair GM, Mallick A, Chattopadhyay N, Mitra S
(2006) Synthesis, structures and fluorescence of nickel, zinc and
cadmium complexes with the N, N, O-tridentate Schiff base N-2-
pyridylmethylidene-2-hydroxy-phenylamine. Polyhedron 25:
1753–1762
5. Basak S, Sen S, Marschner C, Baumgartner J, Batten SR, Turner
DR, Mitra S (2008) Synthesis, crystal structures and fluorescence
properties of two new di- and polynuclear Cd(II) complexes with
N2O donor set of a tridentate Schiff-base ligand. Polyhedron 27:
1193–1200
19. Roy S, Mandal TN, Barik AK, Pal S, Gupta S, Hazra A, Butcher RJ,
Hunter AD, Zeller M, Kar SK (2007) Metal complexes of pyrimidine
derived ligands—Syntheses, characterization and X-ray crystal
structures of Ni(II), Co(III) and Fe(III) complexes of Schiff base
ligands derived from S-methyl/S-benzyl dithiocarbazate and 2-S-
methylmercapto-6-methylpyrimidine-4 carbaldehyde. Polyhedron
26:2603–2611
20. Salih NA (2008) Synthesis and characterization of novel azole
heterocycles based on 2,5-disubstituted thiadiazole. Turk J Chem
32:229–235
21. Roy S, Westmaas JA, Buda F, Reedijk J (2009) Platinum(II)
compounds with chelating ligands based on pyridine and pyrim-
idine: DNA and protein binding studies. J Inorg Biochem 103:
1288–1297
22. Nakamoto K (1997) Infrared spectra and Raman spectra of inorganic
and coordination compounds. John Wiley & Sons, New York
23. Tümer M, Deligönül N, Gölcü A, Akgün E, Dolaz M, Demirelli
H, Dığrak M (2006) Mixed-ligand copper(II) complexes: investi-
gation of their spectroscopic, catalysis, antimicrobial and potenti-
ometric properties. Trans Met Chem 31:1–12
24. Sönmez M, Çelebi M, Berber İ (2010) Synthesis, spectroscopic
and biological studies on the new symmetric Schiff base derived

396
J Fluoresc (2014) 24:389–396
from 2,6-diformyl-4-methylphenol with N-aminopyrimidine. Eur
J Med Chem 45:1935–1940
its Cu(II), Co(II), Mn(II), Ni(II), Zn(II), Cd(II), and Pd(II) com-
plexes: synthesis, characterization, electrochemical properties, and
biological activity. J Coord Chem 63:848–860
25. Huang G, Song Q, Ma Y (2001) Metal complexes of ferrocene-
carboxaldehyde 2,4 dichlorobenzoylhydrazone. Synth React Inorg
Met Org Chem 31:297–302
26. Pal SK, Krishnan A, Das PK, Samuelson AG (2000) Schiff base
linked ferrocenyl complexes for second-order nonlinear optics. J
Organomet Chem 604:248–259
31. Cai T, Xian M, Wang PG (2002) Electrochemical and peroxidase
oxidation study of N′-Hydroxyguanidine derivatives as NO do-
nors. Bioorg Med Chem Lett 12:1507–1510
32. Akçamur Y, Altural B, Sarıpınar E, Kollenz G, Kappe O, Peters K,
Peters E, Schering HJ (1988) A convenient synthesis of functional-
ized 1H-pyrimidine-2-thiones. Heterocycl Chem 25:1419–1422
33. Gagne RR, Spiro CL, Smith TJ, Hamann CA, Thies WR (1981)
Shiemke; A.K. The synthesis, redox properties, and ligand bind-
ing of heterobinuclear transition-metal macrocyclic ligand com-
plexes. Measurement of an apparent delocalization energy in a
mixed-valent copper(I)copper(II) complex. J Am Chem Soc 103:
4073–4081
34. Gülcan M., İspir E, Sönmez M (2012) International Symposium
on Metal Complexes, vol. 2. Lisbon, Portugal.
35. Gülcan M, Çelebi M, Sönmez M (2012) International Symposium
on Metal Complexes, vol. 2. Lisbon, Portugal.
27. Kılıç H, Berkem M (2004) Electrochemical behavior of some new
pyrimidine derivatives. J Serb Chem Soc 69:689–703
28. Akbas E, Levent A, Gümüş S, Sümer MR, Akyazı İ (2010) Synthesis
of some novel pyrimidine derivatives and investigation of their
electrochemical behavior. Bull Korean Chem Soc 31:3632–3638
29. Sönmez M, Çelebi M, Levent A, Berber İ, Şentürk Z (2010) Synthe-
sis, characterization, cyclic voltammetry, and antimicrobial properties
of N-(5-benzoyl 2-oxo-4-phenyl-2H-pyrimidine-1-yl)-malonamic
acid and its metal complexes. J Coord Chem 63:1986–2001
30. Sönmez M, Çelebi M, Levent A, Berber İ, Şentürk Z (2010) A
new pyrimidine-derived ligand, N-pyrimidine oxalamic acid, and