Molecular tectonics: Generation of 2-D molecular networks by combination of coordination and hydrogen bonds

Article abstract of DOI:10.1039/b512569n

The combination of two organic tectons 1 and 2, based on a 1,4-phenylenediamine backbone functionalised with two pyridine units through amide junctions with HgCl₂, leads to the formation of two types of 2-D networks, one of the purely metallo-o

Full text of DOI:10.1039/b512569n

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www.rsc.org/njc | New Journal of Chemistry
Molecular tectonics: generation of 2-D molecular networks by
combination of coordination and hydrogen bonds
ˆ
´
Jerome Pansanel, Abdelaziz Jouaiti, Sylvie Ferlay, Mir Wais Hosseini,*
Jean-Marc Planeix and Nathalie Kyritsakas
Received (in Durham, UK) 5th September 2005, Accepted 3rd November 2005
First published as an Advance Article on the web 15th November 2005
DOI: 10.1039/b512569n
The combination of two organic tectons 1 and 2, based on a 1,4-phenylenediamine backbone
functionalised with two pyridine units through amide junctions with HgCl2, leads to the
formation of two types of 2-D networks, one of the purely metallo-organic type, based on only
coordination bonds, and the other combining both coordination and hydrogen bonds.
ourselves on one hand to a combination of hydrogen and
Introduction
coordination bonds and on the other hand to the formation
of 1- and 2-D networks (Fig. 1).
Molecular tectonics1–3 is a branch of chemistry dealing with
the design, formation and description of molecular networks.4
This approach is based on individual molecular building
blocks or tectons2 bearing in their structure complementary
interaction sites defining recognition patterns. By repetitive
processes, these tectons generate molecular networks by trans-
lation of recognition patterns. In the crystalline phase, mole-
cular networks are infinite periodic architectures formed upon
mutual interconnection between complementary or self-com-
plementary building tectons. Thus, molecular networks are
defined by the nature of tectons composing the architecture
(shape, interaction sites, and their localisation in space), the
type of interaction involved in the interconnection of conse-
cutive tectons and finally, the number of independent transla-
tions operating on the recognition patterns.4 The latter aspect
defines the dimensionality of the network (1-, 2- or 3-D). With
that respect, the definition of recognition patterns also called
supramolecular synthons5 which upon translation become
structural nodes of the network is an important issue. The
nature of the recognition pattern is related to the type of
interaction taking place between complementary or self-com-
plementary tectons. Various types of attractive interactions
(van der Waals contacts, hydrogen bond, coordination bond,
p–p, p–cation and electrostatic interactions) have been used to
generate a huge variety of molecular networks. Among them,
three categories of networks, namely H-bonded,6 coordina-
tion7 and inclusion8 networks, are the most commonly re-
ported. However, it is of interest to notice that the formation
of the crystal imposes tridimensional packing of networks,
which also requires a variety of interactions. In other words,
when taking into account all possible interactions, a crystal by
definition is a 3-D network. Thus defining a network in the
crystalline phase is a subjective issue and requires a hierarch-
ical scale allowing the ranking of recognition patterns. The
most appropriate scale would be based on the energy of
interactions. For the sake of demonstration, let us restrict
In the case of a bidentate tecton bearing one H-bond and
one coordination bond generator (Fig. 1a), clearly two differ-
ent interaction patterns will take place and, since both patterns
are only translated in one direction of space, such a tecton will
lead to a 1-D network (Fig. 1d). If considering the pattern
based on the H-bond formation (Fig. 1b) as dominant, the
network would be qualified as H-bonded network. However, if
the coordination bond interconnecting consecutive tectons
(Fig. 1c) was considered as dominant, the network would be
described as a coordination network. The case of the tetra-
dentate tecton (Fig. 1e) is even more demonstrative. Indeed,
the 2-D network formed (Fig. 1h) may either be described as
resulting from the interconnection of consecutive 1-D
H-bonded networks (Fig. 1f) through coordination bonds
(Fig. 1g) or as resulting from the bridging of 1-D coordination
networks by H-bonding. However, based on the difference in
the energy of interactions, since a coordination bond is
stronger than an H-bond, one may consider the recognition
pattern based on the coordination bond as primary and the
other based on H-bond as secondary. Consequently both
networks would be qualified as metallo-organic coordination
networks.
Examples of simultaneous use of coordination bonds asso-
ciated with hydrogen bonds of the amide type have been
reported.9–11
Let us illustrate the above discussion by two real cases in
which the two isomeric tectons 1 and 2 (Scheme 1) are
combined with HgCl2. Both combinations lead to the forma-
tion of two different types of 2-D networks.
Results and discussion
The design of the organic tectons 1 and 2 (for preparation see
experimental section) is based on the aryl group bearing two
pyridine moieties as coordinating sites. The junction between
the two parts is effected by an amide group. The two tectons,
differing only by the position of connection of the amide group
to the pyridyl group (position 4 for 1 and 3 for 2), are
structural isomers. It worth noting that the amide junction
Laboratoire de Chimie de Coordination Organique, UMR CNRS
´
7140, Universite Louis Pasteur, F-67000 Strasbourg, France.
E-mail: hosseini@chimie.u-strasbg.fr
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Scheme 1
Structural isomers of 1 and 2 based on 1,2-phenylenedi-
amine and 1,3-phenylenediamine have been reported and were
shown to generate networks in the presence of a variety of
metal centres.11,12 The formation of a 1-D network based on
the use of the tecton 2 and HgI2 was also previously re-
ported.13
Since both tectons 1 and 2 are neutral units, in order to
avoid the presence of unbound anions, HgCl2 was chosen as a
neutral metallatecton. Furthermore, Hg(II) appeared to us as
an interesting cation since it presents rather loose coordination
demands. Indeed, it offers a variety of coordination numbers
(between 2 and 6) and geometries (linear, tetrahedral, octa-
hedral). Mercury halides have been previously used as metal-
latectons by others11–14 and by us.15
At room temperature, upon slow diffusion of an EtOH
solution of HgCl2 into a DMSO solution of 1, colourless
crystals were obtained after ca. one week. X-Ray diffraction
on a single crystal (Table 1) revealed that the crystal (mono-
clinic, P2/c) is exclusively composed of 1 and HgCl2. For the
organic moiety, presenting a centre of symmetry, among
various possible conformations and configurations (Fig. 2),
both amide groups (dCQO ¼ 1.23 A, dN–CO ¼ 1.35 A, dC–CO
¼
1.49 A) of the tecton 1 adopt the trans configuration (HNCO
dihedral angles of ꢂ172.41 and þ172.51). The amide groups
are neither coplanar with the aryl ring nor the pyridine unit
but tilted by 37.51 and 31.01, respectively. Interestingly, the
oxygen atom of the CQO group is located at 2.55 and 2.70 A
from the nearest hydrogen atoms of the aryl group and
pyridine, respectively.
When considering only the formation of coordination
bonds, the crystal may be described as a neutral 1-D network
resulting from the bridging of organic tectons 1 by HgCl2
units. The interconnection takes place through the coordina-
tion of Hg(II) by the nitrogen atoms of the pyridine group
belonging to consecutive tectons 1 (Fig. 3). The mercury cation
is surrounded by two Cl anions (dHg–Cl ¼ 2.35 A) and two N
atoms (dHg–N ¼ 2.44 A) belonging to two consecutive tectons
1. The metal centre adopts a distorted tetrahedral coordina-
tion geometry (NHgN angle of 96.51, ClHgCl angle of 152.51
and NHgCl angle of 95.0 and 103.21).
However, the analysis of the packing of 1-D networks in a
plane allowed us to spot another type of specific interaction
between consecutive 1-D networks. Indeed, due to the trans
configuration of both amide groups (anti–anti, see Fig. 2) and
antiparallel orientation of the CQO groups (see Fig. 2),
consecutive 1-D networks are interconnected through H bonds
Fig. 1 Schematic representation of 1- and 2-D networks based on
tectons bearing different interaction sites. Bidentate (a) or tetradentate
(e) tectons bearing X and Y sites able to establish H-bonds (b and f)
and coordination bonds (c and g) lead, upon combination of both
modes of interactions, to the formation of 1-D (d) or 2-D (h) networks.
might not be an innocent connecting group since it may either
be involved in the binding of the metal centre through the
oxygen atom of its CQO moiety or establish a hydrogen bond
of NHꢁ ꢁ ꢁO type. Although all three components (aryl moiety,
pyridine and HNCO group) of both tectons 1 and 2 are rigid
units, both possess rotational flexibility and may adopt a
variety of conformations and configurations due to the rota-
tional barrier of the amide group (Fig. 2).
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Fig. 3 Portions of the structure of the 2-D coordination networks
formed between 1 and HgCl2. The 2-D network is generated by both
coordination (Hg–Npy) and H bonds (NHꢁ ꢁ ꢁOQC). The arrows
represent the gradual construction of the network. For the sake of
clarity, H atoms, except those involved in H-bonding, are not repre-
sented. For bond distances and angles see text.
ing to the consecutive strand (Fig. 4). Both aryl and pyridine
rings belonging to consecutive 1-D networks are parallel,
however the distance of ca. 5.0 A clearly shows the absence
of direct interactions. When taking into account all specific
interactions, the structure may be described as a 2-D network
based on two types of recognition pattern, one of the coordi-
nation type and the other of H-bonding type. As discussed in
the introduction of this contribution (Fig. 1), when taking into
account energetic factors, the coordination pattern may be
considered as primary and the H-bond pattern as secondary.
The network may then be considered as a coordination net-
work. The same type of arrangement has been previously
observed for the combination of the ortho isomer of 2 based
on 1,2-phenylenediamine with HgCl2.11
Fig. 2 Representation of some of the different conformations and
configurations which may be adopted by tectons 1 and 2 supposing
that the aryl ring, the pyridine and the amide group are in the same
plane.
(dNHꢁ ꢁ ꢁO ¼ 2.04 A, NHO angle of 163.01) between the CQO
groups belonging to one strand and the NH moieties belong-
Table 1 Data collection and refinements for 1 ꢁ HgCl2 and 2 ꢁ HgCl2
1 ꢁ HgCl2
2 ꢁ HgCl2
Formula
Molecular weight
C18H14N4O2 ꢁ HgCl2 C18H14N4O2 ꢁ HgCl2
589.84 589.84
[g molꢂ1
]
Crystal system
Space group
a [A]
b [A]
c [A]
Monoclinic
P2/c
Monoclinic
P21/n
At room temperature, upon slow diffusion of an EtOH
solution of HgCl2 into a DMSO solution of 2, colourless
13.0454(5)
5.0255(10)
13.777(2)
96.005(9)
898.2(2)
2
8.3336(2)
9.2373(2)
11.4459(3)
94.207(5)
878.73(4)
2
b [1]
V [A3]
Z
Colour
Colorless
Colorless
Crystal size [mm]
rcalcd [g cmꢂ3
F(000)
0.26 ꢃ 0.10 ꢃ 0.05 0.10 ꢃ 0.10 ꢃ 0.08
]
2.181 2.23
560
8.888
173
560
9.085
173
m [mmꢂ1
Temperature [K]
]
l [A]
Radiation
Diffractometer
Scan mode
0.71073
MoKa
KappaCCD
Phi scans
0.71073
MoKa
KappaCCD
CCD
j range for collection [1] 2.97/32.99
2.5/30.03
4717
1928
Number of reflections
Number of data with
3354
2557
Fig. 4 Schematic representation of the 2-D network formed upon
combining both coordination and H-bonds. The 2-D network may be
regarded as 1-D coordination networks, obtained upon mutual brid-
ging between metal centres and organic tectons 1, interconnected
through H-bonds taking place between amide groups.
I 4 3 s(I)
Number of variables
R
wR
GOF
123
124
0.0328
0.0912
1.081
0.017
0.022
0.976
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Fig. 5 Portions of the structure of the 2-D coordination networks
formed between 2 and HgCl2. The 2-D network is exclusively gener-
ated through coordination bonds (Hg–Npy and Hg–OQC) between 2
and the mercury cation adopting the octahedral coordination geome-
try. The arrows represent the gradual construction of the network. For
the sake of clarity, H atoms are not represented. For bond distances
and angles see text.
crystals were again obtained after ca. one week and analysed
by X-ray diffraction on a single crystal (Table 1). The crystal
(monoclinic, P21/n) was again exclusively composed of 2 and
HgCl2. Again, the tecton 2 possesses a centre of symmetry and
adopts the anti configuration (antiparallel orientation of the
CQO groups) as in the case of 1 mentioned above. Both amide
groups (dCQO ¼ 1.22 A, dN–CO ¼ 1.36 A, dC–CO ¼ 1.50 A) of
the tecton 2 adopt the trans configuration (HNCO dihedral
angles of ꢂ166.51 and þ166.41). The amide groups are again
neither coplanar with the aryl ring nor with the pyridine unit
but tilted by 36.01 and 33.21, respectively. As in the case of 1,
the oxygen atom of the CQO group is located at 2.35 and 2.54
A from the nearest hydrogen atoms of the aryl group and
pyridine, respectively.
Fig. 6 Schematic representation of a systematic analysis of the
possible modes of connection between the tecton 2, adopting syn
and anti arrangements of the CO groups, and the mercury cation
adopting the octahedral coordination geometry. Only the arrangement
depicted in d (bottom) leads to the absence of coordination frustration
(for the description of the four cases represented see text).
geometry, in the case of 2, the donor centres are arranged in
the rather less common octahedral geometry (NHgN, OHgO
and ClHgCl angles of 180.01, OHgCl angles of 92.91 and 87.01
and NHgCl angles of 91.2 and 88.81). The 2-D network may
be described as 1-D coordination networks, formed upon
bridging of consecutive tectons 2 by HgCl2 complexes through
coordination bonds established between pyridine type nitro-
gen atoms and Hg(II) centres. The resulting 1-D networks are
further connected through coordination bonds between the
carbonyl groups of 2 and mercury centres (Fig. 5).
The interconnection between the tecton 2 and HgCl2 leads
to the formation of a neutral 2-D network. The coordination
sphere around Hg(II) is composed of two chloride anions
(dHg–Cl ¼ 2.38 A), two nitrogen (dHg–N ¼ 2.62 A) and two
oxygen (dHg–O ¼ 2.70 A) atoms. In marked contrast with the
above mentioned case in which, in the presence of the tecton 1,
Hg(II) adopts the rather common tetrahedral coordination
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In order to better understand the formation of the 2-D
network, we analysed, in a systematic way, different possibi-
lities based on the combination of two conformations (syn
parallel and antiparallel) of the tecton 2 with a metal centre
adopting the octahedral coordination geometry. In order to
simplify the analysis, we supposed that both amide junctions
adopt the trans configuration as observed both in the case of 1
and 2 and that only the nitrogen atom of the pyridine ring and
oxygen atom of the carbonyl moiety take part in the coordina-
tion (Fig. 6). It is worth noting that when the tecton 2 is
combined with HgI2, only a 1-D network is observed.13
Indeed, the coordination between 2 and Hg(II) takes place
only with the nitrogen atoms of the pyridine units and the CQO
groups do not participate in the binding of metal centres.
In the case of 2 adopting the syn parallel conformation (Fig.
2) for which the two CQO groups are oriented towards the
same face of the tecton (Fig. 6 a, b and c), all arrangements
lead to frustration in the coordination pattern. Indeed, in all
three cases, all CQO groups cannot be coordinated to metal
centres. Interestingly, only in the case of the antiparallel
conformation, no frustration is obtained (Fig. 6d). This is
indeed what is observed in the case of 2 which adopts indeed
the antiparallel arrangement.
(s, 2H, NH); 13C (75.48 MHz, CDCl3, 25 1C), d (ppm): 121.2;
124.0; 131.0; 135.2; 135.9; 149.0; 152.5; 164.4. Anal. for
C18H14N4O2 (318.34 g molꢂ1), calcd: C: 67.9%, H: 4.4%, N:
17.6%; found: C: 65.8%, H: 4.3%, N: 16.8%.
Compound 2. 1H NMR (300 MHz, CDCl3, 25 1C): d (ppm):
7.78 (s, 4H, H-Ar); 7.88 (d, J ¼ 6 Hz, 4H, H-Py); 8.79 (d, J ¼ 6
Hz, 4H, H-Py); 10.52 (s, 2H, NH); 13C (75.48 MHz, CDCl3,
25 1C), d (ppm): 121.2; 122.0; 135.2; 142.3; 150.7; 164.4. Anal.
for C18H14N4O2 (318.34 g molꢂ1), calcd: C: 67.9%, H: 4.4%,
N: 17.6%; found: C: 67.3%, H: 4.4%, N: 17.5%.
Crystallisation conditions
In a crystallisation tube (height ¼ 15 cm, diameter ¼ 0.4 cm),
at room temperature upon slow diffusion of an EtOH solution
(1 ml) of HgCl2 (6 ꢃ 10ꢂ6 moles) into a DMSO solution (1 ml)
of 1 or 2 (6 ꢃ 10ꢂ6 moles), colourless crystals were obtained
after ca. one week.
Crystallography
Data were collected at 173(2) K on a Bruker SMART CCD
Diffractometer equipped with an Oxford Cryosystem liquid
N2 device, using graphite-monochromated Mo-Ka (l ¼
0.71073) radiation. For all structures, diffraction data were
corrected for absorption and structural determination was
achieved using the APEX (1.022) package. All hydrogen
atoms have been calculated except those connected to disor-
dered atoms. CCDC reference numbers 284053–284054. For
crystallographic data in CIF or other electronic format see
DOI: 10.1039/b512569n
Conclusion
Upon combining two structural isomeric organic tectons 1 and
2, based on the aryl group bearing two pyridine units con-
nected through amide junctions, with HgCl2 acting as a
metallatecton, two different bidimensional networks have been
generated. Whereas for the tecton 2 the combination leads to a
2-D network exclusively based on two types of coordination
bonds (Hg–Npy and Hg–OQC), in the case of 1, the network
is generated through both coordination bonding (Hg–Npy)
and H-bonding (NHꢁ ꢁ ꢁOQC) taking place between amide
groups. With the aim of increasing the dimensionality of
molecular networks, we are currently exploring other possibi-
lities of combining different types of interactions.
Acknowledgements
Universite Louis Pasteur, Institut Universitaire de France, the
´
CNRS and the Ministry of Education and Research are
acknowledged for financial support and for a scholarship
to J. P.
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76 | New J. Chem., 2006, 30, 71–76