Construction of two interpenetrating coordination networks based on 4,4′-bis(1H-imidazol-1-yl-methyl)biphenyl and effect of carboxylic acids

Article abstract of DOI:10.1080/00958972.2014.895824

To investigate the construction of interpenetrating coordination networks and the effect of ligands, [Zn(bimb)(bdc)]·H₂O (1) and [Zn(bimb)(Hbtc)]·H₂O (2) [bimb = 4,4′-bis(1H-imidazol-1- yl-methyl)biphenyl; H₂bdc = 1,2-benzenedicarboxylic acid; H ₃btc = 1,3,5-benzenetricarboxylic acid] were hydrothermally synthesized and characterized by elemental analysis, IR spectra, Powder X-ray diffraction, and thermogravimetric analysis. Complex 1 shows a 3-D uoc type topology with twofold interpenetration. However, 2 exhibits a different 2-D self-penetrating network owing to hydrogen bonds of Hbtc between the two interpenetrating sql sheets, indicating that different carboxylic ligands could affect the interpenetration structures. Photoluminescence of bimb and the two complexes are also studied.

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Construction of two interpenetrating
coordination networks based on 4,4′-
bis(1H-imidazol-1-yl-methyl)biphenyl
and effect of carboxylic acids
Ying-Hui Yuab, Bo Wenb, Han-Zhong Zhangb, Guang-Feng Houa, Jin-
Sheng Gaoab & Peng-Fei Yanb
a Engineering Research Center of Pesticide of Heilongjiang
University, Heilongjiang University, Harbin, China
b School of Chemistry and Materials Science, Heilongjiang
University, Harbin, China
Accepted author version posted online: 26 Feb 2014.Published
Click for updates
online: 19 Mar 2014.
To cite this article: Ying-Hui Yu, Bo Wen, Han-Zhong Zhang, Guang-Feng Hou, Jin-Sheng Gao &
Peng-Fei Yan (2014) Construction of two interpenetrating coordination networks based on 4,4′-
bis(1H-imidazol-1-yl-methyl)biphenyl and effect of carboxylic acids, Journal of Coordination
Chemistry, 67:4, 588-596, DOI: 10.1080/00958972.2014.895824
To link to this article: http://dx.doi.org/10.1080/00958972.2014.895824
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Journal of Coordination Chemistry, 2014
Vol. 67, No. 4, 588–596, http://dx.doi.org/10.1080/00958972.2014.895824
Construction of two interpenetrating coordination networks
based on 4,4′-bis(1H-imidazol-1-yl-methyl)biphenyl and effect
of carboxylic acids
YING-HUI YU†‡, BO WEN‡, HAN-ZHONG ZHANG‡, GUANG-FENG HOU†,
JIN-SHENG GAO*†‡ and PENG-FEI YAN‡
†Engineering Research Center of Pesticide of Heilongjiang University, Heilongjiang University,
Harbin, China
‡School of Chemistry and Materials Science, Heilongjiang University, Harbin, China
(Received 30 August 2013; accepted 16 December 2013)
3D framework with 2-fold interpenetration
2D framework with self-penetration
[Zn(bimb)(bdc)]
(2)
H2O(1)
[Zn(bimb)(Hbtc)]
H3btc
H2O
H2bdc
bimb
Effect of H2bdc and H3btc as different mixed ligand on the structures of zinc coordination polymers
based on bimb
To investigate the construction of interpenetrating coordination networks and the effect of ligands,
[Zn(bimb)(bdc)]·H2O (1) and [Zn(bimb)(Hbtc)]·H2O (2) [bimb = 4,4′-bis(1H-imidazol-1-yl-methyl)
biphenyl; H2bdc = 1,2-benzenedicarboxylic acid; H3btc = 1,3,5-benzenetricarboxylic acid] were
hydrothermally synthesized and characterized by elemental analysis, IR spectra, Powder X-ray dif-
fraction, and thermogravimetric analysis. Complex 1 shows a 3-D uoc type topology with twofold
interpenetration. However, 2 exhibits a different 2-D self-penetrating network owing to hydrogen
bonds of Hbtc between the two interpenetrating sql sheets, indicating that different carboxylic
ligands could affect the interpenetration structures. Photoluminescence of bimb and the two com-
plexes are also studied.
Keywords: Crystal structure; Metal-organic frameworks; Interpenetration; Self-penetration;
Photoluminescence property
1. Introduction
The design and synthesis of metal-organic frameworks (MOFs) with interesting structures
and properties have been an area of rapid growth for potential applications as functional
*Corresponding author. Email: gaojins@hlju.edu.cn
© 2014 Taylor & Francis

Interpenetration frameworks
589
materials and interesting molecular topologies [1]. Many coordination networks are fasci-
nating for different entanglements. Interpenetrating networks are the most studied entangled
arrays, arising from large free voids in a single network. Batten and Robson restricted the
scope of interpenetrating structures wherein the building blocks within individual infinite
networks or chains are linked through either metal-to-ligand bonds or hydrogen bonds [2].
When the individual networks are sufficiently open, interpenetration can occur [3]. Self-
penetrating frameworks represent a subclass of interpenetration, featuring one of the “short-
est rings” being catenated by other “shortest rings” of the same net [4].
Although many interesting coordination networks have been reported, it is still a challenge
to predict the structure. The degree of interpenetration is strongly affected by the length of
the spacer ligand. There are, however, other factors that are related to interpenetration, such
as bulkiness of the ligands and the counterions, the number and type of solvated molecules,
π–π interactions between the aromatic bridging ligands, and coordination geometries [5].
Flexible N-donors such as 1,4-bis(imidazole-l-ylmethyl)benzene (bix) have been widely
adopted in the construction of MOFs with diverse topologies [6], many of which show dif-
ferent entanglement [7]. Compared with bix, 4,4′-bis(1H-imidazol-1-yl-methyl)biphenyl
(bimb) is a longer spacer ligand with more flexibility that can adopt different conformations,
based on which 1-, 2-, and 3-D structures were obtained [8]. Considering its long and flexi-
ble biphenyl group is favorable for formation of frameworks with large cavities, bimb is
adopted in our study for the construction of high-dimensional interpenetrating structures.
Herein, we investigate the influence of different carboxylic acids on the formation of
interpenetration structures based on bimb. We report two coordination complexes,
[Zn(bimb)(bdc)]·H2O (1) and [Zn(bimb)(Hbtc)]·H2O (2), based on 1,2-benzenedicarboxylic
acid (H2bdc) and 1,3,5-benzenetricarboxylic acid (H3btc), respectively. Complex 1 shows a
3-D network with twofold interpenetrating uoc net, hydrothermally synthesized by reacting
zinc nitrate with bimb and H2bdc. Complex 2 was obtained following the same procedure as
for 1 except that H3btc was used instead of H2bdc. However, 2 exhibits a different 2-D self-
penetration network. The structures of bimb, H2bdc, and H3btc are shown in scheme 1. The
thermal stabilities and photoluminescence of the two complexes have also been described.
N
N
bimb
N
N
COOH
H2bdc
COOH
COOH
H3btc
COOH
COOH
Scheme 1. Structures of bimb, H2bdc and H3btc.

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Y.-H. Yu et al.
2. Experimental setup
2.1. Materials and measurements
Zinc nitrate, ethanol, imidazole, and 1,2-benzenedicarboxylic acid are from Kermel and
4,4′-bis(chloromethyl)-1,1′-biphenyl from J&K Chemicals. All chemicals purchased are of
reagent grade and used as received.
Elemental analyses for C, H, and N were carried out on a Vario EL III elemental ana-
lyzer. IR spectrum was recorded on a Bruker tensor 27 FT-IR spectrophotometer from 4000
to 400 cm−1 using KBr pellets. Photoluminescence spectra were taken on a Perkin Elmer
Corporation Model Fluorescence Spectrometer LS 55 PL. Photoluminescence spectra were
performed on solid samples after the crystals were crushed and put between quartz plates.
Thermogravimetric analyses were carried out with a Perkin Elmer DTA-1700 with a heating
rate of 10 °C min−1 from 25 to 800 °C. Powder X-ray diffraction (PXRD) measurement,
from 2θ 5° to 50°, was performed on a Rigaku D/Max−IIIB with X-ray diffractometer Cu
Kα (λ = 1.5406 Å) radiation (40 kV and 200 mA) and Ni filter.
2.2. Synthesis
2.2.1. Synthesis of [Zn(bimb)(bdc)]·H2O (1). 4,4′-Bis(1H-imidazol-1-yl-methyl)biphenyl
(bimb) was prepared following the literature procedure [9]. Zn(NO3)2·6H2O (0.12 g, 0.40
mM), bimb (0.13 g, 0.40 mM), H2bdc (0.07 g, 0.40 mM), H2O (4 mL), and ethanol (4 mL)
were stirred for 10 min in air, then the pH was adjusted to 6–7 by 1 M NaOH solution
before the mixture was transferred and sealed in a 20 mL teflon-lined stainless autoclave,
which was heated at 140 °C for 3 days and then cooled to room temperature. About 0.119 g
colorless block crystals were filtered and washed with distilled water and ethanol (53%
yield based on ZnII cation). Elemental analysis: Calcd for C28H24N4O5Zn (561.88): C,
59.85%; H, 4.31%; N, 9.97%. Found: C, 59.92%; H, 4.39%; N, 10.01%. IR (KBr, cm−1):
3545 (w), 3447 (w), 3123 (w), 1695 (w), 1581 (m), 1498 (m), 1448 (m), 1398 (m), 1338
(w), 1280 (m), 1230 (m), 1187 (w), 1099 (s), 1005 (w), 952 (m), 827 (s), 750(s), 691 (w),
627 (w), 502 (w).
2.2.2. Synthesis of [Zn(bimb)(Hbtc)]·H2O (2). The preparation of 2 was similar to that
of 1 except that H3tbc (0.08 g, 0.40 mM) instead of H2bdc was used. About 0.114 g color-
less block crystals were obtained after filtration and washed with distilled water and ethanol
(47% yield based on ZnII). Elemental analysis: Calcd for C29H24N4O7Zn (605.91): C,
57.49%; H, 3.99%; N, 9.25%. Found: C, 57.31%; H, 3.72%; N, 9.39%. IR (KBr, cm−1):
3133 (w), 1715 (s), 1617 (s), 1577 (m), 1357 (s), 1230 (m), 1166 (m), 1093 (m), 951 (w),
830 (w), 798 (w), 779 (s), 654 (m).
2.3. X-ray crystallography
Single-crystal X-ray diffraction data for 1 and 2 were collected on a Rigaku R-AXIS
RAPID imaging plate diffractometer with graphite-monochromated Mo-Kα radiation (λ =
0.71073 Å) at 291 K. Empirical absorption corrections based on equivalent reflections were
applied. The structures of 1 and 2 were solved by direct methods and refined by full-matrix
least-squares method on F2 using the SHELXS-97 crystallographic software package [10].

Interpenetration frameworks
591
Table 1. Crystal data and structure refinements for 1 and 2.
1
2
Empirical formula
Fw
C28H24N4O5Zn
561.88
C29H24N4O7Zn
605.91
Crystal system
Space group
a (Å)
b (Å)
c (Å)
Tetragonal
I41/a
19.891(3)
19.891(2)
26.227(5)
90
Monoclinic
P21/c
11.138(2)
19.068(4)
16.848(5)
90
α (°)
β (°)
90
90
10,377(3)
16
1.439
130.143(19)
90
2735.3(11)
4
1.471
0.953
γ (°)
V (Å3)
Z
DCalcd (mg m−3
)
μ (mm−1
F (0 0 0)
)
0.993
4640
1248
Collected/unique
R(int)
48,423/5924
0.0887
1.035
0.0436; 0.0919
0.0837; 0.1051
24,938/6134
0.0497
1.027
0.0588; 0.1676
0.0849; 0.1898
GOF on F2
Rla [I > 2σ(I)]; wR2 [I > σ(I)]
b
b
Rla (all); wR2 (all)
aR1 = Σ||Fo| − |Fc||/Σ|Fo|.
bwR2 = {Σ[w(Fo2− Fc2)2/Σw(Fo2)2]}1/2
.
Table 2. Selected bond lengths [Å] and angles [°] of 1 and 2.
Complex 1
Zn(1)–O(4)
Zn(1)–N(1)
O(4)–Zn(1)–N(1)
O(4)–Zn(1)–O(1)
N(1)–Zn(1)–O(1)
1.9954(19)
1.996(2)
105.11(9)
107.11(8)
108.51(9)
Zn(1)–N(3)
Zn(1)–O(1)
O(4)–Zn(1)–N(3)
N(1)–Zn(1)–N(3)
O(1)–Zn(1)–N(3)
2.006(2)
1.9970(19)
104.20(9)
125.05(10)
105.71(9)
Complex 2
N(1)–Zn(1)
2.021(4)
O(1)–Zn(1)
1.920(3)
N(3)–Zn(1)
2.022(3)
O(5)–Zn(1)
1.930(3)
O(1)–Zn(1)–O(5)
O(5)–Zn(1)–N(1)
O(5)–Zn(1)–N(3)
118.62(14)
102.27(13)
112.41(13)
O(1)–Zn(1)–N(1)
O(1)–Zn(1)–N(3)
N(1)–Zn(1)–N(3)
115.05(13)
105.40(13)
102.06(14)
All non-hydrogen atoms were refined anisotropically. Hydrogens of bimb and bdc were
placed in calculated positions and treated as riding on their parent. In 1, hydrogens of water
were located in the difference Fourier map and refined as riding on their parent oxygen.
However, in 2, hydrogens of water were not added. The crystal parameters, data collection,
and refinement results for 1 and 2 are summarized in table 1. Selected bond lengths and
angles are listed in table 2. Crystallography data have been deposited to the Cambridge
Crystallography Data Center with deposition numbers CCDC: 953109 and 953110.
3. Results and discussion
3.1. Structure description
Single-crystal X-ray diffraction analysis shows that the asymmetric unit of 1 contains two
half bimb molecules, one ZnII, one bdc anion, and one lattice water [figure 1(a)]. ZnII is

592
Y.-H. Yu et al.
Figure 1. (a) Stick–ball representation of the structure of 1 with thermal ellipsoids at 50% probability, where
hydrogens are omitted for clarity; (b) schematic illustration of 3-D four-connected uoc type topology with a point
symbol of (42·84); (c) twofold interpenetrated uoc net. Symmetry codes: (I) –x, 0.5 – y, z; (II) –x, 1.5 – y, z; (III)
–0.25 + y, 0.75 – x, –0.25 + z.
four-coordinate in a tetrahedral environment defined by two N from two bimb molecules
and two O from two bdc anions. As shown in figure 1(a), two helical chains with a same
inner diameter of 6.369(1) Å along [1 0 0] and [0 1 0] directions, respectively, were formed
by two bimb molecules with cis-conformation bridging the ZnII cations. Another helical
chain with a relatively small inner diameter of 2.662(1) Å along the [0 0 1] direction is built
up by bdc anions linking ZnII cations. The three helical chains with different rotation direc-
tions connect to construct an unusual 3-D uoc [11] type topology with Class IIa interpene-
tration and a point symbol (42·84) [figure 1(b)]. A large cavity of 12.572(2) Å × 13.643(3) Å
along the [0 1 0] direction in 1 causes the occurrence of a twofold interpenetrating unusual
uoc network with the uncoordinated water filling into the interspaces [figure 1(c)]. Such
coordination networks with uoc twofold structures have been observed and reported very
rarely. Hong [12] and Dietzel [13] reported a uoc twofold structure constructed by diphenic
acid and 4,4′-bipyridine as mixed ligands coordinating with zinc. Similar to 1, ZnII in the

Interpenetration frameworks
593
Figure 2. (a) Stick–ball representation of the structure of 2, where hydrogens are omitted for clarity; (b) schematic
illustration of 2-D sq1 net; (c) 2-D 4,4L42 self-penetrating network with point symbol of (54·6·8)(55·6) when Hbtc
is regarded as a four-connecting node. Symmetry codes: (I) 2 + x, y, 1 + z; (II) 3 – x, −0.5 + y, 1.5 – z.
reported complex are also four-coordinate in a tetrahedral environment defined by two N
from 4,4′-bipyridine and two O from diphenic acid. Both 1 and the reported complex are
obtained from two ligands, one of which is nitrogen containing heterocyclic and the other is
polycarboxylic acid, with twofold interpenetrating 3-D networks.
Complex 2 crystallizes in a monoclinic system with an asymmetric unit consisting of one
bimb, one ZnII, one Hbtc, and one lattice water [figure 2(a)]. The ZnII is four-coordinate by
two N from two bimb and two O from two Hbtc anions; the Zn–N and Zn–O distances are
1.997–2.015(2) Å. As shown in figure 2(a), bimb molecules take trans-conformation and
connect ZnII cations to form a zigzag chain along the [1 0 0] direction. Hbtc anions link
adjacent chains constructing a 2-D sq1 net with a large cavity of 10.259(2) Å × 17.209(3)
Å, resulting in interpenetration similar to that in 1. Interpenetrating sq1 sheets are connected
by hydrogen bonds O3–H3A⋯O2 (2.634(4) Å) of Hbtc anions to give a 2-D 4,4L42 type
self-penetration network with a point symbol of (54·6·8)(55·6) when Hbtc is a four-connect-
ing node. As described in a review [14], self-penetration is single network in which the
smallest topological circuits are penetrated by themselves. As a kind of special interpenetra-
tion, it occured uncommonly compared with the other interpenetration structures.
Our previous investigation indicated that bimb with a long spacer could induce the for-
mation of interpenetration structures, which could be tuned by the presence of H2bdc as an
additional ligand [15]. The aim of this study is to understand the effect of H2bdc and H3btc
on the construction of interpenetrating frameworks. We got one 3-D network with twofold

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Y.-H. Yu et al.
interpenetrating structure based on H2bdc and one 2-D self-penetrating network formed by
two interpenetrating sheets connected through hydrogen bonds based on H3btc under the
same reaction conditions. In 2, only two carboxylic groups of H3btc coordinated with ZnII
because one hydrogen of carboxylic group was not deprotonated, forming hydrogen bonds
to bridge two interpenetrating sheets into a self-penetration network. The structural differ-
ences between 1 and 2 could be attributed to the incomplete deprotonation of H3btc, which
provides the hydrogen bonds for two interpenetrating sheets connecting together.
3.2. Powder X-ray diffraction and thermogravimetric analysis
PXRD and thermogravimetric analysis (TGA) were carried out to investigate phase purities
and stabilities of 1 and 2. PXRD patterns for 1 and 2 were performed at room temperature
(figure S2, ESI†). The locations and intensities of diffraction peaks of experimental patterns
match well with the calculated ones, indicating that these two coordination polymers were
synthesized as a single phase. TG measurements of 1 and 2 were carried out from 20 to
800 °C (figure S3, ESI†). Complex 1 shows that the first weight loss of 3.42% at
50–243 °C corresponds to loss of two lattice waters (Calcd 3.21%). The network starts to
collapse at 262 °C and the second weight loss of 84.67% (Calcd 85.52%) from 262 to
502 °C can be ascribed to the removal of all bimb and bdc ligands, resulting in ZnO. For 2,
the first weight loss of 3.91% at 50–190 °C was consistent with loss of one lattice water
(Calcd 2.97%). The network of 2 collapses at 327 °C, then loses 84.92% of its weight
between 327 and 550 °C, corresponding to the decomposition of bimb and btc (Calcd
86.57%) with the resulting residue of ZnO. The results of PXRD and TGA are consistent
with the structures of the two complexes.
3.3. Photoluminescence properties
The photoluminescent properties of coordination polymers, especially those with d10 metal
centers, have been widely investigated [16], owing to their higher thermal stability than
Figure 3. Solid-state photoluminescence spectra of bimb, 1 and 2.

Interpenetration frameworks
595
pure organic materials and the ability to tune the emission wavelength by metal coordina-
tion. Zinc(II) is frequently adopted for potential fluorescence-emitting coordination poly-
mers [17]. We studied the photoluminescence properties of bimb, 1 and 2 in the solid state
at room temperature. As shown in figure 3, bimb exhibits two emission bands at 428 and
464 nm (λex = 350 nm). In 1 and 2, since absorption spectra are similar to that of bimb, the
absorption bands can be assigned to π*→π intraligand fluorescence. Emission intensities of
1 and 2 exhibit an increase in contrast to bimb, presumably owing to the bending of ligand
bonds caused by coordination.
4. Conclusion
Two coordination networks were constructed by hydrothermal reactions of zinc nitrate,
bimb with H2bdc or H3btc. Present investigations demonstrate that a long and flexible
ligand bimb tends to form structures with large cavities, favorable for the occurrence of
interpenetration. Complex 1 shows a 3-D framework with twofold uoc interpenetration; 2
exhibits a different 2-D self-penetration network, due to hydrogen bonds of Hbtc connecting
two interpenetrating sq1 sheets. The presence of hydrogen bonds is an inducement for such
a self-penetrating formation. Photoluminescence of bimb, 1, and 2 show that the absorptions
can be assigned to π*→π intraligand fluorescence with increase of the emission intensities
upon coordination.
Supplementary material
IR spectra(figure S1), PXRD patterns (figures S2) and TGA curves(figures S3) of the
related compounds. Supplementary data associated with this article can be found in the
online version at http://dx.doi.org/10.1080/00958972.2014.895824.
Funding
The work is financially supported by the Natural Science Foundation of Heilongjiang Province [grant
number B201108]; Science and Technology Planning Project of Heilongjiang Province [grant number
WJ09B03]; Scientific Research Fund of Heilongjiang Provincial Education Department [grant number
12531512].
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