Synthesis, structure, and electrochemistry and magnetic properties of a novel 1D homochiral MnIII(5-Brsalen) coordination polymer with left-handed helical character

Article abstract of DOI:10.1016/j.molstruc.2015.09.031

A novel homochiral manganese (III) Mn(5-Brsalen) coordination polymer with left-handed helical character by spontaneous resolution on crystallization by using Mn(5-Brsalen) and 4,4-bipyridine, [Mn^III(5-Brsalen)(4,4-bipy)]·ClO₄·CH

Full text of DOI:10.1016/j.molstruc.2015.09.031

Journal of Molecular Structure 1104 (2016) 58e62
Contents lists available at ScienceDirect
Journal of Molecular Structure
journal homepage: http://www.elsevier.com/locate/molstruc
Synthesis, structure, and electrochemistry and magnetic properties of
a novel 1D homochiral MnIII(5-Brsalen) coordination polymer with
left-handed helical character
Dapeng Dong, Naisen Yu, Haiyan Zhao, Dedi Liu, Jia Liu, Zhenghua Li, Dongping Liu*
Liaoning Key Laboratory of Optoelectronic Films and Materials, School of Physics and Materials Engineering, Dalian Nationalities University, Dalian,
PR China
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 3 July 2015
Received in revised form
9 September 2015
Accepted 29 September 2015
Available online 3 October 2015
A novel homochiral manganese (III) Mn(5-Brsalen) coordination polymer with left-handed helical
character by spontaneous resolution on crystallization by using Mn(5-Brsalen) and 4,4-bipyridine,
[MnIII(5-Brsalen)(4,4-bipy)]$ClO4$CH3OH (1) (4,4-bipy ¼ 4,4-bipyridine) has been synthesized and
structurally characterized by X-ray single-crystal diffraction, elemental analysis and infrared spectros-
copy. In compound 1, each manganese(III) anion is six-coordinate octahedral being bonded to four atoms
of 5-Brsalen ligand in an equatorial plane and two nitrogen atoms from a 4,4-bipyridine ligand in axial
positions. The structure of compound 1 can be described a supramolecular 2D-like structure which was
Keywords:
Spontaneous resolution
Chirality
Crystal structure
Electrochemistry
formed by the intermolecular
p-stacking interactions between the neighboring chains of the aromatic
rings of 4,4-bipyridine and 5-Brsalen molecules. UVevis absorption spectrum, electrochemistry and
magnetic properties of the compound 1 have also been studied.
© 2015 Elsevier B.V. All rights reserved.
1. Introduction
solution [13e19]. Moreover, spontaneous resolution is relatively
rare and cannot be predicted because its mechanism is not yet fully
Chirality is an essential element for life, which plays a key role in
biological system and pharmacy, as well as in advanced materials
such as asymmetric catalysis, chiral separation and nonlinear op-
tical devices [1e5]. The general approach to a chiral framework is
using a chiral molecule as the primary linker or as an inducer of
final chirality, which is the most effective method for the synthesis
of chiral coordination polymers [6e9]. However, due to the limi-
tation of the chiral pool and very often the high cost of chiral li-
gands, it is highly desirable to create chiral compounds from achiral
precursors. Spontaneous resolution on crystallization without any
chiral auxiliary usually yields chiral conglomerate, which has been
proved as a constructive approach for the synthesis of individual
chiral metaleorganic coordination polymers [10e12]. However, the
controllable generation of such chiral frameworks from totally
achiral precursors is still of a great challenge since it may be
significantly governed by several factors such as the flexibility of
organic ligand, coordination geometry of the metal center, coun-
teranion, solvent, reaction temperature, and pH value of the
understood.
On the other hand, tetradentate H2salen and salen derivatives
are versatile ligands, which consisting of two nitrogen and two
oxygen donors to form stable metal complexes, are very popular O-
and N-donor linkers because of their excellent chelating capabil-
ities. Salen-type N2O2 ligands coordinate to various kinds of
transition-metal ions in a tetradentate fashion to produce stable
complexes which have found versatile applications in a wide range
of areas such as catalysis, biochemistry, electrochemistry, magnetic
properties, and luminescent materials [20e26]. Among them, some
manganese (III) complexes of salen type Schiff base ligands have
been synthesized in the past decades [27e29]. However, to the best
of our knowledge, the homochiral manganese (III) Mn(5-Brsalen)
coordination polymer with left-handed helical character by spon-
taneous resolution on crystallization have not been reported so far.
In this paper, we chose an achiral 5-BrsalenMn molecule as the
building unit and successfully synthesized a homochiral Mn(5-
Brsalen) coordination polymer with left-handed helical character,
[MnIII(5-Brsalen)(4,4-bipy)]$ClO4$CH3OH (1). The crystal structure,
electrochemistry and magnetic properties of compound 1 have also
been studied.
* Corresponding author.
E-mail address: dongping.liu@dlnu.edu.cn (D. Liu).
http://dx.doi.org/10.1016/j.molstruc.2015.09.031
0022-2860/© 2015 Elsevier B.V. All rights reserved.

D. Dong et al. / Journal of Molecular Structure 1104 (2016) 58e62
59
Table 1
2. Experimental section
Crystallographic data and structure refinement for compound 1.
2.1. General procedures
Formula
Fw
C27H24Br2ClMnN4O7
766.71
Crystal system
Space group
a, Å
Tetragonal
P43212
16.5697(5)
21.9035(15)
6013.7(5)
8
The reagents were obtained from commercial sources and used
without further purification. Elemental analyses were performed
on an Elementar Vario ELIII analyzer. IR spectra were recorded
using KBr pellets on a Vector 22 Bruker spectrophotometer in the
4000e400 cmꢀ1 regions. The UVeVis diffuse reflectance spectra
were recorded with a JASCO V-570 UVeViseNIR spectrophotom-
eter in the 300e800 nm. Cyclic voltammetry (CV) measurements
were carried out on a BAS 100 W system in a three-electrode cell
with a pure N2 gas inlet and outlet. Temperature-dependent mag-
netic measurements were carried out on a Quantum Design SQUID
MPMS-5 magnetometer with an applied field of 1 kOe, and
diamagnetic corrections were made with Pascal's constants.
c, Å
V, Å3
Z
Dc, g/cm3
1.694
3.237
m
(Mo Ka), mmꢀ1
Crystal size, mm3
0.40 ꢂ 0.10 ꢂ 0.08
1.54, 27.50
26816
6847 (0.0653)
4304
379
99.2
0.0817, 0.2047
0.1308, 0.2395
ꢀ0.02(2)
1.015
ꢁ
qmin, qmax,
No. total reflns.
No. uniq. reflns (Rint
)
No. obs. [I ꢃ 2
s(I)]
No. params
Completeness to theta ¼ 27.50, %
R1, wR2 [I ꢃ 2
s
(I)]
R1, wR2 (all data)
Absolute structure parameter
GOF
2.2. Synthesis of the Schiff-base ligand N,N-bis(5-
Bromosalicylidene)ethane-1,2-diamine (5-Brsalen)
R1 ¼ S (jF0jejFCj)/S jF0j; wR2 ¼ [S w (jF0jejFCj)2/S w F02]1/2
.
The tetradentate Schiff base ligand was prepared by the
condensation of 5-Bromosalicylaldehyde (2.01 g, 10 mmol) and 1,2-
ethanediamine (0.30 g, 5 mmol) in methanol (10 mL) as reported
earlier [30].
Table 2. CCDC 1026479 contains the supplementary crystallo-
graphic data for this paper. These data can be obtained free of
charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or
from the Cambridge Crystallographic Data Centre, 12, Union Road,
Cambridge CB21EZ, UK; Email: deposit@ccdc.cam.ac.uk).
2.3. Synthesis of [MnIII(5-Brsalen)(H2O)]ClO4 (5-BrsalenMn)
The manganese(III) complex was obtained by mixing man-
ganese(III) acetate dihydrate (5.0 mmol, 1.34 g) and 5-Brsalen
(5.0 mmol, 2.13 g) in methanol (200 mL) and anhydrous sodium
perchlorate (7.5 mmol, 0.92 g) in water (80 mL). After evaporation
to 40 mL and cooling, the resulting black crystals were collected by
suction filtration [31]. Anal. Calcd for C16H14N2O7Br2ClMn: C, 32.22;
H, 2.73; N, 4.70%. Found: C, 32.17; H, 2.70; N, 4.75%.
3. Results and discussion
3.1. Crystal structures
Single-crystal X-ray diffraction analysis revealed that compound
1 crystallizes in the tetragonal chiral space group P43212. The
crystal structure comprised one [MnIII(5-Brsalen)(4,4-bipy)]þ
cation, one uncoordinated methanol molecule and one perchlorate
anion. As shown in Fig. 1, each manganese (III) anion is six-
coordinate octahedral being bonded to four atoms of 5-Brsalen
ligand in an equatorial plane and two nitrogen atoms from a 4,4-
bipyridine ligand in axial positions. Each 4,4-bipyridine molecule
links the MnIII(5-Brsalen) moieties result in the one-dimensional
polymeric structure. The bond lengths in the equatorial plane fall
in the range of 1.889(5)e1.895(6) Å for MneO, 1.978(6)e1.978(7) Å
for MneN, while axial MneN distances are in the range of
2.346(6)e2.362(6) Å. Selected bond lengths and angles are sum-
marized in Table 2. The axial bonds are significantly longer than the
equatorial bonds, as expected for the JahneTeller distortion of Mn
ions with a þ3 oxidation state. The intrachain Mn/Mn distance is
2.4. Synthesis of [MnIII(5-Brsalen)(4,4-bipy)]·ClO4·CH3OH (1)
A solution of [MnIII(5-Brsalen)H2O]ClO4 (0.1 mmol, 0.060 g) and
4,4-bipyridine (0.1 mmol, 0.016 g) in CH3OH solution (20 mL) was
stirred for 2 h at room temperature, and then filtered, and the
filtrate was left at room temperature in the dark room for evapo-
ration. After one week, the dark-brown crystals was collected by
suction filtration, washed with water, and air-dried. Yield: 43%.
Elemental analysis for compound 1: Calc (found) for
C
27H24Br2ClMnN4O7: %C 42.30 (42.36), %N 7.31 (7.35), %H 3.16
(3.18). IR (solid KBr pellet
n
/cmꢀ1): 3441 br, 3082 w, 3048 w,
2965 w, 2826 w, 2854 w, 2802 w, 1624 s, 1532 w, 1451 s, 1407 m,
1371 m, 1277 m,1179 w,1092 s,1005 w, 975 w, 832 w, 807 w, 690 w,
621 w, 479 w, 463 w.
2.5. X-ray crystallography
Table 2
Selected bond lengths (Å) and angles (ꢁ) for complex 1.
The data were collected at a temperature of 293
Bruker Smart APEX Ⅱ Xediffractometer equipped with graphite
monochromated MoeK radiation (
¼ 0.71073 Å) using the
2 K on a
Mn(1)-O(1)
Mn(1)-O(2)
Mn(1)-N(1)
Br(1)-C(4)
1.889(5)
1.895(6)
1.978(7)
1.907(10)
Mn(1)-N(2)
Mn(1)-N(3)
Mn(1)-N(4)#1
Br(2)-C(13)
1.978(6)
2.346(6)
2.362(6)
1.910(9)
a
l
SMART and SAINT programs. Indexing and unit cell refinement
were based on all observed reflections from those 72 frames. The
structure was solved in the space group P43212 by direct method
and refined by the fullematrix leastesquares fitting on F2 using
SHELXTLe97 [32]. All nonehydrogen atoms were refined aniso-
tropically and the hydrogen atoms isotropically in theoretical po-
sitions. The final cycle of full-matrix least-squares refinement was
O(1)-Mn(1)-O(2)
O(1)-Mn(1)-N(2)
O(2)-Mn(1)-N(2)
O(1)-Mn(1)-N(1)
O(2)-Mn(1)-N(1)
N(2)-Mn(1)-N(1)
O(1)-Mn(1)-N(3)
O(2)-Mn(1)-N(3)
97.8(2)
172.2(3)
89.4(3)
91.0(2)
171.2(3)
81.8(3)
88.0(2)
88.9(2)
N(2)-Mn(1)-N(3)
N(1)-Mn(1)-N(3)
95.0(2)
91.6(3)
86.6(2)
88.6(2)
90.7(2)
91.7(3)
173.7(2)
O(1)-Mn(1)-N(4)#1
O(2)-Mn(1)-N(4)#1
N(2)-Mn(1)-N(4)#1
N(1)-Mn(1)-N(4)#1
N(3)-Mn(1)-N(4)#1
based on number of observed reflections (I > 2s(I)). The crystal data
and structure refinement of compound 1 is summarized in Table 1.
Selected bond lengths (Å) and bond angles (ꢁ) for 1 is listed in
Symmetry transformations used to generate equivalent atoms: #1 y þ 1, x, ez.

60
D. Dong et al. / Journal of Molecular Structure 1104 (2016) 58e62
Fig. 1. Side view of a 1-D chain along the a-axis. All the H atoms, perchlorate anions and methanol molecules are omitted for clarity. Atomic scheme: Mn(III), turquoise; C, light gray;
N, blue; Br, violet; O, red. (For interpretation of the references to color in this figure legend, the reader is referred to the web version of this article.)
11.768 Å.
In the compound, there is considerable
4000 to 400 cmꢀ1, as shown in Fig. 4. The absorption bands around
3441 cmꢀ1 corresponds to the vibrations of OeH stretching of
methanol molecule. The bands at the region of 3082e2800 cmꢀ1
are assigned to the aromatic and aliphatic CeH stretching vibra-
tions, and the strong bands at the region of 1532e1371 cmꢀ1 are
assigned to the aromatic C]C stretching vibrations. The sharp
peaks at 1624 related to the C]N groups in compound 1, while the
strong band at 1451 attributed to the aromatic C]C stretching vi-
brations. The bands at 1277 cmꢀ1 is assigned to the AreO stretching
vibrations, while the strong band at 1092 cmꢀ1 give evidence for
the presence of ionic perchlorate in each of the compound [30]. The
bands at the region of 1005e621 cmꢀ1 are assigned to the aromatic
and aliphatic CeH bending vibrations. In addition, the band at
about 479 and 463 cmꢀ1 in the compound are assigned MꢀO and
MꢀN stretching vibrations of 5-Brsalen, respectively [35].
p
-stacking interactions
with the centroid distance of 3.995 and 3.770 Å between the
neighboring chains of the aromatic rings of 4,4-bipyridine and 5-
Brsalen molecules (Fig. 2). On the basis of these connection
modes, the mutual parallel 1D chains of each layer are interwoven
perpendicularly to generate a two-dimensional supramolecular
network (Fig. 3a), which form the left-handed helical character
running along a crystallographic 43 axis in the c direction (Fig. 3b,
c). Notably, the compound 1 has the same handedness and the
refined value of the Flack parameter (ꢀ0.01(2)) shows that each
crystal of the chiral framework phase grows as one single enan-
tiomer, with a homochiral character for the helix winding. In
general, two key factors are necessary to generate a homochiral
coordination polymer from an achiral ligand without any chiral
auxiliary [33,34]. This means that not only the achiral components
must assemble into chiral units, but also these chiral units homo-
chirally aggregate. So it is difficult to construct the homochiral helix
from achical components.
3.3. UVeVis spectrum and electrochemical property
UVevis absorption spectrum is carried out for the complex 1 in
CH3CN solution to investigate the light absorption characteristics
and the result is shown in Fig. 5. As can be seen, the complex 1
shows five absorption bands at 300e800 nm. The bands at ca. 409
and 354 nm may be due to ligand-to-metal charge transfer arising
from 5-Brsalen ligand. The bands at around 316, 283 and 238 nm
which appeared without considerable shifting compared to their
3.2. Infrared spectroscopy
The IR spectrum of compound 1 was recorded in the region from
parent ligands were assigned to the
p/p* transitions of the 5-
Brsalen and 4,4-bipy ligands associated with the azomethine and
aromatic ring systems, respectively [36,37]. Analytical data were
also in good agreement with the proposed structures.
Cyclic voltammetry (CV) was carried out on 1 in MeCN solution
at 293 K. The electrochemical behavior of 1 was examined in
acetonitrile containing 0.1
M tetra-n-butylammonium hexa-
flourophosphate (Bu4NPF6) as a supporting electrolyte in a con-
ventional three electrode configuration using a glassy carbon
working electrode, Pt auxiliary electrode and Ag/AgCl reference
electrode. A representative cyclic voltammogram of 1 is shown in
Fig. 6, consisting of a reversible MnIII/MnII reduction at ꢀ0.34 V, and
a quasi-reversible MnIII/MnIV metal-centered oxidation at þ1.34 V
versus aqueous Ag/AgCl. Moreover, the potential value for 1 (E1/
2(1) ¼ ꢀ0.18 V, E1/2(2) ¼ 0.60 V), suggests relative stabilization of
the MnII state and destabilization of the MnIV state, which is
comparable to the closely related manganese(III) complexes
[36,37].
3.4. Magnetic properties
Fig. 2. Formation of two-dimensional supramolecular network by
p-stacking in-
teractions in compound 1. All the H atoms, perchlorate anions and methanol molecules
are omitted for clarity. Atomic scheme: Mn(III), turquoise; C, light gray; N, blue; Br,
violet; O, red. (For interpretation of the references to color in this figure legend, the
reader is referred to the web version of this article.)
The magnetic susceptibility of compound 1 was measured in the
temperature range 2e300 K at a field strength of 1000 Oe. The
temperature dependent magnetic behavior of 1 is shown in Fig. 7 as

D. Dong et al. / Journal of Molecular Structure 1104 (2016) 58e62
61
Fig. 3. (a) Perspective views of the multilayer chains of polyhedral scheme for 1 along the a-axis: First layer, yellow; Second layer, light yellow; third layer, turquoise; fourth layer,
light turquoise. The hydrogen atoms, perchlorate anions and methanol molecules have been omitted for clarity. (b) Ball and stick representation of compound 1 viewed the helices
along the c axis. The hydrogen atoms, perchlorate anions and methanol molecules have been omitted for clarity. (c) Perspective and space-filling viewed the helices in 1 along the c
axis. The hydrogen atoms, anions, solvent and 4,4-bipy molecules are omitted for clarity. Atomic scheme: Mn(III), turquoise; C, light gray; N, blue; Br, violet; O, red. (For inter-
pretation of the references to color in this figure legend, the reader is referred to the web version of this article.)
c
T versus T plots. The c
T value (2.93 cm3 molꢀ1 K) at 300 K for the
compound is lower than the calculated value (3.0 cm3 molꢀ1 K) for
1.00
0.95
0.90
0.85
0.80
0.75
the uncoupled spins (S ¼ 2) with g ¼ 2. With a decrease of tem-
perature from 300 K, the value of
cT decreases very slowly to
2.85 cm3 molꢀ1 K at 10 K. On further lowering of the temperature,
T decreases sharply to 1.41 cm3 molꢀ1 K at 2.0 K. In most possible,
the drop of magnetic susceptibility in T form results from
c
c
spineorbit (SO) coupling of Mn(III) ion, since the neighboring
Mn(III) ions are separated long distance. This temperature depen-
dent magnetic behavior indicates weak antiferromagnetic inter-
action for the compound 1.
4. Conclusion
4000 3500 3000 2500 2000 1500 1000 500
We have synthesized a novel homochiral manganese (III) Mn(5-
Brsalen) coordination polymer with left-handed helical character
by spontaneous resolution on crystallization by using Mn(5-
Brsalen) and 4,4-bipyridine. In compound 1, each manganese(III)
Wavenumber (cm-1)
Fig. 4. IR spectra of compound 1.
20
15
10
5
2.0
1.5
1.0
0.5
0.0
5-BrsalenMn
MnIII(5-Brsalen)(4,4-bipy) (1)
4,4-bipy
0
-5
-10
-15
-20
200
300
400
500
600
700
800
-0.5
0.0
0.5
1.0
1.5
Wavelength/nm
E/v vs Ag/AgCl
Fig. 5. UVevis absorption spectrum of compound 1, 5-BrsalenMn and 4,4-bipy ligands
Fig. 6. Cyclic voltammogram of compound
100 mV sꢀ1
1 in CH3CN solution. Scan rate at
in CH3CN solution(10ꢀ3 M).
.

62
D. Dong et al. / Journal of Molecular Structure 1104 (2016) 58e62
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This work was partly supported by the NSFC (Grant Nos.
21301023, 21501021, 11474045), the 2014 Program for Liaoning
Excellent Talents in University (Grant No. LJQ2014138), and the
Fundamental Research Funds for the Central Universities (Grant No.
DC201502080305).
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