Hydrogen bonded supramolecular framework in inorganic-organic hybrid compounds: Syntheses, crystal structures, and photoluminescent properties

Article abstract of DOI:10.1080/15533174.2013.791844

Two novel compounds [Zn(bip)(BDC)] (1) and [Co(bip)₂Cl ₂· 4H₂O] (2) [bip = 2-(4-bromophenyl)-1H-imidazo[4, 5-f][1,10]phe- nanthroline, BDC = phthalate acid] have been synthesized by hydrothermal reactions and characterized

Full text of DOI:10.1080/15533174.2013.791844

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Hydrogen Bonded Supramolecular Framework in
Inorganic-Organic Hybrid Compounds: Syntheses,
Crystal Structures, and Photoluminescent Properties
Li Yan a , Yufei Xiao a , Chuanbi Li a , Meiling Liu a , Wenyu Li a & Nan Yang a
a College of Chemistry , Jilin Normal University , Siping , P. R. China
Accepted author version posted online: 25 Nov 2013.Published online: 25 Feb 2014.
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To cite this article: Li Yan , Yufei Xiao , Chuanbi Li , Meiling Liu , Wenyu Li & Nan Yang (2014) Hydrogen Bonded
Supramolecular Framework in Inorganic-Organic Hybrid Compounds: Syntheses, Crystal Structures, and Photoluminescent
Properties, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:6, 829-835, DOI:
10.1080/15533174.2013.791844
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:829–835, 2014
Copyright ꢀ Taylor & Francis Group, LLC
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ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2013.791844
Hydrogen Bonded Supramolecular Framework in
Inorganic-Organic Hybrid Compounds: Syntheses, Crystal
Structures, and Photoluminescent Properties
Li Yan, Yufei Xiao, Chuanbi Li, Meiling Liu, Wenyu Li, and Nan Yang
College of Chemistry, Jilin Normal University, Siping, P. R. China
conditions such as solvent, temperature, pH value and crystal-
lization process.[7,8] In reported MOFs, N-heterocyclic ligands,
such as 2,2ꢁ-bipyridine, 4,4ꢁ-bipyridine, 1,10-phenanthroline,
and their substituted derivatives played an important role in
the rational design to obtain anticipant structures and desired
properties. Our strategy of rational design and synthesis of
coordination polymers is to employ a new designed long-
conjugated unsymmetrical ligand bip (2-(4-bromophenyl)-1H-
imidazo[4,5-f][1,10]phenanthroline) (as shown in Scheme 1): in
view of the following characteristics, (a) it possesses extended
long-conjugated unsymmetrical aromatic system to provide
supramolecular interactions; (b) it has two chelating nitrogen
atoms, which is similar with 2,2’-bipyridyl-like bidentate chelat-
ing ligands; and (c) it possesses strong and rigidity of coordina-
tion ability to metal atoms to construct intriguing structures.[9]
For the past several years, we have worked on the synthesis
of N-heterocyclic compounds.[10–12] However, the investigation
for this type of ligands is not enough. Based on the previous
Two novel compounds [Zn(bip)(BDC)] (1) and [Co(bip)2Cl2·
4H2O] (2) [bip = 2-(4-bromophenyl)-1H-imidazo[4,5-f][1,10]phe-
nanthroline, BDC = phthalate acid] have been synthesized by
hydrothermal reactions and characterized by elemental analy-
sis, thermogravimetric (TG) analysis, infrared spectrum (IR), and
single-crystal X-ray diffraction. Single-crystal X-ray diffraction
reveals that compounds 1 and 2 are zero-dimensional (0D) archi-
tecture, and the existence of hydrogen bonds and π-π interactions
lead the 0D to 2D novel frameworks. Hydrogen bonds and π-π
interactions are powerful interactions for directing supramolecu-
lar architectures. TG analysis shows clear courses of weight loss,
which corresponds to the decomposition of different ligands. The
luminescent properties for the ligand bip and compounds 1–2 are
also discussed.
Keywords crystal structures, fluorescence, thermal stability analysis
INTRODUCTION
During the past decades, metal–organic frameworks (MOFs) reasons, we design and synthesize of the polymers, namely:
are of enormous interest because of their potential applications [Zn(bip)(BDC)] 1 and [Co(bip)2Cl2·4H2O] 2. Compounds 1
in gas storage, separation, catalysis, nonlinear optics and so and 2 exhibit zero-dimensional (0D) structures, and display 2D
on.[1–6] Nowadays, the method of hydrothermal synthesis is layer structures via hydrogen bonds and interchain π-π stacking
widely used to synthesis novel crystal structures, because it interactions. The research shows that 1 and 2 are luminescent
can solve the problems of ligands solubility and enhance the material.
reactivity of reactants in the crystallization process to obtain
perfect crystal. However, it is still a great challenge to rationally
prepare and predict the exact structures and composition of tar-
EXPERIMENTAL
Materials
get products in crystal engineering, because the supramolecular
structures are dependent on a number of parameters such as the
nature of the metal-ligand bonds, coordination geometries of
the metal centers, the ligating topologies of the ligands used,
the metal-ligand ratio, the counterions and the experimental
The ligand bip was prepared according to the description in
the literature procedures.[13] The metallic salt, BDC, and NaOH
were purchased commercially and used without further purifi-
cation.
Physical Measurements
The FT-IR spectrum was measured with KBr pellets in the
range of 4000–400 cm–1 on a Perkin-Elmer 240C spectrom-
eter. TGA (thermogravimetric analysis) was performed using
a Perkin-Elmer TG-7 analyzer at the rate of 10◦C/min rise of
temperature in nitrogen atmosphere. Crystal structures were de-
termined on a Bruker SMART APEX II CCD X-ray diffrac-
tometer. Carbon, hydrogen and nitrogen elemental analyses
Received 9 March 2013; accepted 27 March 2013.
Address correspondence to Li Yan, College of Chemistry,
Jilin Normal University, Siping 136000, P. R. China. E-mail:
yanli820618@163.com
Color versions of one or more of the figures in the article can be
found online at www.tandfonline.com/lsrt.
829

830
L. YAN ET AL.
SCH. 1. The synthesis of bip.
were performed with a PE-2400 elemental analyzer. X-ray pow- applied using multi-scan technique and all the structures were
der diffraction (XRD) measurements were performed using an solved by direct methods with SHELXS-97[14] and refined with
X’pert diffractometer of Philips with monochromated Co-Kα SHELXL-97[15] by full-matrix least-squares techniques on F2.
radiation.
Non-hydrogen atoms were refined with anisotropic temperature
parameters. Experimental details for crystallographic data and
structure refinement parameters for 1 and 2 are listed in Table 1.
Syntheses of 1–2
Synthesis of [Zn(bip)(BDC)] (1)
A mixture of ZnCl2 (0.082 g, 0.3 mmol), bip (0.112 g,
0.3 mmol), BDC (0.100 g, 0.6 mmol) and H2O (18 mL) was
stirred at room temperature and adjusted the pH value to about
7.0 with NaOH. We put the cloudy solution into a 30-mL Teflon-
lined stainless vessel under autogenous pressure at 443 K for
72 h, and afterwards cooled to room temperature at a rate of
RESULTS AND DISCUSSION
Description of Crystal Structures
[Zn(bip)(BDC)2] (1)
The molecular structure of compound 1 is shown in Figure 1.
5◦C/ h. The yellow crystals of compound 1 were collected in The 1D chain structure linked hydrogen bonds is suggested in
80% yield based on Zn. C54H30Br2N8O8Zn2: Anal. Calcd. (%): Figure 2, and the 2D layer structure linked hydrogen bonds is
C 53.62, H 2.50, N 9.26; Found: C 53.55, H 2.39, N 9.41%. IR suggested in Figure 3. Selected important bond lengths and bond
(KBr, cm–1): 1605(vs), 1566(vs), 1453(m), 1389(vs), 1061(s), angles are given in Table 2.
991(s), 837(m), 732(m), 538(m), 439(m).
As shown in Figure 1, the asymmetric unit contains two Zn
(II) atoms, two bip ligands, and two BDC ligands. The Zn (II)
atom is penta-coordinated with three carboxylate oxygen atoms
(O(3), O(4) from one chelating BDC ligand, O(1) from another
bridging BDC ligand) and two nitrogen atoms donors (N(1),
N(2) from one chelating bip ligand).
The bond distances of Zn–O in compound 1 are from 1.958(5)
to 2.373(6) Å, and those of Zn–N bond distances fall in the
2.069(5) to 2.084(6) Å range, which are similar with the val-
ues reported.[16–23] The N(O)–Zn–O(N) angles range are from
87.2(2) to 149.1(2)◦.
As showed in the Figure 1, the BDC ligand coordinates
to two Zn (II) ions through three carboxylic oxygen atoms
in mono-bridging and bidentate chelating fashion, which give
rise to a 0D structure. It is interesting that in the unit of com-
pound 1, 14-membered ring is formed, in which the angle of
Synthesis of [Co(bip)2Cl2·4H2O] (2)
A mixture of CoCl2 (0.114 g, 0.3 mmol), bip (0.112 g,
0.3 mmol), and H2O (18 mL) was stirred at room tempera-
ture and adjusted the pH value to about 7.0 with NaOH. We put
the cloudy solution into a 30-mL Teflon-lined stainless vessel
under autogenous pressure at 443 K for 72 h, and afterwards
cooled to room temperature at a rate of 5◦C/ h. Small red crys-
tals of compound 2 were collected in 85% yield based on Co.
C19H15BrClCo0.50N4O2: Anal. Calcd. (%) C 47.92, H 3.17, N
11.76; Found: C 48.05, H 3.36, N 11.52%. IR (KBr, cm–1):
3372(s), 1701(s), 1605(s), 1459(s), 1277(s), 837(s), 725(s),
656(m), 580(m), 439(m).
X-Ray Crystallography
Single-crystal X-ray diffraction data were collected at room O(1)–Zn(1)–O(4) is 104.392◦; N-heterocyclic ligands bip are
temperature with a Bruker SMART APEX II CCD diffractome- attached to both sides of this chain regularly, and the ligands on
ter equipped with a graphite-monochromatized MoKα radiation the same side are parallel nearly.
(λ = 0.71073 Å) at 293(2) K in the range of 1.67 ≤ θ ≤ 25.67◦
Hydrogen bonding interactions are usually important in
for 1 and 1.46 ≤ θ ≤ 25.05◦ for 2. Absorption corrections were the synthesis of supramolecular architectures, and the most

TWO COMPOUNDS: STRUCTURES AND PROPERTIES
831
TABLE 1
Crystal data and details of structure refinement parameters for
1 and 2
1
2
Empirical formula
C54H30Br2N8O8Zn2 C19H15BrCl
Cot0.50N4O2
Formula weight
Crystal system
Space group
a (nm)
1209.42
monoclinic
C2/c
1.57481(1)
2.4457(3)
1.39872(1)
119.783(2)
4.6756(8)
4
476.18
orthorhombic
Pbcn
1.47427(11)
0.89536(7)
2.7832(2)
90
3.6738(5)
8
1.722
b (nm)
c (nm)
β (◦)
Volume (nm3)
Z
Density (Mg/m3)
(calcd.)
1.718
Absorption
coefficient (mm–1)
F(000)
2.804
2.843
FIG. 1. The molecular structure of compound 1 (hydrogen atoms were omit-
ted).
2416
0.43 × 0.35 ×
0.30
1.67–25.07
12506
1908
0.54 × 0.42
× 0.32
Crystal size (mm3)
as illustrated in Figure 3. The two parallel bip ligands in the
same side recognize each other through aromatic π-π stacking
interaction with the face-to-face distance being 3.499 Å.[9]
Theta range (◦)
Reflections collected
Unique reflections
[Rint]
1.46–25.05
20427
4136 [0.0758]
3263
[0.0624]
1.002
[Co(bip)2Cl2·4H2O] (2)
Goodness-of-fit on
0.987
F2
The molecular structure is shown in Figure 4, and the 2D
layer structure linked hydrogen bonds is suggested in Figure 5.
Selected important bond lengths and bond angles are also listed
in Table 2.
Final R indices [I2σ
(I)]
R1 = 0.0618
wR2 = 0.1293
R1 = 0.1414
wR2 = 0.1604
1.089, –0.746
R1 =
0.0371
wR2 =
0.0880
R1 =
As shown in Figure 4, the asymmetric unit of compound
2 consists of half Co (II) atom, one bip ligand, one chloride
ion, and one lattice water molecule. The coordinated chlo-
ride ions occupy two coordination points of Co (II) atom,
and the Co atom is on a special position. The Co (II) atom
is hexa-coordinated with four nitrogen atoms from two chelat-
ing bip ligands and two chloride ions from metal salts, fur-
nishing a slightly distorted octahedral geometry. The angle of
N(1)–Co(1)–N(2), N(2)–Co(1)–Cl(1A), Cl(1A)–Co(1)–N(2A)
and N(2A)–Co(1)–N(1) is 76.98◦, 92.34◦, 99.41◦, and 91.31◦,
R indices (all data)
0.0566
wR2 =
0.0964
0.472,
–0.446
Largest difference
peak and hole (e.
Å−3
)
interesting aspect of the structure in 1 concerns the intermolec- and the sum is 360.04◦(A: –x – 1, y, –z + 3/2). For the coor-
ular N–H···O interactions. Every pair of molecules linked by in- dination environment of Co(1), the Co(1), N1, N2, N2A, Cl1A
termolecular N3–H3A···O2 hydrogen bonding. The existence of atoms define the basal plane, and the N1A, Cl1A atoms occupy
N3–H3A···O2 hydrogen bonds interactions [H3A···O2 = 1.90 the apical axial positions. The bond distance of Co–Cl in com-
Å, N3···O2 = 2.743(8) Å and N3–H3A···O2 = 168◦] lead the pound 2 is 2.4715 Å, and those of Co–N bond distance fall in
0D zigzag chain to 1D chain infinite structure. It is interesting the 2.150 to 2.165Å range, which are similar with the values
that in the unit of compound 1, 18-membered rings are formed reported.[24–27]
using N3–H3A···O2 hydrogen bonds interactions, and these two
Hydrogen bonding interactions are usually important in the
types of rings (14-membered ring and 18-membered ring) ar- synthesis of supramolecular architectures, there are six type
ranged alternately in the chain structure (see Figure 2). There of hydrogen bonding interactions in compound 2: N–H···Cl,
is another type of Hydrogen bonding interaction C–H···O in- C–H···Br, C–H···Cl, C–H···O, and the most interesting aspect
teraction, which expand 1D chain structure to 2D framework, of the structure in 2 concerns the intermolecular C–H···Cl

832
L. YAN ET AL.
FIG. 2. 1D chain structure linked by N–H···O hydrogen bonds of compound 1 (hydrogen atoms were omitted) (a), two types of rings in the chain structure(b).
The Zn (II) atom is penta-coordinated with three carboxylate
oxygen atoms and two nitrogen atoms donors, forming distorted
[H(8A)···Cl(1) = 2.70 Å, C(8)···Cl(1) = 3.587 Å and
C(8)–H(8A)···Cl(1) = 159◦] interactions, which help in the con-
tetrahedron in the compound 1. Zn (II) metal exhibits four-,
penta-, or six-coordinated mode, especially for four- and six-
coordinated modes are common.[28,29] The most interesting as-
pect of the structure in 1 concerns the intermolecular of H-bond
interactions, which formed two types of rings (14-membered
ring and 18-membered ring) alternately in the chain structure.
The coordination environment around Co(II) center in 2 is in
a distorted octahedral geometry, surrounded by four N atoms
struction of the 2D layer structure (Figure 5). Moreover, there are
π-π interactions between the aryl ring of bip ligands and sym-
metry of the two adjacent equivalent of aromatic ring (symmetry
codes: –x, –1 + y, 1.5 – z, 0.5+x, –1.5 + y, 1.5 – z). The distance
between cg(1)→cg(2) ring centroid is 3.628 Å and cg(3)→cg(4)
is 3.669 Å.[9] Cg(1):C14→C15→C16→C17→C18→C19,
Cg(2): C1→C2→C3→C4→C11→N1(),Cg(3): C4→C5→
C6→C7→C11→C12,y Cg(4): C5→C6→C13→N3→N4.
FIG. 3. 2D layer structure of compound 1 linked by N–H···O and C–H···O hydrogen bonds (dotted lines represent hydrogen bonds).

TWO COMPOUNDS: STRUCTURES AND PROPERTIES
833
odentately coordinated with Zn (II) atoms.[30] In compound 2,
the infrared spectrum exhibited absorption at 3372 cm–1, which
is assigned to O–H stretching vibration.[31] The spectrum of
compound 2 shows the strong bands at 1459 and 837 cm–1 are
due to C=C and C=N stretching vibrations of the coordinated
phenanthroline molecules. Below 700 cm–1 it seems to be a lot
of bands, which correspond to the Co–N stretching mode. The
IR results are good agreement with their solid structural features
from the results of their crystal structures.
XRD Spectra
The simulated and experimental power XRD patterns of 1
and 2 are shown in Figure 6. The patterns calculated from the
single-crystal X-ray data of 1 and 2 are in good agreement with
the observed ones in almost identical peak position but with
different peak intensities, which indicates the phase purity of
the products. The differences in intensity may be due to the
preferred orientation of the powder samples.[32,33]
FIG. 4. The molecular structure of compound 2 (hydrogen atoms were omit-
ted).
from two bip ligands and two terminal Cl atoms. The structures
of coordinated chloride ions in 2 are symmetric.
Thermal Analysis
To examine the stability of compounds 1 and 2, we exam-
ined the TG curves of crystalline samples in the flowing nitro-
IR Spectra
In compound 1, the two peaks at 1605 and 1566 cm–1 cor- gen atmosphere at a heating rate of 10◦C/min (Figure 7). As
respond to the antisymmetric stretching vibrations of carboxyl, expected, in compound 1, the first weight loss corresponding
and 1389 cm–1 correspond to the symmetric stretching vibra- to the removal of lattice BDC is 24.50% (calcd. 27.48%) from
tion of carboxyl. The ꢀv (vas(COO–)-vs(COO–)) are 216 and 137 to 451◦C. The second weight loss of 65.10% from 451 to
177 cm–1, indicating that the carboxyls are bidentately and mon- 651◦C corresponds to the loss of bip ligands (calcd. 62.03%). In
FIG. 5. 2D layer structure of compound 2 linked by C–H···Cl hydrogen bonds (dotted lines represent hydrogen bonds).

834
L. YAN ET AL.
TABLE 2
Selected bond lengths (Å) and bond angles (◦) for compounds
1 and 2
1/
Bond
Dist.
Bond
Dist.
Zn(1)–O(1)
Zn(1)–O(4)
Zn(1)–N(2)
Angle
1.958(5)
2.373(6)
2.069(5)
(◦)
Zn(1)–O(3)
Zn(1)–N(1)
2.031(5)
2.084(6)
Angle
(◦)
O(1)–Zn(1)–O(3)
O(1)–Zn(1)–O(4)
O(3)–Zn(1)–N(1)
N(1)–Zn(1)–O(4)
O(3)–Zn(1)–N(2)
103.1(2) O(3)–Zn(1)–O(4) 59.3(2)
104.42(1) O(1)–Zn(1)–N(1) 106.1(2)
108.4(2) N(2)–Zn(1)–O(4) 87.2(2)
149.1(2) O(1)–Zn(1)–N(2) 122.7(2)
129.3(2) N(2)–Zn(1)–N(1) 80.4(2)
2
Co(1)–N(1)
Co(1)–Cl(1)
Angle
2.165(3)
2.4715(1)
(◦)
Co(1)–N(2)
2.150(3)
Angle
(◦)
N(2)#1–Co(1)–N(2) 163.30(17) N(2)–Co(1)–N(1) 76.98(12)
N(2)#1–Co(1)–N(1) 91.31(12) N(1)#1–Co(1)–N(1) 91.64(17)
N(1)–Co(1)–Cl(1)
89.91(9) N(2)–Co(1)–Cl(1) 99.41(9)
N(1)#1–Co(1)–Cl(1) 169.24(8) N(2)–Co(1)–Cl(1)#1 92.34(9)
Cl(1)#1–Co(1)–Cl(1) 90.55(5)
Symmetry transformations used to generate equivalent atoms: (2)
#1 –x – 1, y, –z + 3/2.
compound 2, the first weight loss of 16.50% corresponds to the
loss of chloride ions and two water molecules (calcd. 15.01%).
The second weight loss in the temperature range of 245–595◦C
can be ascribed to the release of bip ligands (obsvd. 76.50%,
calcd. 78.77%).
FIG. 6. Experimental and simulated X-ray powder diffraction patterns of 1
(a) and 2 (b).
Photoluminescent Properties
In this study, we research the luminescence of compounds 1
and 2, as well as the free ligand bip (Figure 8). The free ligand
exhibits emission at 579 nm (excitation at 325 nm) for bip.
Compound 1 shows one broad emission band with the maximum
intensity at 495 nm upon excitation at 280 nm, which is blue-
shifted by 84 nm relative to the emission wavelength of free
ligand bip. Compound 2 exhibits one broad strong emission
band with the maximum intensity at 395 nm upon excitation
at 247 nm, which is blue-shifted by 184 nm relative to the
emission wavelength of free ligand bip. It is electronic that
the blue-shifted emission of 1 and 2 originated from the π-π∗
electronic transition of bip ligand.[34] It is worth to mention that
luminescent intensity of compounds 1 and 2 is weaker than
the ligand bip. The reason for that is probably attributed to the
quenching effect.[35] The coordination polymers 1 and 2 may be
good candidate for potential photoluminescence material.
FIG. 7. TG curves of compounds 1 and 2.

TWO COMPOUNDS: STRUCTURES AND PROPERTIES
835
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FUNDING
The authors thank the National Natural Science Foundation
of China (No. 20971019) and the Postdoctoral Science founda-
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SUPPLEMENTAL MATERIALS
CCDC 894755 and 894754 contain the supplementary crys-
tallographic data for 1 and 2, respectively. These data can be
obtained free of charge from the Cambridge Crystallographic
Data Centre via www.ccdc.cam.ac.uk/datarequest.cif.
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