A new 2-((Z)-thiosemicarbazidomethyl)-quinolin-8-YL acetate ligand and its Cu(II) complex: Syntheses, structures, and characterizations

Article abstract of DOI:10.1080/10426507.2012.668987

A new ligand, 2-((Z)-thiosemicarbazidomethyl)-quinolin-8-yl acetate (C ₁₃H₁₂ N₄O₂S) (L) and its Cu(II) coordination complex, [Cu(L₁)] [HL₁ = (Z)-1-((8-hyd- roxyquinolin-2-yl)methylene)thiosemicarbazide], have been synthesized, and characterized by IR, elemental analysis, ¹H NMR, MS, and X-ray single-crystal diffraction. L shows a stable three-dimensional supramolecular structure through hydrogen bonds and - stacking interactions. [Cu(L ₁)] shows a three-dimensional network structure formed only by hydrogen bonds. In addition, the fluorescence spectra of L were measured. Copyright

Full text of DOI:10.1080/10426507.2012.668987

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A New 2-((Z)-Thiosemicarbazidomethyl)-
Quinolin-8-YL Acetate Ligand and its
Cu(II) Complex: Syntheses, Structures,
and Characterizations
Li-juan Wei a , Hong-Ling Gao a & Jian-Zhong Cui a
a Department of Chemistry , Tianjin University , Tianjin , P. R. China
Accepted author version posted online: 02 Mar 2012.Published
online: 19 Jun 2012.
To cite this article: Li-juan Wei , Hong-Ling Gao & Jian-Zhong Cui (2012) A New 2-((Z)-
Thiosemicarbazidomethyl)- Quinolin-8-YL Acetate Ligand and its Cu(II) Complex: Syntheses,
Structures, and Characterizations, Phosphorus, Sulfur, and Silicon and the Related Elements, 187:9,
1101-1108, DOI: 10.1080/10426507.2012.668987
To link to this article: http://dx.doi.org/10.1080/10426507.2012.668987
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Phosphorus, Sulfur, and Silicon, 187:1101–1108, 2012
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2012.668987
A NEW 2-((Z)-THIOSEMICARBAZIDOMETHYL)-
QUINOLIN-8-YL ACETATE LIGAND AND ITS Cu(II)
COMPLEX: SYNTHESES, STRUCTURES, AND
CHARACTERIZATIONS
Li-juan Wei, Hong-Ling Gao, and Jian-Zhong Cui
Department of Chemistry, Tianjin University, Tianjin, P. R. China
GRAPHICAL ABSTRACT
S
N
NH2
Cu(NO3
NH2
O
HN
Cu
N
)
2·3H2O
H2SO4
(AcO)2
N
S
SeO2
NH2NHC(S)NH2
CH3CH2OH
CHO
N
N
H2O,CH2Cl2,
CH3OH
N
CH3
dioxane
O
N
N
OCOCH3
OCOCH3
OH
OCOCH3
1
[Cu(L1)]
2
L
3
Abstract A new ligand, 2-((Z)-thiosemicarbazidomethyl)-quinolin-8-yl acetate (C13H12
N4O2S) (L) and its Cu(II) coordination complex, [Cu(L1)] [HL1 (Z)-1-((8-hyd-
=
roxyquinolin-2-yl)methylene)thiosemicarbazide], have been synthesized, and characterized
by IR, elemental analysis, 1H NMR, MS, and X-ray single-crystal diffraction. L shows a
stable three-dimensional supramolecular structure through hydrogen bonds and π-π stacking
interactions. [Cu(L1)] shows a three-dimensional network structure formed only by hydrogen
bonds. In addition, the fluorescence spectra of L were measured.
Keywords 8-Hydroxyquinoline derivatives; crystal structure; fluorescence property; sulfur
INTRODUCTION
The rational design and synthesis of light-emitting materials have remained an im-
portant research focus in recent years.1–3 As with other typical light-emitting materials,
luminescent coordination compounds are of great interest due to their good performance
in sensor technologies, electro luminescent devices and full-color flat panel displays.4,5
However, there is still a challenge in predicting their structures. Generally, there are various
factors affecting the final structures, including the organic ligands, central metal ions, and
solvent molecules. The selection of the ligand plays a key role because deliberate modifica-
tions on the organic ligands can dramatically influence the ultimate structural topologies of
the coordination solids. 8-hydroxyquinoline derivatives, with high fluorescence quantum
yields, have been used as an object doped in the body of light-emitting materials.6–8 Until
Received 17 December 2011; accepted 16 February 2012.
This work was supported financially by the National Natural Science Foundation of China (No. 21001078)
and the Open Project of Key Lab Adv Energy Mat Chem (Nankai Univ) (KLAEMC-OP201101).
Address correspondence to Hong-ling Gao, Jian-Zhong Cui, Professor, Department of Chemistry, Tianjin
University, Tianjin 300072, P. R. China. E-mail: cuijianzhong@tju.edu.cn; ghl@tju.edu.cn
1101

1102
L.-J. WEI ET AL.
now, the biological activity of sulfur-containing quinoline derivative Schiff base has been
researched in related fields,9,10 however, the research on their optical properties, such as
fluorescence, are few. The variety of possible Schiff-base metal complexes with a wide
choice of ligands, and coordination modes, has prompted us to undertake research in this
area.
In this paper, we report the synthesis and characterization of a new sulfur-containing
Schiff-base ligand 2-((Z)-thiosemicarbazidomethyl) quinolin-8-yl acetate (Scheme 1) and
its new copper (II) coordination complex. In addition, the crystal structures of them and the
luminescent property of L are presented.
S
N
NH2
Cu(NO3)2·3H2
NH2
O
HN
Cu
N
O
H2SO4
N
S
SeO2
NH2NHC(S)NH2
CH CH OH
CHO
N
N
H2O,CH2Cl2,
CH3OH
N
CH3
dioxane
(AcO)2O
N
N
3
2
OCOCH3
OCOCH3
OH
OCOCH3
1
[Cu(L1)]
2
L
3
Scheme 1
RESULTS AND DISCUSSION
The synthetic route of L and coordination complex [Cu(L1)] is outlined in Scheme 1.
All known compounds (2,11,12 311,13) were characterized and the data compared to the
literature.
Spectroscopic Properties
The IR spectrum of L shows two bands at 3406 and 3039 cm−1, which are attributed
to the two stretching frequencies υ(N H). A strong band at 1761 cm−1 is assigned to the
υ(C O) vibration. A strong band at 1591 cm−1 is ascribed to the υ(C N) vibration. The
two bands at 1190 and 1163 cm−1 are attributed to the stretching frequencies υ(C O C). A
weak band at 1532 cm−1 is ascribed to the υ(C S C) vibration. A weak band at 846 cm−1
is ascribed to the υ(C S) vibration. The IR spectra of L are consistent with the structure
of L.
The IR spectrum of [Cu(L1)] has been employed to distinguish the coordination
modes of copper (II) ion. In the IR spectrum, υ(N-H) absorption bands appear at 3422
cm−1. The υ(C N) absorption band appears at 1633 cm−1, which has a 42 cm−1 red shift
compared with 1591 cm−1 in free L, indicating coordination of the C N with copper (II).
The IR spectra of [Cu(L1)] are consistent with the structure of [Cu(L1)].
Crystal Structure
The X-ray crystal structure of L with atomic labeling scheme is shown in Figure 1
(left). The crystal packing of molecules connected by π-π interactions is shown in Figure
S1 (Supplemental materials). As shown in Figure 1, the asymmetric unit contains four
molecules. Several interesting observations can be found about the structure. First, L
is composed of acetoxy group, thiosemicarbazide skeleton and quinoline skeleton. The
length of C N is 1.294(2) Å, C O bond is 1.204(2) Å, C S bond is 1.6822(17) Å. All
the quinoline rings in the molecules show the usual features.

A NEW 2-((Z)-THIOSEMICARBAZIDOMETHYL)-QUINOLIN-8-YL ACETATE LIGAND 1103
Figure 1 3D ORTEP representation of L connected by hydrogen bonds with 30% probability thermal ellipsoids
(A 1 – x, 2 – y, 1 – z; B 2 – x, 0.5 + y, 1.5 – z; C x, 2.5 – y, −0.5 + z).
. . .
The intramolecular hydrogen bonds such as N(3) H(3) N(1) hydrogen bond, is
2.018 Å, 133.1◦ in the molecules structure of L, which makes C11, C12, N2, N3, H3, N1 an
irregular six-membered ring (Figure 1), and makes the six-membered ring and the adjacent
. . .
pyridyl ring almost coplanar. So is the intramolecular hydrogen bond N(4) H(4A) N(2)
bond. It is 2.238 Å, 105.4◦, which makes N3, C13, N4, H4A, N2 an irregular five-membered
ring (Figure 1). The interaction of the two intramolecular hydrogen bonds, makes molecules
1
form a stable cis-configuration, and H3 of N3 and H4A of N4 in H NMR shift to
low-field.
. . .
From Figure 1, the intermolecular hydrogen bond C(9C) H(9C) O(1B), makes
the two molecules connect dislocation in parallel. C(10) H(10) S(1B), contacts the two
molecules vertically. N(4) H(4B) S(1A) connects the adjacent molecules in parallel.
. . .
. . .
The single molecules between each other are connected by hydrogen bonds. The hydro-
gen bonds show three different environments (Figure 1). In the whole structure, there
is a weak face-to-face π-π interaction between the phenyl ring plane with the relative
pyridyl ring plane, so the molecules are packed into layers, indicated by the interplanar
distance of 3.740 Å. Furthermore, the final three-dimensional networks are formed by
intramolecular and intermolecular hydrogen bonds interaction, which further stabilize the
solid three-dimensional supramolecular structure (Figure S1, Table S1, in Supplemental
materials).
The ORTEP representation of [Cu(L1)] of the complex [Cu(L1)] is shown in Figure 2.
Three-dimensional network structure of the complex [Cu(L1)] is shown in Figure S2 (Sup-
plemental materials). Selected bond lengths and angles are presented in Table 2. From
Figure 2 and Table 2 it can be seen that the copper (II) atom is bonded to two N donors,
one O donor, and one S donor of one ligand, displaying a distorted tetrahedral geometry,

1104
L.-J. WEI ET AL.
Figure 2 ORTEP representation of [Cu(L1)] showing the molecular structure with 30% probability thermal
ellipsoids.
and a methanol molecule is uncoordinated to copper (II) atom in the complex. The distance
of the copper(II) ion and the bridging sulfur atom is 2.439(3) Å, which is longer than
the bond lengths of Cu(1) N(1), Cu(1) N(3) and Cu(1) O(1) [Cu(1) N(1) = 1.943(5)
Å, Cu(1) N(3) = 1.889(5) Å, Cu(1) O(1) = 1.956(4) Å]. The bite angles formed by the
donor-metal-donor at the metal center [N(3) Cu(1) N(1), 89.19(18)◦; N(3) Cu(1) S(1),
156.63(14)◦; N(1) Cu(1) O(1), 85.15(17)◦; O(1) Cu(1) S(1), 114.85(11)◦], which is
larger or smaller than the right angle (90◦) of a normal tetrahedron, indicating a rather dis-
tored tetrahedral coordination geometry around copper (II). As expected the six-membered
ring (N1 C8 C10 N2 N3 Cu1) is coplanar with the largest deviation from the plane
being 0.0207 Å, inclined at 2.2◦ to the quinolinone fused ring. The five-membered ring
(C1 C9 N1 Cu1 O1) and four-membered ring (C11 N3 Cu1 S1) are similar to the
six-membered ring above. In addition, the complex was linked to the methanol molecules by
. . .
. . .
. . .
hydrogen bonds [N(4) H(4A) O(2), N(4) H(4B) O(1)#2, O(2) H(2A) O(1)#1]
and formed a three-dimensional networks supramolecular structure (Figure S2, Table S2,
Supplemental materials).
Luminescent Property
The fluorescence of 1, 2, 3, and L from solutions dissolved in methanol is shown in
Figure 3; the fluorescence of 1, 2, 3, and L from solutions dissolved in DMF is shown in
Figure 4.
Luminescent properties of compounds 1, 2, 3, and L were measured in methanol
(1.0 × 10−5 mol·L−1) at room temperature (Figure 3). Upon the excitation of ultraviolet
light, the emission peaks of 1 at 580 nm, 2 at 579 nm, and 3 at 581 nm, give yellow
fluorescence,14 the emission peaks of L at 488 nm, which gives an intense blue luminescence
in methanol.14 The result shows that the luminescence wavelength of L shifts to blue when
compared with 1, 2, and 3 (π-π interaction and hydrogen bonds interaction in L).
1, 2, 3, and L have been dissolved in DMF (1.0 × 10−5 mol·L−1) at room temperature
(Figure 4). Upon the excitation of ultraviolet light, the emission peaks of 1 at 569 nm, 2 at

A NEW 2-((Z)-THIOSEMICARBAZIDOMETHYL)-QUINOLIN-8-YL ACETATE LIGAND 1105
Table 1 Crystal data and structure refinement parameters for L and [Cu(L1)]
L
[Cu(L1)]
Cu(C12H12N4O2S)
339.86
Empirical formula
Formula weight
C13H12N4O2S
288.34
Temperature/K
Wavelength/Å
123.3(2) K
0.71073
113(2)
0.71073
Crystal system, space group
Unit cell dimensions
monoclinic, P21/c
monoclinic, P21/c
a = 9.600(13) Å; α = 90◦
b = 7.628(10) Å; β =
97.90(3)◦
a = 7.9910(2) Å; α = 90◦
b = 9.3310(3) Å; β = 112.516(2)◦
c = 19.5537(5) Å; γ = 90◦
V = 1346.86(6)
4, 1.422
0.247
600
2.46◦–25.01◦
c = 18.26(2) Å; γ = 90◦
Volume/Å3
V = 1324(3)
Z, Calculated density/(Mg/m3)
Absorption coefficient/mm−1
F(000)
4, 1.704
1.812
692
2.46◦– 25.01◦
θ range for data collection
Limiting indices
−9 ꢀ h ꢀ 8, −10 ꢀ k ꢀ 11,
−11 ≤ h ≤ 11, −8 ≤ k ≤ 9,
−14ꢀlꢀ23
−20 ≤l ≤ 21
Reflections collected/unique
Completeness to θ
Refinement method
Data/restraints/parameters
Goodness-of-fit on F2
4900/2375 [R(int) = 0.0186]
100.0%
10255/2336 [R(int) = 0.1154]
100.00%
Full-matrix least-squares on F2
2375/0/193
Full-matrix least-squares on F2
2336/3/191
0.806
1.054
Final R indices [I > 2σ(I)]
R indices (all data)
Largest diff. peak and hole/(e/nm3)
R1 = 0.0323, wR2 = 0.0875
R1 = 0.0376, wR2 = 0.0941
219 and −226
R1 = 0.0670, wR2 = 0.1221
R1 = 0.0853, wR2 = 0.1332
552 and −693
568 nm, and 3 at 570 nm, give yellow fluorescence.14 The emission peaks of L at 475 nm,
gives an intense blue luminescence in DMF,14 a little shifted toward blue compared to 1, 2,
3, and L dissolved in methanol, which indicated that solvent slightly affects the emission
peak wavelength.
Table 2 Selected bond lengths (Å) and angles (◦) for L and [Cu(L1)]
L
S(1)–C(13)
O(2)–C(2)
O(2)–C(3)
N(1)–C(11)
N(1)–C(8)
C(6)–C(5)
C(4)–C(5)
C(2)–O(2)–C(3)
C(11)–N(11)–C(8)
C(13)–N(3)–N(2)
1.6822(17)
1.368(2)
1.404(2)
1.333(2)
1.366(2)
1.362(3)
1.414(3)
116.84(13)
117.50(13)
118.45(14)
O(1)–C(2)
N(4)–C(13)
N(2)–C(12)
C(7)–C(9)
C(7)–C(6)
C(9)–C(10)
C(3)–C(8)
N(2)–C(12)–C(11)
N(4)–C(13)–N(3)
C(4)–C(3)–O(2)
1.204(2)
1.324(2)
1.294(2)
1.411(2)
1.420(2)
1.360(2)
1.420(2)
130.05(16)
116.48(15)
118.16(16)
N(3)–C(13)
N(3)–N(2)
C(1)–C(2)
C(7)–C(8)
C(12)–C(11)
C(4)–C(3)
C(11)–C(10)
O(1)-C(2)-C(1)
O(2)–C(2)–C(1)
N(3)–C(13)–S(1)
1.360(2)
1.368(2)
1.494(3)
1.429(2)
1.470(2)
1.361(2)
1.417(2)
126.21(18)
111.24(16)
119.15(12)
[Cu(L1)]
N(3)–Cu(1)–N(1)
N(3)–Cu(1)–O(1)
N(1)–Cu(1)–O(1)
N(3)–Cu(1)–S(1)
Cu(1)–N(3)
Cu(1)–N(1)
Cu(1)–O(1)
Cu(1)–S(1)
1.889(5)
1.943(5)
1.956(4)
2.439(3)
89.19(18)
172.64(15)
85.15(17)
69.77(13)
N(1)–Cu(1)–S(1)
O(1)–Cu(1)–S(1)
156.63(14)
114.85(11)

1106
L.-J. WEI ET AL.
Figure 3 The fluorescence of the four compounds (1, 2, 3, and L) in methanol.
EXPERIMENTAL
Material and Methods
All the chemicals were obtained from commercial sources or prepared according to
standard methods. Melting point was measured by an X4 Melting-Point Apparatus with
a microscope and uncorrected. Elemental analysis was performed by a Perkin–Elmer 240
Figure 4 The fluorescence of the four compounds (1, 2, 3, and L) in DMF.

A NEW 2-((Z)-THIOSEMICARBAZIDOMETHYL)-QUINOLIN-8-YL ACETATE LIGAND 1107
1
elementary analysis instrument. The H NMR (500 and 400 MHz) was recorded on the
Bruker AM-500 and Bruker AM-400 spectrometer. Chemical shifts (δ) are reported relative
to TMS (1H). IR spectra were recorded on a BIO-RAD FTS 3000. Mass spectra (ESI) were
obtained on a Finnegan LCQ Advantage MAX spectrometer. Photoluminescence spectra
were measured by a Cary Eclipse fluorescence spectrophotometer with a xenon arc lamp
as the light source. The Supplemental materials contains additional synthetic procedures
and 1H NMR spectra for 2, 3, and L (Figures S3–S6). Compounds 2 and 3 were prepared
according to reported procedures.11,12
Synthesis of the 2-((Z)-Thiosemicarbazidomethyl)-Quinolin-8-yl
Acetate (L)
An ethanolic solution (40 mL) of 2-formylquinolin-8-yl acetate (6 mmol, 1.29 g)
was added drop by drop to the solution of thiosemicarbazide (6 mmol, 0.546 g) in ethanol
(60 mL). The resulting mixture was refluxed for 4 h. The volume of solvent was reduced
to 10 mL and the yellow precipitate was collected with filtration, washed with hot ethanol,
then diethylether, the residue was recrystallized from the mixture of ethanol and acetone
(2:1 v:v), and gave 1.2 g of yellow crystals L. Yield, 69%; M.p: 203.6–204.8 ◦C; IR (KBr):
3406 (N H), 3039, 1761 (C O), 1591 (C N), 1532 (C S C), 1190, 1163 (C O C),
1
846(C S) cm−1; H NMR (DMSO-d6, 500 MHz): δ = 13.95 (s, 1H, NH), 8.76 (s, 1H,
NH), 8.66 (dd, J1 = 8.3, J2 = 3.8 Hz, 1H), 8.42 (s, 1H), 7.96 (d, J = 8.1 Hz, 1H), 7.90 (dd,
J1 = 8.6, J2 = 2.5 Hz, 1H), 7.73 (t, J = 7.8 Hz, 1H), 7.67 (d, J = 7.5 Hz, 1H),7.60(s, 1H,
CH), 2.67 (s, 3H, CH3); 1H NMR (DMSO-d6, D2O, 500 MHz): δ = 8.61 (d, J1 = 8.6 Hz,
1H), 8.42 (s, 1H), 7.94 (dd, J1 = 8.2, J2 = 1.1 Hz, 1H), 7.84 (dd, J = 8.6 Hz, 1H), 7.71
(t, J = 7.9 Hz, 1H), 7.64 (dd, J1 = 7.6, J2 = 1.2 Hz, 1H), 7.57 (s, 1H, CH), 2.63 (s, 3H,
CH3); ESI-MS m/z(%): 311.1 [M + Na]+ (100%); Anal. Calcd (%) for C13H12N4O2S: C,
54.15; H, 4.20; N, 19.43; S, 11.12. found (%): C, 54.19; H, 4.23; N, 19.51; S, 11.16.
Preparation of the Complex [Cu(L1)]
Dichloromethane (3 mL) was added drop by drop to a solution of Cu(NO3)2·3H2O
(3.65 mg, 0.0151 mmol) in H2O (2 mL), and then, a solution of L (4.34 mg, 0.0151 mmol)
in CH3OH (4 mL) was added. After keeping the solution at room temperature for one week,
black crystals were obtained by slow evaporation. IR (KBr): 3422(NH), 1633(C N), 1488,
1445, 1387, 1336, 1075(C O), 531(Cu O). Anal. Calcd (%) for [Cu(L1)]: C, 42.41; H,
3.56; N, 16.49; S, 9.43. found (%): C, 42.79; H, 3.32; N, 16.40; S, 9.52.
X-Ray Diffraction
A yellow crystal of L with dimensions of 0.20 mm × 0.20 mm × 0.20 mm was
selected for single-crystal X-ray diffraction measurements preformed on a Super Nova de-
tector. A black crystal of [Cu(L1)] with dimensions of 0.20 mm × 0.18 mm × 0.12 mm was
selected for single-crystal X-ray diffraction measurements preformed on Rigaku Saturn724
CCD detector. The data of L and [Cu(L1)] were collected with graphite-monochromatic
Mo Ka radiation wavelength of 0.71073 Å using the ω/2θ scan technique. Lorentz polariza-
tion and absorption corrections were applied. The structure was solved by direct methods
and refined with a full-matrix least-square technique based on F2 using the SHELXS-9715

1108
L.-J. WEI ET AL.
and SHELXL-9716 programs. Anisotropic thermal parameters were assigned to all non-
hydrogen atoms. All hydrogen atoms were generated geometrically. The crystal data and
structure refinement details for C13H12N4O2S (L) and [Cu(L1)] are summarized in Table
1, and selected bond distances and angles are listed in Table 2. Hydrogen bond lengths and
angles are located in Tables S1 and S2 (Supplemental materials).
Crystallographic data (CIF) for the structure reported in this article has been deposited
in the Cambridge Crystallographic Data Centre as supplementary materials, CCDC No:
844459 for L; 860610 for [Cu(L1)]. Copies of the data can be obtained, free of charge, on
application to the CCDC, 12 Union Road, Cambridge CB12EZ, UK (Fax: ++44(1223)
336-033; email:deposit@ccdc.cam.ac.uk).
CONCLUSION
A new Schiff base 2-(thiosemicarbazide methyl) quinolin-8-yl acetate (L) and its
Cu(II) complex [Cu(L1)], have been synthesized and characterized. The stable three-
dimensional supramolecular structures of them were formed through intermolecular hy-
drogen bonds and/or π-π interactions between the molecules. From the data, figures and
reference, it is said that L has a blue fluorescent emission at 488 in methanol and 475 nm
in DMF solution at room temperature. If it coordinates with metals as the ligand, more
light-emitting materials can be developed.17
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